Triethyl((1Z)-2-((S)-1-methoxycyclohex-2-enyl)-1-(phenylsulfonyl)vinyl)silane | 1298087-13-4

• 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: Triethyl((1Z)-2-((S)-1-methoxycyclohex-2-enyl)-1-(phenylsulfonyl)vinyl)silane
• 英文别名: [(Z)-1-(benzenesulfonyl)-2-(1-methoxycyclohex-2-en-1-yl)ethenyl]-triethylsilane
• CAS: 1298087-13-4
• 化学式: C₂₁H₃₂O₃SSi
• 分子量: 392.635
• InChiKey: MGVIBUNWNWGXSQ-CZIZESTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Triethyl((1Z)-2-((S)-1-methoxycyclohex-2-enyl)-1-(phenylsulfonyl)vinyl)silane 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 二甲基亚砜 为溶剂， 以58%的产率得到(1R,2S,3R)-2-bromo-3-((Z)-2-(triethylsilyl)-2-(phenylsulfonyl)vinyl)-3-methoxycy clohexanol
  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：

  乙炔基苯基硫醚 在 正丁基锂 、 C₅H₈O*C₆Co₂O₆ 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 Triethyl((1Z)-2-((S)-1-methoxycyclohex-2-enyl)-1-(phenylsulfonyl)vinyl)silane
  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.