(R)-N'-(hept-1-en-4-yl)benzohydrazide | 1392047-72-1

• 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: (R)-N'-(hept-1-en-4-yl)benzohydrazide
• 英文别名: N'-[(4R)-hept-1-en-4-yl]benzohydrazide
• CAS: 1392047-72-1
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: DANCOKIFCJURNK-ZDUSSCGKSA-N

物化性质

• 沸点：
  315.3±25.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (R)-N'-(hept-1-en-4-yl)benzohydrazide 在 甲醇 、 samarium diiodide 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 、 mineral oil 为溶剂， 50.0 ℃ 、500.01 kPa 条件下， 反应 48.5h， 生成 (R)-2-丙基哌啶
  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：

  苯甲酸亚丁基酰肼 、 3-溴丙烯 在 C₃₄H₃₂N₂O₂*F₆P^(1-)*H⁽¹⁺⁾ 、 indium 、 水 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 59.0h， 以93%的产率得到(R)-N'-(hept-1-en-4-yl)benzohydrazide
  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

文献信息

• 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.