(E)-1-(1-Pyrrolidino)-1-nonene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (E)-1-(1-Pyrrolidino)-1-nonene
• 英文别名: (E)-1-pyrrolidino-1-nonene；1-[(E)-non-1-enyl]pyrrolidine
• 化学式: C₁₃H₂₅N
• 分子量: 195.348
• InChiKey: LYFHDTDDTOQRRU-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(1-Pyrrolidino)-1-nonene 在 sodium hydroxide 、 diisopinocamphenylboron chloride 、 双氧水 作用下， 生成 (R)-1-(1-Pyrrolidino)-2-nonanol 、 (S)-1-(1-Pyrrolidino)-2-nonanol
  参考文献：
  名称：

  合成中的硼烷。1.β-氨基醇的不对称合成。高对映体纯度将烯胺轻松转化为相应的β-氨基醇

  摘要：

  醛烯胺与d Ipc 2 BH在0°C下不对称氢硼化，然后用NaOH / H 2 O 2氧化，得到相应的β-氨基醇，收率高，对映体过量高。

  DOI：

  10.1016/s0040-4039(00)61541-1
• 作为产物：
  描述：

  四氢吡咯 、 壬醛 在 calcium hydride 作用下， 以 环己烷 为溶剂， 以90%的产率得到(E)-1-(1-Pyrrolidino)-1-nonene
  参考文献：
  名称：

  A Facile New Synthesis of Aldehyde Enamines in High Yield and High Purity

  摘要：

  Aldehyde enamines were synthesized in excellent yield and purity by reacting an aldehyde with 2 equivalents of a secondary amine in cyclohexane in the presence of 1.5 equivalents of CaH2. Distilled yields ranged from 65%-92%.

  DOI：

  10.1080/00397919408010154

文献信息

• Boranes in Synthesis. 1. Asymmetric synthesis of β-amino alcohols. A facile conversion of enamines to the corresponding β-amino alcohols in high enantiomeric purity
  作者：Gary B. Fisher、Christian T. Goralski、Lawrence W. Nicholson、Bakthan Singaram

  DOI：10.1016/s0040-4039(00)61541-1

  日期：1993.11

  The asymmetric hydroboration of aldehyde enamines with dIpc2BH at 0 °C, followed by oxidation with NaOH(s)/H2O2, yields the corresponding β-amino alcohols in good yields and high enantiomeric excess.

  醛烯胺与d Ipc 2 BH在0°C下不对称氢硼化，然后用NaOH / H 2 O 2氧化，得到相应的β-氨基醇，收率高，对映体过量高。
• A Facile New Synthesis of Aldehyde Enamines in High Yield and High Purity
  作者：Gary B. Fisher、Lawrence Lee、Frederick W. Klettke

  DOI：10.1080/00397919408010154

  日期：1994.6

  Aldehyde enamines were synthesized in excellent yield and purity by reacting an aldehyde with 2 equivalents of a secondary amine in cyclohexane in the presence of 1.5 equivalents of CaH2. Distilled yields ranged from 65%-92%.
• Boranes in Synthesis. 5. The Hydroboration of Enamines with Mono- and Dialkylboranes. Asymmetric Synthesis of .beta.-Amino Alcohols of Moderate Enantiomeric Purity from Aldehyde Enamines
  作者：Gary B. Fisher、Christian T. Goralski、Lawrence W. Nicholson、Dennis L. Hasha、Donald Zakett、Bakthan Singaram

  DOI：10.1021/jo00112a026

  日期：1995.4

  The hydroboration of both acyclic and cyclic aldehyde and ketone enamines with such representative mono- and dialkylboranes as thexylborane and dicyclohexylborane, followed by an oxidative workup, yields the corresponding beta-amino alcohols in good to excellent isolated yields. The hydroboration of ketone and aldehyde enamines with the asymmetric hydroboration reagents monoisopinocampheylborane ((d)IpcBH(2)) and diisopinocampheylborane ((d)Ipc(2)BH) was also investigated, (d)Ipc(2)BH is highly effective for the asymmetric hydroboration of acyclic aldehyde enamines, such as 1-(4-morpholino)-3-phenyl-1-propene and 1-(1-pyrrolidino)-1-octene. Oxidation of the intermediate trialkylborane furnishes the corresponding beta-amino alcohols in 50-86% ee. The stereogenic center of the carbinol carbon is consistently enriched in the R-enantiomer when (d)Ipc(2)BH prepared from (+)-alpha-pinene is used as the hydroboration reagent. The enantiomeric excesses of the beta-amino alcohols synthesized in this study were determined by HPLC using a chiral stationary phase. The absolute configurations of some of the beta-amino alcohols synthesized in this study were determined by chiral HPLC comparison with authentic beta-amino alcohols prepared from chiral epoxides of known absolute configuration.