ethyl 2-(3'-phenylsulfanylpropyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 2-(3'-phenylsulfanylpropyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate
• 英文别名: ethyl (1S,2S,4S)-2-(3-phenylsulfanylpropyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate
• 化学式: C₁₉H₂₄O₂S
• 分子量: 316.464
• InChiKey: AEZBUVYPQURULL-FCEWJHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3'-phenylsulfanylpropyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 以98%的产率得到ethyl 2-(3'-phenylsulfinylpropyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate
  参考文献：
  名称：

  Intramolecular acylation of α-sulfinyl carbanions with masked α,β-unsaturated esters: a general strategy to 5-alkylidene-2-cyclopentenones

  摘要：

  A general method for the preparation of 5-alkylidene-2-cyclopentenones and their 2-phenylsulfanyl substituted derivatives, involving the intramolecular acylation of cc-sulfinyl carbanions with cyclopentadiene-alpha,beta-unsaturated esters as the key reaction followed by flash vacuum pyrolysis, is described. The reactions start from readily available Diels-Alder adducts, synthons of alpha-carbanions of alpha,beta-unsaturated esters. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.036
• 作为产物：
  描述：

  [(3-溴丙基)硫基]苯 、 endo-ethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate 在 lithium diisopropyl amide 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以68%的产率得到ethyl 2-(3'-phenylsulfanylpropyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate
  参考文献：
  名称：

  Intramolecular acylation of α-sulfinyl carbanions with masked α,β-unsaturated esters: a general strategy to 5-alkylidene-2-cyclopentenones

  摘要：

  A general method for the preparation of 5-alkylidene-2-cyclopentenones and their 2-phenylsulfanyl substituted derivatives, involving the intramolecular acylation of cc-sulfinyl carbanions with cyclopentadiene-alpha,beta-unsaturated esters as the key reaction followed by flash vacuum pyrolysis, is described. The reactions start from readily available Diels-Alder adducts, synthons of alpha-carbanions of alpha,beta-unsaturated esters. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.036

文献信息

• Intramolecular acylation of α-sulfinyl carbanions with masked α,β-unsaturated esters: a general strategy to 5-alkylidene-2-cyclopentenones
  作者：Manat Pohmakotr、Sirinporn Thamapipol、Patoomratana Tuchinda、Vichai Reutrakul

  DOI：10.1016/j.tet.2006.12.036

  日期：2007.2

  A general method for the preparation of 5-alkylidene-2-cyclopentenones and their 2-phenylsulfanyl substituted derivatives, involving the intramolecular acylation of cc-sulfinyl carbanions with cyclopentadiene-alpha,beta-unsaturated esters as the key reaction followed by flash vacuum pyrolysis, is described. The reactions start from readily available Diels-Alder adducts, synthons of alpha-carbanions of alpha,beta-unsaturated esters. (c) 2006 Elsevier Ltd. All rights reserved.