1-<(Phenylthio)ethynyl>cyclopentene

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-<(Phenylthio)ethynyl>cyclopentene
• 英文别名: 1-(phenylsulfanylethynyl)cyclopentene；2-(Cyclopenten-1-yl)ethynylsulfanylbenzene
• 化学式: C₁₃H₁₂S
• 分子量: 200.304
• InChiKey: QXMZQUJTUDEHDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-<(Phenylthio)ethynyl>-1-cyclopentanol 在 polyphosphoric acid trimethylsilyl ester 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以13%的产率得到S-Phenyl cyclopentylideneethanethioate
  参考文献：
  名称：

  Meyer-Schuster Rearrangement of .gamma.-Sulfur-Substituted Propargyl Alcohols: A Convenient Synthesis of .alpha.,.beta.-Unsaturated Thioesters

  摘要：

  gamma-Sulfur-substituted propargyl alcohols 1a-e and 1ij reacted with polyphosphoric acid trimethylsilyl ester (PPSE) to give the alpha,beta-unsaturated thioesters 3a-e and 3ij in good yields. However, the reactions of 3,3-dibutyl-1 -(phenylthio)propargyl alcohol (1k) and 1-(phenylthio)ethynyl- 1-cyclo alkanols 1l-n with PPSE gave the enyne sulfides 2k-n exclusively.

  DOI：

  10.1021/jo00120a024

文献信息

• Scandium-Catalyzed Carbon−Carbon Bond-Forming Reactions of 3-Sulfanyl- and 3-Selanylpropargyl Alcohols
  作者：Mitsuhiro Yoshimatsu、Tokutaro Otani、Saki Matsuda、Teruhisa Yamamoto、Arisa Sawa

  DOI：10.1021/ol801533p

  日期：2008.10.2

  The scandium-catalyzed substitution reactions of the phenylsulfanyl and phenylselanyl propargyl alcohols 3a-i and 7a-h regioselectively proceeded to give the propargylated compounds 4 and 8 in high yields.
• Meyer-Schuster Rearrangement of .gamma.-Sulfur-Substituted Propargyl Alcohols: A Convenient Synthesis of .alpha.,.beta.-Unsaturated Thioesters
  作者：Mitsuhiro Yoshimatsu、Motoyo Naito、Masataka Kawahigashi、Hiroshi Shimizu、Tadashi Kataoka

  DOI：10.1021/jo00120a024

  日期：1995.7

  gamma-Sulfur-substituted propargyl alcohols 1a-e and 1ij reacted with polyphosphoric acid trimethylsilyl ester (PPSE) to give the alpha,beta-unsaturated thioesters 3a-e and 3ij in good yields. However, the reactions of 3,3-dibutyl-1 -(phenylthio)propargyl alcohol (1k) and 1-(phenylthio)ethynyl- 1-cyclo alkanols 1l-n with PPSE gave the enyne sulfides 2k-n exclusively.