Octet / Reactions

Enamine Formation

Included in Reactions.

Carbonyl

Source Details

Id

enamine-formation

Name
{
  "en": "Enamine Formation",
  "ar": "Enamine تكوين",
  "cs": "Enamine Tvorba",
  "da": "Enamine Dannelse",
  "de": "Enamine Bildung",
  "el": "Εναμίνη Σχηματισμός",
  "es-419": "Formación de énamine",
  "es-ES": "Formación de énamine",
  "es": "Formación de énamine",
  "fi": "Enamine Muodostus",
  "fr": "Formation d'énamine",
  "he": "Enamine יצירה",
  "hr": "Enamine Stvaranje",
  "hu": "Enamban Képződés",
  "id": "Pembentukan Enamina",
  "it": "Formazione di énamine",
  "ja": "エナミン形成",
  "ko": "엔아민 형성",
  "lv": "Enamine Veidosanas",
  "nb": "Enamine Dannelse",
  "nl": "Enamine Vorming",
  "pl": "Enamine Tworzenie",
  "pt-BR": "Formação de énamine",
  "pt-PT": "Formação de énamine",
  "ro": "Formare de énamine",
  "ru": "Enamine Образование",
  "sk": "Enamine Tvorba",
  "sl": "Enamine Tvorba",
  "sv": "Enamine Bildning",
  "th": "การเกิดอีนามีน",
  "tr": "Enamiçinde Oluşumu",
  "uk": "Enamine Утворення",
  "vi": "Tạo enamine",
  "zh-Hans": "烯胺形成",
  "zh": "烯胺形成"
}
Type
{
  "en": "Carbonyl",
  "ar": "كربونيل",
  "cs": "Karbonylová",
  "da": "Carbonyl",
  "de": "Carbonyl",
  "el": "Καρβονύλιο",
  "es-419": "Carbonilo",
  "es-ES": "Carbonilo",
  "es": "Carbonilo",
  "fi": "Karbonyyli",
  "fr": "Carbonyle",
  "he": "קרבוניל",
  "hr": "Karbonilna",
  "hu": "Karbonil",
  "id": "Karbonil",
  "it": "Carbonile",
  "ja": "カルボニル",
  "ko": "카르보닐",
  "lv": "Karbonilgrupa",
  "nb": "Karbonyl",
  "nl": "Carbonyl",
  "pl": "Karbonylowa",
  "pt-BR": "Carbonila",
  "pt-PT": "Carbonila",
  "ro": "Carbonil",
  "ru": "Карбонильные",
  "sk": "Karbonylová",
  "sl": "Karbonilna",
  "sv": "Karbonyl",
  "th": "คาร์บอนิล",
  "tr": "Karbonil",
  "uk": "Карбонільні",
  "vi": "Cacbonyl",
  "zh-Hans": "羰基",
  "zh": "羰基"
}
Starting Material

