1-[(1R,2S,3S,5S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-2-phenylethanone | 372158-01-5

• 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: 1-[(1R,2S,3S,5S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-2-phenylethanone
• CAS: 372158-01-5
• 化学式: C₂₃H₃₇NO₂Si
• 分子量: 387.638
• InChiKey: NJRLHCOMCWTKIG-XSDIEEQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(1R,2S,3S,5S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-2-phenylethanone 在 swern reagent 、 tetra(tert-butyl)-ammonium fluoride 作用下， 以 四氢呋喃 为溶剂， 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 sodium amide 作用下， 以 乙醚 、 苯 为溶剂， 反应 27.0h， 生成 1-[(1R,2S,3S,5S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-2-phenylethanone
  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.