(1R,5S)-3-[2-(2-Bromo-ethyl)-phenyl]-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl ester | 275823-07-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1R,5S)-3-[2-(2-Bromo-ethyl)-phenyl]-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl ester
• 英文别名: methyl (1R,5S)-3-[2-(2-bromoethyl)phenyl]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
• CAS: 275823-07-9
• 化学式: C₁₈H₂₂BrNO₂
• 分子量: 364.282
• InChiKey: HXZCCONRVHYRQE-XJKSGUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (1R,5S)-3-[2-(2-Bromo-ethyl)-phenyl]-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 methyl (1'R,2'R,3S,5'S)-8'-methylspiro[1,2-dihydroindene-3,3'-8-azabicyclo[3.2.1]octane]-2'-carboxylate 、 methyl (1'R,2'R,3R,5'S)-8'-methylspiro[1,2-dihydroindene-3,3'-8-azabicyclo[3.2.1]octane]-2'-carboxylate
  参考文献：
  名称：

  Synthesis of novel spirocyclic cocaine analogs using the Suzuki coupling

  摘要：

  Novel spirocyclic cocaine analogs were synthesized by employing the Suzuki coupling of ortho-substituted arylboronic acids and an enol triflate derived from cocaine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00113-1
• 作为产物：
  描述：

  (1R)-2-carboxymethoxy-3-[[(trifluoromethyl)sulfonyl]oxy]-8-methyl-8-azabicyclo[3.2.1]oct-2-ene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四溴化碳 、 四丁基氟化铵 、 sodium carbonate 、 三苯基膦 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (1R,5S)-3-[2-(2-Bromo-ethyl)-phenyl]-8-methyl-8-aza-bicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of novel spirocyclic cocaine analogs using the Suzuki coupling

  摘要：

  Novel spirocyclic cocaine analogs were synthesized by employing the Suzuki coupling of ortho-substituted arylboronic acids and an enol triflate derived from cocaine. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00113-1

文献信息

• Synthesis of novel spirocyclic cocaine analogs using the Suzuki coupling
  作者：Sukumar Sakamuri、Clifford George、Judith Flippen-Anderson、Alan P Kozikowski

  DOI：10.1016/s0040-4039(00)00113-1

  日期：2000.3

  Novel spirocyclic cocaine analogs were synthesized by employing the Suzuki coupling of ortho-substituted arylboronic acids and an enol triflate derived from cocaine. (C) 2000 Elsevier Science Ltd. All rights reserved.