Trifluoro-methanesulfonic acid (1S,3aS,4S,7aR)-1-cyano-3a-hydroxy-7a-methyl-6-phenylsulfanyl-4-[(R)-2-(4,6,7,8-tetrahydro-benzo[1,3]dioxin-8a-yl)-ethyl]-2,3,3a,4,7,7a-hexahydro-1H-inden-5-yl ester | 210834-68-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Trifluoro-methanesulfonic acid (1S,3aS,4S,7aR)-1-cyano-3a-hydroxy-7a-methyl-6-phenylsulfanyl-4-[(R)-2-(4,6,7,8-tetrahydro-benzo[1,3]dioxin-8a-yl)-ethyl]-2,3,3a,4,7,7a-hexahydro-1H-inden-5-yl ester
• 英文别名: [(1S,3aS,4S,7aR)-4-[2-[(8aR)-4,6,7,8-tetrahydro-1,3-benzodioxin-8a-yl]ethyl]-1-cyano-3a-hydroxy-7a-methyl-6-phenylsulfanyl-2,3,4,7-tetrahydro-1H-inden-5-yl] trifluoromethanesulfonate
• CAS: 210834-68-7
• 化学式: C₂₈H₃₂F₃NO₆S₂
• 分子量: 599.692
• InChiKey: IXZNIOAOUVLBAN-LYOOBKATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (1S,3aS,4S,7aR)-1-cyano-3a-hydroxy-7a-methyl-6-phenylsulfanyl-4-[(R)-2-(4,6,7,8-tetrahydro-benzo[1,3]dioxin-8a-yl)-ethyl]-2,3,3a,4,7,7a-hexahydro-1H-inden-5-yl ester 在 Pd(dppb) potassium acetate 、 2,4-滴二甲胺盐 作用下， 以70%的产率得到(1R,5R,6S,9S,10R,13R)-9-hydroxy-5-methyl-3-phenylsulfanyl-14,16-dioxapentacyclo[11.4.4.01,13.02,10.05,9]henicosa-2,18-diene-6-carbonitrile
  参考文献：
  名称：

  Intramolecular Heck cyclization of α-sulfenyl enol triflates. Asymmetric synthesis of a pentacyclic cardenolide precursor having functionality at C-11

  摘要：

  A concise route to the core of complex cardenolides is described. The sequence features use of a sulfone to join enantioenriched A and D ring fragments and also control intramolecular aldolization to generate ring C and an intramolecular Heck cyclization of an alpha-sulfenyl enol triflate to form the steroid skeleton. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00860-0
• 作为产物：
  描述：

  (1S,3aR,7aR)-7a-Methyl-4-[(R)-2-(4,6,7,8-tetrahydro-benzo[1,3]dioxin-8a-yl)-ethyl]-3a,5-bis-trimethylsilanyloxy-2,3,3a,6,7,7a-hexahydro-1H-indene-1-carbonitrile 在 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 生成 Trifluoro-methanesulfonic acid (1S,3aS,4S,7aR)-1-cyano-3a-hydroxy-7a-methyl-6-phenylsulfanyl-4-[(R)-2-(4,6,7,8-tetrahydro-benzo[1,3]dioxin-8a-yl)-ethyl]-2,3,3a,4,7,7a-hexahydro-1H-inden-5-yl ester
  参考文献：
  名称：

  Intramolecular Heck cyclization of α-sulfenyl enol triflates. Asymmetric synthesis of a pentacyclic cardenolide precursor having functionality at C-11

  摘要：

  A concise route to the core of complex cardenolides is described. The sequence features use of a sulfone to join enantioenriched A and D ring fragments and also control intramolecular aldolization to generate ring C and an intramolecular Heck cyclization of an alpha-sulfenyl enol triflate to form the steroid skeleton. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00860-0