ethyl 2-{(1S,2R,5S,6S)-2-[(E)-6-iodo-3,3-dimethoxyhepta-1,6-dien-1-yl]-2,6-dimethyl-5-triisopropylsilyloxycyclohexyl}acetate | 1569075-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-{(1S,2R,5S,6S)-2-[(E)-6-iodo-3,3-dimethoxyhepta-1,6-dien-1-yl]-2,6-dimethyl-5-triisopropylsilyloxycyclohexyl}acetate
• CAS: 1569075-99-5
• 化学式: C₃₀H₅₅IO₅Si
• 分子量: 650.754
• InChiKey: FKDFKTNSLRRMKE-XPRKPYFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.83
• 重原子数：
  37.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-{(1S,2R,5S,6S)-2-[(E)-6-iodo-3,3-dimethoxyhepta-1,6-dien-1-yl]-2,6-dimethyl-5-triisopropylsilyloxycyclohexyl}acetate 在 吡啶 、 chromium dichloride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 nickel dichloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 (3S,4S,4aS,12aR,E)-4,12a-dimethyl-7-methylene-3-triisopropylsilyloxy-1,3,4,4a,5,8,9,12a-octahydrobenzo[10]annulene-6,10(2H,7H)-dione
  参考文献：
  名称：

  Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade

  摘要：

  A stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade is described. The substrate, a ten-membered carbocyclic ketone, has been successfully prepared by the Cr-mediated intramolecular alkenylation of the corresponding acyclic compound. The array of functionalities in the product stereoselectively obtained by the cascade reaction is useful for further structural modifications directed toward the total synthesis of fusidane and other triterpenes, and designed molecules intended for studying structure-activity relationships. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.071
• 作为产物：
  描述：

  (1S,2S,3S,4S)-phenyl-2-(2-ethoxy-2-oxoethyl)-1,3-dimethyl-4-(triisopropylsilyloxy)cyclohexanecarboxylate 在 三乙基硅烷 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.42h， 生成 ethyl 2-{(1S,2R,5S,6S)-2-[(E)-6-iodo-3,3-dimethoxyhepta-1,6-dien-1-yl]-2,6-dimethyl-5-triisopropylsilyloxycyclohexyl}acetate
  参考文献：
  名称：

  Stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade

  摘要：

  A stereoselective construction of the ABC-ring system of fusidane triterpenes via intermolecular/transannular Michael reaction cascade is described. The substrate, a ten-membered carbocyclic ketone, has been successfully prepared by the Cr-mediated intramolecular alkenylation of the corresponding acyclic compound. The array of functionalities in the product stereoselectively obtained by the cascade reaction is useful for further structural modifications directed toward the total synthesis of fusidane and other triterpenes, and designed molecules intended for studying structure-activity relationships. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.071