5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one | 141613-01-6

• 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: 5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one
• 英文别名: tert-butyl 8b-methyl-2-oxo-7-phenylmethoxy-1,3a-dihydrofuro[2,3-b]indole-4-carboxylate
• CAS: 141613-01-6；141661-45-2
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: MISSYVJDIZELEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one 在 甲酸 、 Raney-nickel W-2 、 硫酸 、 硼烷 、 水 、 sodium 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.1h， 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：

  tert-butyl 1,1-dichloro-8b-methyl-3a-methylsulfanyl-2-oxo-7-phenylmethoxyfuro[2,3-b]indole-4-carboxylate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以84%的产率得到5-(benzyloxy)-8-(tert-butoxycarbonyl)-3a-methyl-3,3a,8,8a-tetrahydro-2H-furo<2,3-b>indol-2-one
  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.