tert-butyl N-[(3S)-2-sulfanylideneazepan-3-yl]carbamate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: tert-butyl N-[(3S)-2-sulfanylideneazepan-3-yl]carbamate
• 化学式: C₁₁H₂₀N₂O₂S
• 分子量: 244.358
• InChiKey: BCMGPGBFUAFKGM-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(3S)-2-sulfanylideneazepan-3-yl]carbamate 在 盐酸羟胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 以53%的产率得到tert-butyl N-[(6S)-7-(hydroxyamino)-3,4,5,6-tetrahydro-2H-azepin-6-yl]carbamate
  参考文献：
  名称：

  Synthesis of a hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative useful as an HIV integrase inhibitor

  摘要：

  The hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative 1 could be obtained by three synthetic strategies, which allowed access to multigram amounts of material of high purity and ee. Two strategies involved alternative approaches to the bicyclic pyrimidone core, with the most efficient one being a two-step sequence from commercially available starting materials exploiting a little precedented cyclisation reaction. The remaining steps to 1 included an efficient crystallisation of an intermediate as a single stereoisomer. An alternative strategy employing a chiral starting material led to products of low optical purity but allowed the assignment of the configuration of the stereogenic centre of 1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.072
• 作为产物：
  描述：

  L-(-)-3-N-Boc-氨基-2-氮杂丙酮 在 tetraphosphorus decasulfide 、 六甲基二硅氧烷 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到tert-butyl N-[(3S)-2-sulfanylideneazepan-3-yl]carbamate
  参考文献：
  名称：

  Synthesis of a hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative useful as an HIV integrase inhibitor

  摘要：

  The hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative 1 could be obtained by three synthetic strategies, which allowed access to multigram amounts of material of high purity and ee. Two strategies involved alternative approaches to the bicyclic pyrimidone core, with the most efficient one being a two-step sequence from commercially available starting materials exploiting a little precedented cyclisation reaction. The remaining steps to 1 included an efficient crystallisation of an intermediate as a single stereoisomer. An alternative strategy employing a chiral starting material led to products of low optical purity but allowed the assignment of the configuration of the stereogenic centre of 1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.072

文献信息

• Synthesis of a hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative useful as an HIV integrase inhibitor
  作者：Marco Ferrara、Benedetta Crescenzi、Monica Donghi、Ester Muraglia、Emanuela Nizi、Silvia Pesci、Vincenzo Summa、Cristina Gardelli

  DOI：10.1016/j.tetlet.2007.09.072

  日期：2007.11

  The hexahydropyrimido[1,2-a]azepine-2-carboxamide derivative 1 could be obtained by three synthetic strategies, which allowed access to multigram amounts of material of high purity and ee. Two strategies involved alternative approaches to the bicyclic pyrimidone core, with the most efficient one being a two-step sequence from commercially available starting materials exploiting a little precedented cyclisation reaction. The remaining steps to 1 included an efficient crystallisation of an intermediate as a single stereoisomer. An alternative strategy employing a chiral starting material led to products of low optical purity but allowed the assignment of the configuration of the stereogenic centre of 1. (c) 2007 Elsevier Ltd. All rights reserved.