(S)-N'-[1-(3-chlorophenyl)but-3-enyl]benzohydrazide | 1242159-30-3

• 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: (S)-N'-[1-(3-chlorophenyl)but-3-enyl]benzohydrazide
• 英文别名: N'-[(1S)-1-(3-chlorophenyl)but-3-enyl]benzohydrazide
• CAS: 1242159-30-3
• 化学式: C₁₇H₁₇ClN₂O
• 分子量: 300.788
• InChiKey: GTBOSTBTMNRAHU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 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：

  (S)-N'-[1-(3-chlorophenyl)but-3-enyl]benzohydrazide 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-1-(3-Chlorophenyl)but-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’-(3-chlorophenylmethylene)benzohydrazide 、 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90%的产率得到(S)-N'-[1-(3-chlorophenyl)but-3-enyl]benzohydrazide
  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

• 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。
• 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
  作者：Fengnu Piao、Mithilesh Kumar Mishra、Doo Ok Jang

  DOI：10.1016/j.tet.2012.06.061

  日期：2012.9

  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.