3-n-Butyl-1-(phenylthio)hept-1-yn-3-ol

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-n-Butyl-1-(phenylthio)hept-1-yn-3-ol
• 英文别名: 5-(2-Phenylsulfanylethynyl)nonan-5-ol
• 化学式: C₁₇H₂₄OS
• 分子量: 276.443
• InChiKey: FRSDOQIOVVQASM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-n-Butyl-1-(phenylthio)hept-1-yn-3-ol 在 polyphosphoric acid trimethylsilyl ester 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以70%的产率得到(Z)-3-n-Butyl-1-(phenylthio)hept-3-ene-1-yne
  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
• 作为产物：
  描述：

  5-壬酮 、 乙炔基苯基硫醚 在 乙基溴化镁 作用下， 以 乙醚 为溶剂， 以73%的产率得到3-n-Butyl-1-(phenylthio)hept-1-yn-3-ol
  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

• 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.