(1R,2R,4R,6R)-2-((Z)-2-(dimethyl(phenyl)silyl)-2-(phenylthio)vinyl)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol | 1316735-67-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1R,2R,4R,6R)-2-((Z)-2-(dimethyl(phenyl)silyl)-2-(phenylthio)vinyl)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol
• CAS: 1316735-67-7
• 化学式: C₂₆H₃₂O₂SSi
• 分子量: 436.69
• InChiKey: MUNALXBVWVTKNM-OCNODRIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R,6R)-2-((Z)-2-(dimethyl(phenyl)silyl)-2-(phenylthio)vinyl)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol 在 methyllithium lithium bromide 、 甲基锂 、 间氯过氧苯甲酸 、 sodium bromide 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (1S,2R,6R,7R,8S)-8-(triethylsilyl)-6-methoxy-7-(2-(trimethylsilyl)ethynyl)-8-(phe nylsulfonyl)bicyclo[4.2.0]octan-2-ol
  参考文献：
  名称：

  Synthesis of bicyclo[4.2.0]octan-2-ol, a substructure of solanoeclepin A

  摘要：

  A sesterterpenoid solanoeclepin A (1) has a unique structure including a bicyclo[4.2.0]octane substructure, for which a new synthetic methodology is explored particularly to cyclize functionalized cyclobutane rings. An optically active (R)-carvone and a racemic cyclohexenone were each converted into the respective epoxyvinylsulfones, and then subjected to the heteroatom-directed conjugate addition (HADCA) by a lithium acetylide nucleophile. The intermediate carbanions from HADCA were used for the following epoxide opening reaction yielding the four-membered carbocyclic products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.152
• 作为产物：
  描述：

  (R)-Carvone 在 正丁基锂 、 C₅H₈O*C₆Co₂O₆ 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成 (1R,2R,4R,6R)-2-((Z)-2-(dimethyl(phenyl)silyl)-2-(phenylthio)vinyl)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol
  参考文献：
  名称：

  Synthesis of bicyclo[4.2.0]octan-2-ol, a substructure of solanoeclepin A

  摘要：

  A sesterterpenoid solanoeclepin A (1) has a unique structure including a bicyclo[4.2.0]octane substructure, for which a new synthetic methodology is explored particularly to cyclize functionalized cyclobutane rings. An optically active (R)-carvone and a racemic cyclohexenone were each converted into the respective epoxyvinylsulfones, and then subjected to the heteroatom-directed conjugate addition (HADCA) by a lithium acetylide nucleophile. The intermediate carbanions from HADCA were used for the following epoxide opening reaction yielding the four-membered carbocyclic products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.152