(Z)-7-Phenylsulfanyl-hept-2-enoic acid ethyl ester | 125115-33-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-7-Phenylsulfanyl-hept-2-enoic acid ethyl ester
• CAS: 125115-33-5
• 化学式: C₁₅H₂₀O₂S
• 分子量: 264.389
• InChiKey: AZXSNSWGZWCIPO-WQLSENKSSA-N

物化性质

• 沸点：
  379.4±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-7-Phenylsulfanyl-hept-2-enoic acid ethyl ester 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 为溶剂， 反应 15.0h， 以98%的产率得到ethyl cis-7-chloro-7-phenylthio-2-heptenoate
  参考文献：
  名称：

  Generation and intramolecular cyclization of α-phenylsulfenyl and α-alkylsulfenyl radicals

  摘要：

  alpha-Phenylsulfenyl radicals are generated by the reaction of diphenyl dithioacetals or phenyl alpha-chlorosulfides with tributyltin hydride. Alkyl phenyl dithioacetals react selectively with tributyltin hydride to give alpha-alkylsulfenyl radicals. 5-Exo-type of intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The cis/trans ratio of the cyclized product varies according to the reaction rates. With a faster cyclization, cis-isomer is the major product. A slower cyclization gives more trans-product. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00156-7
• 作为产物：
  描述：

  tetrahydro-2H-2-pyranol 在 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (Z)-7-Phenylsulfanyl-hept-2-enoic acid ethyl ester
  参考文献：
  名称：

  Generation and intramolecular cyclization of α-phenylsulfenyl and α-alkylsulfenyl radicals

  摘要：

  alpha-Phenylsulfenyl radicals are generated by the reaction of diphenyl dithioacetals or phenyl alpha-chlorosulfides with tributyltin hydride. Alkyl phenyl dithioacetals react selectively with tributyltin hydride to give alpha-alkylsulfenyl radicals. 5-Exo-type of intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The cis/trans ratio of the cyclized product varies according to the reaction rates. With a faster cyclization, cis-isomer is the major product. A slower cyclization gives more trans-product. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00156-7

文献信息

• Generation and intramolecular cyclization of α-sulfinyl and α-sulfonyl radicals
  作者：Bor-Wen Ke、Chao-Hsiung Lin、Yeun-Min Tsai

  DOI：10.1016/s0040-4020(97)00472-9

  日期：1997.6

  alpha-Phenylsulfinyl and alpha-Phenylsulfonyl radicals are generated by the reactions of alpha-chlorosulfoxides and alpha-chlorosulfones with tributyltin hydride, respectively. High reaction concentration (0.2 M) is required to ensure efficient generations of these radicals. The 5-exo-type intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The sulfinyl group only induces mild diastereoselectivity on the cyclization. (C) 1997 Elsevier Science Ltd.