CC(=O)CC

Product

CC(=CN(C)C)C

Reagents

R₂NH (2° amine), acid catalyst

Conditions
{
  "en": "Remove water (Dean-Stark)",
  "ar": "Remove الماء (Dean-Stark)",
  "cs": "Remove voda (Dean-Stark)",
  "da": "Remove vand (Dean-Stark)",
  "de": "Remove Wasser (Dean-Stark)",
  "el": "Απομάκρυνση νερού (Dean-Stark)",
  "es-419": "Remove agua (Dean-Stark)",
  "es-ES": "Remove agua (Dean-Stark)",
  "es": "Remove agua (Dean-Stark)",
  "fi": "Remove vesi (Dean-Stark)",
  "fr": "Remove eau (Dean-Stark)",
  "he": "Remove מים (Dean-Stark)",
  "hr": "Remove voda (Dean-Stark)",
  "hu": "Víz eltávolítása (Dean-Stark)",
  "id": "Hilangkan air (Dean-Stark)",
  "it": "Remove acqua (Dean-Stark)",
  "ja": "水を除去(Dean-Stark)",
  "ko": "물 제거(Dean-Stark)",
  "lv": "Remove udens (Dean-Stark)",
  "nb": "Remove vann (Dean-Stark)",
  "nl": "Verwijder water (Dean-Stark)",
  "pl": "Remove woda (Dean-Stark)",
  "pt-BR": "Remove água (Dean-Stark)",
  "pt-PT": "Remove água (Dean-Stark)",
  "ro": "Remove apă (Dean-Stark)",
  "ru": "Remove вода (Dean-Stark)",
  "sk": "Remove voda (Dean-Stark)",
  "sl": "Remove voda (Dean-Stark)",
  "sv": "Remove vatten (Dean-Stark)",
  "th": "กำจัดน้ำ (Dean-Stark)",
  "tr": "Suyu uzaklaştır (Dean-Stark)",
  "uk": "Remove вода (Dean-Stark)",
  "vi": "Loại nước (Dean-Stark)",
  "zh-Hans": "除水(Dean-Stark)",
  "zh": "除水(Dean-Stark)"
}
Mechanism
[
  {
    "smiles": "CC(=O)CC",
    "description": {
      "en": "2-Butanone (ketone)",
      "ar": "2-Butanone (كيتون)",
      "cs": "2-Butanone (keton)",
      "da": "2-Butanone (keton)",
      "de": "2-Butanone (Keton)",
      "el": "2-Butanένα (κετόνη)",
      "es-419": "2-Butanone (cetona)",
      "es-ES": "2-Butanone (cetona)",
      "es": "2-Butanone (cetona)",
      "fi": "2-Butanone (ketoni)",
      "fr": "2-Butanone (cétone)",
      "he": "2-Butanone (קטון)",
      "hr": "2-Butanone (keton)",
      "hu": "2-Butanegy (keton)",
      "id": "2-Butanon (keton)",
      "it": "2-Butanone (chetone)",
      "ja": "2-ブタノン(ケトン)",
      "ko": "2-뷰타논(케톤)",
      "lv": "2-Butanone (ketons)",
      "nb": "2-Butanone (keton)",
      "nl": "2-Butanone (keton)",
      "pl": "2-Butanone (keton)",
      "pt-BR": "2-Butanone (cetona)",
      "pt-PT": "2-Butanone (cetona)",
      "ro": "2-Butanone (cetonă)",
      "ru": "2-Butanone (кетон)",
      "sk": "2-Butanone (keton)",
      "sl": "2-Butanone (keton)",
      "sv": "2-Butanone (keton)",
      "th": "2-บิวทาโนน (คีโตน)",
      "tr": "2-Butanbir (ketüzerinde)",
      "uk": "2-Butanone (кетон)",
      "vi": "2-butanone (xeton)",
      "zh-Hans": "2-丁酮(酮)",
      "zh": "2-丁酮(酮)"
    }
  },
  {
    "smiles": "CC(=CN(C)C)C",
    "description": {
      "en": "Enamine (N analog of enol)",
      "ar": "Enamine (N نظير من إينول)",
      "cs": "Enamine (N analog z enol)",
      "da": "Enamin (N-analog af enol)",
      "de": "Enamin (N-Analogon von Enol)",
      "el": "Εναμίνη (N analog της eόχιl)",
      "es-419": "Enamina (análogo N del enol)",
      "es-ES": "Enamina (análogo N del enol)",
      "es": "Enamina (análogo N del enol)",
      "fi": "Enamiini (enolin N-analogi)",
      "fr": "Énamine (analogue N de l’énol)",
      "he": "Enamine (N אנלוג של אנול)",
      "hr": "Enamine (N analog od enol)",
      "hu": "Enamban (N analog of enbancsl)",
      "id": "Enamina (analog N dari enol)",
      "it": "Enammina (analogo N dell’enolo)",
      "ja": "エナミン(エノールのN類縁体)",
      "ko": "엔아민(엔올의 N 유사체)",
      "lv": "Enamine (N analog nav enol)",
      "nb": "Enamin (N-analog av enol)",
      "nl": "Enamine (N-analoog van enol)",
      "pl": "Enamine (N analog z enol)",
      "pt-BR": "Enamina (análogo N do enol)",
      "pt-PT": "Enamina (análogo N do enol)",
      "ro": "Enamină (analog N al enolului)",
      "ru": "Enamine (N analog из enol)",
      "sk": "Enamine (N analog z enol)",
      "sl": "Enamine (N analog od enol)",
      "sv": "Enamin (N-analog till enol)",
      "th": "อีนามีน (อนาล็อก N ของอีนอล)",
      "tr": "Enamiçinde (N analog eyokl)",
      "uk": "Enamine (N analog з enol)",
      "vi": "Enamine (chất tương tự enol có N)",
      "zh-Hans": "烯胺(烯醇的 N 类似物)",
