Trifluoro-methanesulfonic acid (1S,3aS,4S,7aR)-1-cyano-3a-hydroxy-7a-methyl-6-methylsulfanyl-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 | 210834-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (1S,3aS,4S,7aR)-1-cyano-3a-hydroxy-7a-methyl-6-methylsulfanyl-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-methylsulfanyl-2,3,4,7-tetrahydro-1H-inden-5-yl] trifluoromethanesulfonate
• CAS: 210834-71-2
• 化学式: C₂₃H₃₀F₃NO₆S₂
• 分子量: 537.622
• InChiKey: LTZMAFDFPZPGHK-QTNNQRCCSA-N

物化性质

• 沸点：
  629.399±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.427±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 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-methylsulfanyl-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20%的产率得到(1R,5R,6S,9S,10R,13R)-9-hydroxy-5-methyl-3-methylsulfanyl-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)-3a-Hydroxy-7a-methyl-4-[(R)-2-(4,6,7,8-tetrahydro-benzo[1,3]dioxin-8a-yl)-ethyl]-5-trimethylsilanyloxy-2,3,3a,6,7,7a-hexahydro-1H-indene-1-carbonitrile 在 四丁基氟化铵 、 silica gel 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 生成 Trifluoro-methanesulfonic acid (1S,3aS,4S,7aR)-1-cyano-3a-hydroxy-7a-methyl-6-methylsulfanyl-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