5-phenyl-2-(1-phenylethyl)-decahydrobenzo[c]azepin-3-one | 881424-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 5-phenyl-2-(1-phenylethyl)-decahydrobenzo[c]azepin-3-one
• 英文别名: (5R,5aS,9aR)-5-phenyl-2-[(1S)-1-phenylethyl]-4,5,5a,6,7,8,9,9a-octahydro-1H-benzo[c]azepin-3-one
• CAS: 881424-88-0
• 化学式: C₂₄H₂₉NO
• 分子量: 347.5
• InChiKey: CMHULGCQAZMEMY-IITNATTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-phenyl-2-(1-phenylethyl)-decahydrobenzo[c]azepin-3-one 在 palladium dihydroxide lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 20.0~60.0 ℃ 、344.74 kPa 条件下， 反应 53.0h， 生成 5-phenyl-decahydrobenzo[c]azepine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of 4,5,6- and 3,4,5,6-Substituted Azepanes by a Highly Diastereoselective and Enantioselective Lithiation−Conjugate Addition Sequence

  摘要：

  Asymmetric syntheses of 4,5,6- and 3,4,5,6-substituted azepanes have been achieved by highly diastereoselective and enantioselective (-)-sparteine-mediated asymmetric lithiation-conjugate additions of N-Boc-N-(p-methoxyphenyl)-2,3-substituted allylamines to a beta-aryl alpha,beta-unsaturated ester followed by hydrolysis, cyclization, and reduction. Access to the enantiomeric adduct is provided by an invertive lithiation-stannylation-lithiation sequence.

  DOI：

  10.1021/ja057592b
• 作为产物：
  描述：

  反式-4-溴肉桂酸乙酯 在 Raney 2800 nickel 盐酸 、 正丁基锂 、 氢气 、 三甲基铝 、 鹰爪豆碱 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 、 氯仿 、 甲苯 、 苯 为溶剂， 反应 80.25h， 生成 5-phenyl-2-(1-phenylethyl)-decahydrobenzo[c]azepin-3-one
  参考文献：
  名称：

  Asymmetric Synthesis of 4,5,6- and 3,4,5,6-Substituted Azepanes by a Highly Diastereoselective and Enantioselective Lithiation−Conjugate Addition Sequence

  摘要：

  Asymmetric syntheses of 4,5,6- and 3,4,5,6-substituted azepanes have been achieved by highly diastereoselective and enantioselective (-)-sparteine-mediated asymmetric lithiation-conjugate additions of N-Boc-N-(p-methoxyphenyl)-2,3-substituted allylamines to a beta-aryl alpha,beta-unsaturated ester followed by hydrolysis, cyclization, and reduction. Access to the enantiomeric adduct is provided by an invertive lithiation-stannylation-lithiation sequence.

  DOI：

  10.1021/ja057592b

文献信息

• Asymmetric Synthesis of 4,5,6- and 3,4,5,6-Substituted Azepanes by a Highly Diastereoselective and Enantioselective Lithiation−Conjugate Addition Sequence
  作者：Suk Joong Lee、Peter Beak

  DOI：10.1021/ja057592b

  日期：2006.2.1

  Asymmetric syntheses of 4,5,6- and 3,4,5,6-substituted azepanes have been achieved by highly diastereoselective and enantioselective (-)-sparteine-mediated asymmetric lithiation-conjugate additions of N-Boc-N-(p-methoxyphenyl)-2,3-substituted allylamines to a beta-aryl alpha,beta-unsaturated ester followed by hydrolysis, cyclization, and reduction. Access to the enantiomeric adduct is provided by an invertive lithiation-stannylation-lithiation sequence.