O-benzyleseroline | 141613-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: O-benzyleseroline
• 英文别名: Eseroline, benzyl ether；3,4,8b-trimethyl-7-phenylmethoxy-2,3a-dihydro-1H-pyrrolo[2,3-b]indole
• CAS: 141613-05-0；141723-96-8
• 化学式: C₂₀H₂₄N₂O
• 分子量: 308.423
• InChiKey: YWUKCFCWYJCPBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-benzyleseroline 在 Raney-nickel W-2 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.1h， 生成 毒扁豆碱
  参考文献：
  名称：

  The enantioselective synthesis of (-)-physostigmine via chiral sulfoxides

  摘要：

  The total synthesis of naturally occurring (-)-physostigmine is described. The key element for the asymmetric induction is the chirality transfer from optically active 2-(alkylsulfinyl)indoles to indoline butyrolactones bearing two chiral centers. Novel features of this synthesis involve the use of a new class of sulfoxylating agents, N-(alkylsulfinyl)oxazolidinones, to prepare the starting indolyl sulfoxides and the correlation of the size of the alkyl group on the sulfoxide with the degree of asymmetric induction. The overall synthesis requires a dozen steps from commercially available 5-(benzyloxy)indole.

  DOI：

  10.1021/ja00040a013
• 作为产物：
  描述：

  3-甲基-5-苯甲氧基-1H-吲哚 在 4-二甲氨基吡啶 、 甲酸 、 偶氮二异丁腈 、 硫酸 、 硼烷 、 水 、 仲丁基锂 、 三正丁基氢锡 、 三乙胺 、 间氯过氧苯甲酸 、 copper(l) chloride 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.75h， 生成 O-benzyleseroline
  参考文献：
  名称：

  The enantioselective synthesis of (-)-physostigmine via chiral sulfoxides

  摘要：

  The total synthesis of naturally occurring (-)-physostigmine is described. The key element for the asymmetric induction is the chirality transfer from optically active 2-(alkylsulfinyl)indoles to indoline butyrolactones bearing two chiral centers. Novel features of this synthesis involve the use of a new class of sulfoxylating agents, N-(alkylsulfinyl)oxazolidinones, to prepare the starting indolyl sulfoxides and the correlation of the size of the alkyl group on the sulfoxide with the degree of asymmetric induction. The overall synthesis requires a dozen steps from commercially available 5-(benzyloxy)indole.

  DOI：

  10.1021/ja00040a013

文献信息

• The enantioselective synthesis of (-)-physostigmine via chiral sulfoxides
  作者：J. P. Marino、S. Bogdan、K. Kimura

  DOI：10.1021/ja00040a013

  日期：1992.7

  The total synthesis of naturally occurring (-)-physostigmine is described. The key element for the asymmetric induction is the chirality transfer from optically active 2-(alkylsulfinyl)indoles to indoline butyrolactones bearing two chiral centers. Novel features of this synthesis involve the use of a new class of sulfoxylating agents, N-(alkylsulfinyl)oxazolidinones, to prepare the starting indolyl sulfoxides and the correlation of the size of the alkyl group on the sulfoxide with the degree of asymmetric induction. The overall synthesis requires a dozen steps from commercially available 5-(benzyloxy)indole.