(1R,2S,3S,5S)-8-methyl-3-(2-phenylacetyl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid | 372158-04-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (1R,2S,3S,5S)-8-methyl-3-(2-phenylacetyl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid
• CAS: 372158-04-8
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: ZEIVFXUVTJGSQA-NHIYQJMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (1R,2S,3S,5S)-8-methyl-3-(2-phenylacetyl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid 生成 methyl (1R,2S,3S,5S)-8-methyl-3-(2-phenylacetyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
  参考文献：
  名称：

  Synthesis of C-3 alkyl analogs of cocaine

  摘要：

  The first general stereocontrolled approach to C-3 alkyl analogs of cocaine is described. The route utilized versatile intermediates 2 beta -hydroxymethyl-3 alpha -cyanotropane and 2 beta -hydroxymethyl-3 beta -cyanotropane. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01254-0
• 作为产物：
  描述：

  (1R,2S,3R,5S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-methyl-8-azabicyclo[3.2.1]octane-3-carbonitrile 在 swern reagent 、 sodium amide 、 tetra(tert-butyl)-ammonium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 27.0h， 生成 (1R,2S,3S,5S)-8-methyl-3-(2-phenylacetyl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of C-3 alkyl analogs of cocaine

  摘要：

  The first general stereocontrolled approach to C-3 alkyl analogs of cocaine is described. The route utilized versatile intermediates 2 beta -hydroxymethyl-3 alpha -cyanotropane and 2 beta -hydroxymethyl-3 beta -cyanotropane. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01254-0

文献信息

• Synthesis of C-3 alkyl analogs of cocaine
  作者：Shi Xian Deng、Dan Wen Huang、Donald W Landry

  DOI：10.1016/s0040-4039(01)01254-0

  日期：2001.9

  The first general stereocontrolled approach to C-3 alkyl analogs of cocaine is described. The route utilized versatile intermediates 2 beta -hydroxymethyl-3 alpha -cyanotropane and 2 beta -hydroxymethyl-3 beta -cyanotropane. (C) 2001 Elsevier Science Ltd. All rights reserved.