benzoic acid N'-(1-phenylbut-3-enyl)hydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzoic acid N'-(1-phenylbut-3-enyl)hydrazide
• 英文别名: (S)-N'-(1-phenylbut-3-enyl)benzohydrazide；N'-(1-phenylbut-3-enyl)benzohydrazide；N'-[(1S)-1-phenylbut-3-enyl]benzohydrazide
• 化学式: C₁₇H₁₈N₂O
• 分子量: 266.343
• InChiKey: IZXAYNNDPCGKII-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzoic acid N'-(1-phenylbut-3-enyl)hydrazide 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-1-phenylbut-3-en-1-amine
  参考文献：
  名称：

  RETRACTED: Asymmetric synthesis of highly enantioenriched 2-substituted piperidines and 6-substituted piperidine-2-ones by a combination enantioselective hydrazone allylation with ring closing metathesis

  摘要：

  An efficient method for the asymmetric synthesis of highly optically pure 2-substituted piperidines and 6-substituted piperidine-2-ones from aldehydes was developed by a sequence of enantioselective hydrazone allylation and ring closing metathesis. This method was found to be effective for a variety of substrates, showing substrate generality. The method's synthetic utility was illustrated in concise synthesis of the alkaloid (R)-(-)-coniine. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.061
• 作为产物：
  描述：

  N-苯甲酰基-N'-苄亚基肼 、 3-溴丙烯 在 C₃₄H₃₂N₂O₂*F₆P^(1-)*H⁽¹⁺⁾ 、 indium 作用下， 以 甲醇 为溶剂， 反应 10.17h， 以94%的产率得到benzoic acid N'-(1-phenylbut-3-enyl)hydrazide
  参考文献：
  名称：

  使用质子化手性胺铟介导的 N-苯甲酰腙催化对映选择性烯丙基化

  摘要：

  开发了一种催化对映选择性铟介导的 N-苯甲酰腙与质子化手性胺的烯丙基化反应，提供具有极高对映选择性和化学产率的对映体富集的高烯丙基胺。

  DOI：

  10.1021/ja1035336

文献信息

• Toward a Versatile Allylation Reagent:  Practical, Enantioselective Allylation of Acylhydrazones Using Strained Silacycles
  作者：Richard Berger、Philippe M. A. Rabbat、James L. Leighton

  DOI：10.1021/ja035001g

  日期：2003.8.1

  A highly practical method for the enantioselective allylation of acylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of acylhydrazones to give the hydrazide products with good enantioselectivity (83-89% ee, typically). It has been demonstrated that the products may be isolated without chromatography by recrystallization in >/=98% ee.

  已经开发了一种用于酰基腙的对映选择性烯丙基化的非常实用的方法。先前报道的应变硅环试剂 1 与多种酰基腙反应，得到具有良好对映选择性（通常为 83-89% ee）的酰肼产物。已经证明可以通过在≥98% ee中重结晶而无需色谱法来分离产物。
• Indium-Mediated Catalytic Enantioselective Allylation of <i>N</i>-Benzoylhydrazones Using a Protonated Chiral Amine
  作者：Sung Jun Kim、Doo Ok Jang

  DOI：10.1021/ja1035336

  日期：2010.9.8

  A catalytic enantioselective indium-mediated allylation of N-benzoylhydrazones in conjunction with a protonated chiral amine affording enantioenriched homoallylic amines with an extremely high level of enantioselectivity and chemical yield was developed.

  开发了一种催化对映选择性铟介导的 N-苯甲酰腙与质子化手性胺的烯丙基化反应，提供具有极高对映选择性和化学产率的对映体富集的高烯丙基胺。
• Indium(I)-Catalyzed Asymmetric Allylation, Crotylation, and α-Chloroallylation of Hydrazones with Rare Constitutional and High Configurational Selectivities
  作者：Ananya Chakrabarti、Hideyuki Konishi、Miyuki Yamaguchi、Uwe Schneider、Shū Kobayashi

  DOI：10.1002/anie.200906308

  日期：2010.3.1

  The hydra‐zone: The first example of asymmetric InI catalysis had been developed. InI combined with a chiral semicorrin ligand (L*) is an effective catalyst for enantioselective allylation, crotylation, and α‐chloroallylation of hydrazones. In the two latter cases, CC bond formations proceeded with high selectivity where both reactive aliphatic CCl and aromatic OH bonds were tolerated.

  区：开发了不对称In I催化的第一个例子。InI与手性半corrin配体（L *）结合是hydr的对映选择性烯丙基化，丁烯酰化和α-氯代烯丙基化的有效催化剂。在后两种情况下，CC键的形成过程具有很高的选择性，同时可以容忍反应性脂族CCl和芳族OH键。
• Chiral sulfur derivatives in the allylation of acyl hydrazones: C2-symmetric bis-sulfinamides as enhanced chiral organic promoters.
  作者：Inmaculada Fernández、Ana Alcudia、Beatrice Gori、Victoria Valdivia、Rocío Recio、María Victoria García、Noureddine Khiar

  DOI：10.1039/c0ob00078g

  日期：——

  Monosulfinamides and C2-symmetric bis-sulfinamides are convenient neutral chiral promoters in the allylation of acyl hydrazones, the nature of the spacer and the substituent at the sulfinyl sulfur are key elements for the enantioselectivity of the process.

  在酰基肼的烯丙基化过程中，单亚磺酰胺和 C2 对称双亚磺酰胺是一种方便的中性手性促进剂，间隔物的性质和亚磺酰基硫上的取代基是该过程对映选择性的关键因素。
• The sulfinyl moiety in Lewis base-promoted allylations
  作者：J. Robin Fulton、Lamin M. Kamara、Simon C. Morton、Gareth J. Rowlands

  DOI：10.1016/j.tet.2009.09.042

  日期：2009.11

  By employing Senanayake's oxathiazolidine-2-oxide reagent, a collection of sulfinamides was prepared and provided the first examples of sulfinamides promoting the allylation of benzaldehyde and N-benzoylhydrazones with allyltrichlorosilane. The optimum sulfinamide-derived Lewis base promoter displays comparable activity to the best sulfinyl-based Lewis bases reported. The use of bis-sulfoxides is also discussed. (C) 2009 Elsevier Ltd. All rights reserved.