S-Phenyl 2-nonenethioate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-Phenyl 2-nonenethioate
• 英文别名: (E)-S-Phenyl non-2-enethioate；S-phenyl (E)-non-2-enethioate
• 化学式: C₁₅H₂₀OS
• 分子量: 248.389
• InChiKey: POSRFUUJNUCSEX-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-Phenyl 2-nonenethioate 、 辅酶 A 以 四氢呋喃 、 aq. phosphate buffer 为溶剂， 以20%的产率得到(2E)-2-nonenoyl-CoA
  参考文献：
  名称：

  组合化学在抗霉素生物合成中的复用：分子多样性和实用性的扩展

  摘要：

  通过使用多重组合生物合成，完成了抗霉素样化合物库（共380个）的面向多样性的生物合成。核心策略取决于在不同生物合成阶段使用组合化学。该方法适用于聚酮化合物，非核糖体肽以及具有相似生物合成逻辑的杂种的多样化。

  DOI：

  10.1002/anie.201305569
• 作为产物：
  描述：

  乙炔基苯基硫醚 在 polyphosphoric acid trimethylsilyl ester 、 乙基溴化镁 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 1.17h， 生成 S-Phenyl 2-nonenethioate
  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

• Electroinitiated oxygenation of alkenyl sulfides and alkynes in the presence of thiophenol
  作者：Junichi Yoshida、Shogo Nakatani、Sachihiko Isoe

  DOI：10.1021/jo00070a021

  日期：1993.8

  Electrolysis of alkenyl sulfides in the presence of thiophenol with bubbling of molecular oxygen gave the corresponding alpha-(phenylthio) carbonyl compounds with the consumption of a catalytic amount of electricity. An electroinitiated radical chain mechanism has been proposed. The reaction also took place without electrochemical initiation, but much (5-50 times) longer reaction time was required for the completion of the reaction. The potential utility of the present reaction in organic synthesis is demonstrated by the net 1,2-transposition of a phenylthio group and a carbonyl group. The electroinitiated oxygenation of ketene dithioacetals also proceeded smoothly to give the corresponding alpha-(phenylthio) thiol esters. It was also found that the electroinitiated oxygenation of alkynes in the presence of thiophenol gave alpha-(phenylthio) carbonyl compounds. A mechanism involving the initial formation of alkenyl sulfides has been proposed.
• Multiplexing of Combinatorial Chemistry in Antimycin Biosynthesis: Expansion of Molecular Diversity and Utility
  作者：Yan Yan、Jing Chen、Lihan Zhang、Qingfei Zheng、Ying Han、Hua Zhang、Daozhong Zhang、Takayoshi Awakawa、Ikuro Abe、Wen Liu

  DOI：10.1002/anie.201305569

  日期：2013.11.18

  Diversity‐oriented biosynthesis of a library of antimycin‐like compounds (380 altogether) was accomplished by using multiplex combinatorial biosynthesis. The core strategy depends on the use of combinatorial chemistry at different biosynthetic stages. This approach is applicable for the diversification of polyketides, nonribosomal peptides, and the hybrids that share a similar biosynthetic logic.

  通过使用多重组合生物合成，完成了抗霉素样化合物库（共380个）的面向多样性的生物合成。核心策略取决于在不同生物合成阶段使用组合化学。该方法适用于聚酮化合物，非核糖体肽以及具有相似生物合成逻辑的杂种的多样化。
• 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.