Pseudococaine hydrochloride | 6363-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Pseudococaine hydrochloride
• 英文别名: methyl (1R,2S,3S,5S)-3-benzoyloxy-N(8)-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride；(+)-pseudococaine hydrochloride；pseudococaine hydrochloride；(+)-pseudococaine; hydrochloride；(+)-Pseudococain; Hydrochlorid；methyl (1R,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate;hydrochloride
• CAS: 6363-57-1
• 化学式: C₁₇H₂₁NO₄*ClH
• 分子量: 339.819
• InChiKey: PIQVDUKEQYOJNR-UOIZBMALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl (1R,2S,3R,4R,5S)-3-hydroxy-4-iodo-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 在 盐酸 、 4-二甲氨基吡啶 、 氯化亚砜 、 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 26.08h， 生成 Pseudococaine hydrochloride
  参考文献：
  名称：

  Asymmetric Synthesis of the Tropane Alkaloid (+)-Pseudococaine via Ring-Closing Iodoamination

  摘要：

  Ring-closing iodoamination of terf-butyl 2-hydroxy-7[N-methyl-N-(alpha-methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane scaffolds in >99:1 dr. Subsequent elaboration of one of these templates provided access to (+)-pseudococaine hydrochloride, in seven steps and 31% overall yield from commercially available starting materials.

  DOI：

  10.1021/ol3020607

文献信息

• PREPARATION OF (-)-COCAINE HYDROCHLORIDE
  申请人：Cody Laboratories, Inc.

  公开号：US20190224184A1

  公开（公告）日：2019-07-25

  Efficient methods are provided for large scale production of ethyl cocaine-free cocaine hydrochloride. Compositions and methods comprising administration of cocaine hydrochloride are provided.
• Asymmetric Synthesis of the Tropane Alkaloid (+)-Pseudococaine via Ring-Closing Iodoamination
  作者：E. Anne Brock、Stephen G. Davies、James A. Lee、Paul M. Roberts、James E. Thomson

  DOI：10.1021/ol3020607

  日期：2012.8.17

  Ring-closing iodoamination of terf-butyl 2-hydroxy-7[N-methyl-N-(alpha-methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-alpha-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane scaffolds in >99:1 dr. Subsequent elaboration of one of these templates provided access to (+)-pseudococaine hydrochloride, in seven steps and 31% overall yield from commercially available starting materials.