ethyl 2-((1S,2S,5S,6S)-2-((benzylthio)carbonyl)-2,6-dimethyl-5-((triisopropylsilyl)oxy)cyclohexyl)acetate | 1569075-92-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ethyl 2-((1S,2S,5S,6S)-2-((benzylthio)carbonyl)-2,6-dimethyl-5-((triisopropylsilyl)oxy)cyclohexyl)acetate
• CAS: 1569075-92-8
• 化学式: C₂₉H₄₈O₄SSi
• 分子量: 520.849
• InChiKey: XNRWEYFQXNSMLK-LSGWAJPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.01
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  52.6
• 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,2S,5S,6S)-2-((benzylthio)carbonyl)-2,6-dimethyl-5-((triisopropylsilyl)oxy)cyclohexyl)acetate 在 三乙基硅烷 、 palladium diacetate 、 sodium hydride 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 3.25h， 生成 ethyl 2-{(1S,2R,5S,6S)-2-[(E)-6-iodo-3-oxohepta-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
• 作为产物：
  描述：

  在 L-Selectride 、 potassium carbonate 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ethyl 2-((1S,2S,5S,6S)-2-((benzylthio)carbonyl)-2,6-dimethyl-5-((triisopropylsilyl)oxy)cyclohexyl)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

文献信息

• Research on Liebeskind-Srogl coupling/intramolecular Diels-Alder reaction cascade
  作者：Tomohiro Fujii、Yuta Oki、Masahisa Nakada

  DOI：10.1016/j.tetlet.2018.01.046

  日期：2018.3

  The Liebeskind-Srogl coupling/intramolecular Diels-Alder (IMDA) reaction cascade that stereoselectively affords a tricarbocyclic compound with a trans–trans-cis fused ring system including an all-carbon quaternary stereogenic center at the ring junction is described. The cascade reactions proceed quickly and stereoselectively afford the products within 2 h at room temperature in the presence of a suitable

  描述了Liebeskind-Srogl偶联/分子内Diels-Alder（IMDA）反应级联反应，该反应级联选择性地提供了具有反式-反式-顺式稠合环系统的三碳环化合物，该环系统在环结处包括全碳四元立体中心。级联反应进行得很快，并且在合适的硫代酯存在下，在室温下于2小时内立体选择得到产物。所开发的方案以及制备的手性化合物可用于具有反式-反式-顺式稠合环系统的萜类化合物的对映选择性全合成。