[(1S,2R,4R,6R,7R,8S)-8-(benzenesulfonyl)-6-[dimethyl(phenyl)silyl]oxy-1-methyl-4-prop-1-en-2-yl-7-(2-trimethylsilylethynyl)-2-bicyclo[4.2.0]octanyl] 4-nitrobenzoate | 1298087-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1S,2R,4R,6R,7R,8S)-8-(benzenesulfonyl)-6-[dimethyl(phenyl)silyl]oxy-1-methyl-4-prop-1-en-2-yl-7-(2-trimethylsilylethynyl)-2-bicyclo[4.2.0]octanyl] 4-nitrobenzoate
• CAS: 1298087-11-2
• 化学式: C₃₈H₄₅NO₇SSi₂
• 分子量: 716.015
• InChiKey: ICHCYWYPMHGRIY-JISUFAJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1R,2R,4R,6R)-1-methyl-2-((Z)-2-(dimethyl(phenyl)silyl)-2-(phenylsulfonyl)vinyl)-4-(prop-1-en-2-yl)-7-oxa-bicyclo[4.1.0]heptan-2-ol 在 4-二甲氨基吡啶 、 methyllithium lithium bromide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 [(1S,2R,4R,6R,7R,8S)-8-(benzenesulfonyl)-6-[dimethyl(phenyl)silyl]oxy-1-methyl-4-prop-1-en-2-yl-7-(2-trimethylsilylethynyl)-2-bicyclo[4.2.0]octanyl] 4-nitrobenzoate
  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

文献信息

• Synthesis of bicyclo[4.2.0]octan-2-ol, a substructure of solanoeclepin A
  作者：Minoru Isobe、Supaporn Niyomchon、Chia-Yi Cheng、Anuch Hasakunpaisarn

  DOI：10.1016/j.tetlet.2011.01.152

  日期：2011.4

  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.