      "zh": "烯胺(烯醇的 N 类似物)"
    }
  }
]
Tips
[
  {
    "en": "Secondary amine + ketone → Enamine",
    "ar": "ثانوي أمين + كيتون → Enamine",
    "cs": "Sekundarni amin + keton → Enamine",
    "da": "Sekundær amin + keton → Enamine",
    "de": "Sekundär Amin + Keton → Enamine",
    "el": "Δεύτεροary αμίνη + κετόνη → Εναμίνη",
    "es-419": "Secundario amina + cetona → Enamine",
    "es-ES": "Secundario amina + cetona → Enamine",
    "es": "Secundario amina + cetona → Enamine",
    "fi": "Sekundäärinen amiini + ketoni → Enamine",
    "fr": "Secondaire amine + cétone → Enamine",
    "he": "שניוני אמין + קטון → Enamine",
    "hr": "Sekundarni amin + keton → Enamine",
    "hu": "Másodikary amban + keton → Enamban",
    "id": "Amina sekunder + keton → enamina",
    "it": "Secondario ammina + chetone → Enamine",
    "ja": "第二級アミン + ケトン → エナミン",
    "ko": "2차 아민 + 케톤 → 엔아민",
    "lv": "Sekundarais amins + ketons → Enamine",
    "nb": "Sekundær amin + keton → Enamine",
    "nl": "Secundair amine + keton → Enamine",
    "pl": "Drugorzędowy amina + keton → Enamine",
    "pt-BR": "Secundário amina + cetona → Enamine",
    "pt-PT": "Secundário amina + cetona → Enamine",
    "ro": "Secundar amină + cetonă → Enamine",
    "ru": "Вторичный амин + кетон → Enamine",
    "sk": "Sekundarny amin + keton → Enamine",
    "sl": "Sekundarni amin + keton → Enamine",
    "sv": "Sekundär amin + keton → Enamine",
    "th": "เอมีนทุติยภูมิ + คีโตน → อีนามีน",
    "tr": "İkiçindeciary amiçinde + ketüzerinde → Enamiçinde",
    "uk": "Вторинний амін + кетон → Enamine",
    "vi": "Amin bậc hai + xeton → enamine",
    "zh-Hans": "仲胺 + 酮 → 烯胺",
    "zh": "仲胺 + 酮 → 烯胺"
  },
  {
    "en": "Enamines are nucleophilic at β-carbon",
    "ar": "Enamines هي نيوكليوفيلي عند β-كربون",
    "cs": "Enamines jsou nukleofilni pri β-uhlik",
    "da": "Enamines er nucleophilic at β-kulstof",
    "de": "Enamines sind nucleophilic at β-Kohlenstoff",
    "el": "Enαμίνες are πυρηνόφιλο σε β-άνθρακας",
    "es-419": "Enamines are nucleofílico a β-carbon",
    "es-ES": "Enamines are nucleofílico a β-carbon",
    "es": "Enamines are nucleofílico a β-carbon",
    "fi": "Enamines ovat nucleophilic at β-hiili",
    "fr": "Enamines are nucléophile à β-carbon",
    "he": "Enamines הם נוקלאופילי ב β-פחמן",
    "hr": "Enamines su nukleofilno pri β-ugljik",
    "hu": "Enambanbancsk are nukleofil nál β-szén",
    "id": "Enamina bersifat nukleofilik pada β-karbon",
    "it": "Enamines are nucleofilo a β-carbon",
    "ja": "エナミンはβ-炭素で求核的",
    "ko": "엔아민은 β-탄소에서 친핵성임",
    "lv": "Enamines ir nukleofils pie β-ogleklis",
    "nb": "Enamines er nucleophilic at β-karbon",
    "nl": "Enamines zijn nucleophilic at β-koolstof",
    "pl": "Enamines sa nukleofilowy w β-wegiel",
    "pt-BR": "Enamines are nucleofílico a β-carbon",
    "pt-PT": "Enamines are nucleofílico a β-carbon",
    "ro": "Enamines are nucleofil la β-carbon",
    "ru": "Enamines являются нуклеофильный при β-углерод",
    "sk": "Enamines su nukleofilny pri β-uhlik",
    "sl": "Enamines so nukleofilno pri β-ogljik",
    "sv": "Enamines är nucleophilic at β-kol",
    "th": "อีนามีนเป็นนิวคลีโอไฟล์ที่คาร์บอนตำแหน่ง β",
    "tr": "Enamiçindeler are nükleofilik de β-karbüzerinde",
    "uk": "Enamines є нуклеофільний за β-вуглець",
    "vi": "Enamine có tính ái nhân tại β-carbon",
    "zh-Hans": "烯胺在 β-碳上具有亲核性",
    "zh": "烯胺在 β-碳上具有亲核性"
  },
  {
    "en": "Stork enamine synthesis: enamine + electrophile → α-substituted ketone",
    "ar": "Stork enamine تحضير: enamine + إلكتروفيل → α-مستبدل كيتون",
    "cs": "Stork enamine synteza: enamine + elektrofil → α-substituovany keton",
    "da": "Stork enamine synthesis: enamine + electrophile → α-substitueret keton",
    "de": "Stork enamine synthesis: enamine + electrophile → α-substituiert Keton",
    "el": "Stήk εναμίνη σύνθεση: εναμίνη + ηλεκτρονιόφιλο → α-υποκατεστημένο κετόνη",
    "es-419": "Stork enamine synthesis: enamine + electrophile → α-substituted cetona",
    "es-ES": "Stork enamine synthesis: enamine + electrophile → α-substit...
Related Reactions

aldol-addition

Is Free

false