5-(benzyloxy)-1-(tert-butoxycarbonyl)-2-hydroxy-3-methyl-3-<2-oxo-2-(methylamino)ethyl>indole | 141613-18-5

• 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)-1-(tert-butoxycarbonyl)-2-hydroxy-3-methyl-3-<2-oxo-2-(methylamino)ethyl>indole
• 英文别名: tert-butyl 2-hydroxy-3-methyl-3-[2-(methylamino)-2-oxoethyl]-5-phenylmethoxy-2H-indole-1-carboxylate
• CAS: 141613-18-5；141634-74-4
• 化学式: C₂₄H₃₀N₂O₅
• 分子量: 426.513
• InChiKey: JIRSXAMVTSRTPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  88.1
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-1-(tert-butoxycarbonyl)-2-hydroxy-3-methyl-3-<2-oxo-2-(methylamino)ethyl>indole 在 四溴化碳 、 三苯基膦 作用下， 以 乙醚 为溶剂， 反应 4.25h， 以50%的产率得到5-(benzyloxy)-8-(tert-butoxycarbonyl)-1,3a-dimethyl-3,3a,8,8a-tetrahydropyrrolo<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
• 作为产物：
  描述：

  5-(benzyloxy)-1-(tert-butoxycarbonyl)-3-methylindole 在 偶氮二异丁腈 、 仲丁基锂 、 三正丁基氢锡 、 间氯过氧苯甲酸 、 copper(l) chloride 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.75h， 生成 5-(benzyloxy)-1-(tert-butoxycarbonyl)-2-hydroxy-3-methyl-3-<2-oxo-2-(methylamino)ethyl>indole
  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.