(S)-N-allyl-N-benzyl-1-(benzyloxymethyl)-2-methylenecyclopentanamine | 1159996-64-1

• 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: (S)-N-allyl-N-benzyl-1-(benzyloxymethyl)-2-methylenecyclopentanamine
• 英文别名: (1S)-N-benzyl-2-methylidene-1-(phenylmethoxymethyl)-N-prop-2-enylcyclopentan-1-amine
• CAS: 1159996-64-1
• 化学式: C₂₄H₂₉NO
• 分子量: 347.5
• InChiKey: OTAIZCGHHLNERZ-XMMPIXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-allyl-N-benzyl-1-(benzyloxymethyl)-2-methylenecyclopentanamine 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以78%的产率得到(S)-1-benzyl-6a-(benzyloxymethyl)-1,2,4,5,6,6a-hexahydrocyclopenta[b]pyrrole
  参考文献：
  名称：

  Synthesis of Boc-protected bicycloproline

  摘要：

  The synthesis of a highly constrained quaternary carbocyclic alpha-amino acid, (+)-N-Boc-bicycloproline, has been achieved starting from sodium cyclopentadienylide. Key steps include a rhodium-catalyzed nitrenoid C-H insertion to install the tert-alkylamine and a ring-closing metathesis reaction to form the pyrrolidine ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.092
• 作为产物：
  描述：

  (R)-2-(allyl(benzyl)amino)-2-(benzyloxymethyl)cyclopentanone 、 甲基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以88%的产率得到(S)-N-allyl-N-benzyl-1-(benzyloxymethyl)-2-methylenecyclopentanamine
  参考文献：
  名称：

  Synthesis of Boc-protected bicycloproline

  摘要：

  The synthesis of a highly constrained quaternary carbocyclic alpha-amino acid, (+)-N-Boc-bicycloproline, has been achieved starting from sodium cyclopentadienylide. Key steps include a rhodium-catalyzed nitrenoid C-H insertion to install the tert-alkylamine and a ring-closing metathesis reaction to form the pyrrolidine ring. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.092

文献信息

• Synthesis of Boc-protected bicycloproline
  作者：Sujeewa Ranatunga、Juan R. Del Valle

  DOI：10.1016/j.tetlet.2009.03.092

  日期：2009.5

  The synthesis of a highly constrained quaternary carbocyclic alpha-amino acid, (+)-N-Boc-bicycloproline, has been achieved starting from sodium cyclopentadienylide. Key steps include a rhodium-catalyzed nitrenoid C-H insertion to install the tert-alkylamine and a ring-closing metathesis reaction to form the pyrrolidine ring. (C) 2009 Elsevier Ltd. All rights reserved.