(-)-5-(benzyloxy)-1-(tert-butoxycarbonyl)-3-methyl-2-<(2-propyl)sulfinyl>indole | 141613-08-3

• 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)-3-methyl-2-<(2-propyl)sulfinyl>indole
• 英文别名: (-)-5-(benzyloxy)-1-(tert-butoxycarbonyl)-3-methyl-2-[(2-propyl)sulfinyl]indole；tert-butyl 3-methyl-5-phenylmethoxy-2-[(S)-propan-2-ylsulfinyl]indole-1-carboxylate
• CAS: 141613-08-3
• 化学式: C₂₄H₂₉NO₄S
• 分子量: 427.565
• InChiKey: DHSGSOJGICHBRH-PMERELPUSA-N

物化性质

• 沸点：
  594.0±60.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.53
• 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)-1-(tert-butoxycarbonyl)-3-methyl-2-<(2-propyl)sulfinyl>indole 在 n-butyl tin hydride 、 偶氮二异丁腈 、 copper(l) chloride 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.08h， 生成 (-)-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
• 作为产物：
  描述：

  5-苄氧基吲哚 在 4-二甲氨基吡啶 、 乙基溴化镁 、 仲丁基锂 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.17h， 生成 (-)-5-(benzyloxy)-1-(tert-butoxycarbonyl)-3-methyl-2-<(2-propyl)sulfinyl>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