5-(Ethylthio)-1-pentyne | 57079-99-9

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 5-(Ethylthio)-1-pentyne
• 英文别名: 5-ethylsulfanyl-pent-1-yne；5-Ethylsulfanylpent-1-yne
• CAS: 57079-99-9
• 化学式: C₇H₁₂S
• 分子量: 128.238
• InChiKey: KPIKWDRHHHHJIF-UHFFFAOYSA-N

物化性质

• 沸点：
  176.2±23.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(Ethylthio)-1-pentyne 在 trans-bis(triphenylphosphine)palladium(II) chloride copper(l) iodide 、 potassium trimethylsilonate 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 32.0h， 生成 2-Diazo-1-<2-(5-(ethylthio)pent-1-ynyl)phenyl>propan-1-one
  参考文献：
  名称：

  A Tandem Cyclization-Onium Ylide Rearrangement-Cycloaddition Sequence for the Synthesis of Benzo-Substituted Cyclopentenones

  摘要：

  A new annulation sequence leading to benzo-substituted cyclopentenones is effected by treating o-alkynyl-substituted alpha-diazoacetophenones containing tethered heteroatoms with Rh(II) carboxylates. The reaction involves addition of the initially formed keto carbenoid onto the acetylenic pi-bond to give a rearranged vinyl carbenoid. Sulfonium ylide formation occurred both intra- and intermolecularly when the reaction was carried out in the presence of a sulfide. In the case where an ether oxygen was present on the backbone of the vinyl carbenoid, the resulting oxonium ylide underwent a [1,2]- or [2,3]-shift to give the rearranged product. These cyclic metallocarbenoids were also found to interact with a neighboring carbonyl or oximino pi-bond to produce carbonyl or azomethine ylides. The 1,3-dipoles generated in this manner were trapped with dimethyl acetylenedicarboxylate. The domino transformation was also performed intramolecularly by attaching a trapping agent directly to the carbonyl group. Incorporation of an amido carbonyl on the alkyne side chain was found to dramatically alter the course of the tandem annulation reaction. A novel rearranged cycloadduct was formed in high yield whose structure was elucidated by X-ray crystallography. The mechanism for its formation involves the opening of a transient intermediate oxabicyclo[2.2.1]heptane followed by a Wagner-Meerwein rearrangement.

  DOI：

  10.1021/jo00106a014
• 作为产物：
  描述：

  戊-4-炔基对甲苯磺酸酯 在 lithium bromide 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 5-(Ethylthio)-1-pentyne
  参考文献：
  名称：

  Organocuivreux黑胶唱片：IV。阿尔西地区烷基锡的区域选拔等课程

  摘要：

  烷基铜化合物向各种炔烃HCC（CH 2）2 Z（n = 2，3，Z = X，NEt 2，SEt，OR）的顺式加成显示区域选择性取决于各种因素，主要因素是功能的性质和溶剂。由此获得的乙烯基铜衍生物已被羧化，碘化和烷基化。

  DOI：

  10.1016/s0022-328x(00)91950-8

文献信息

• A Tandem Cyclization-Onium Ylide Rearrangement-Cycloaddition Sequence for the Synthesis of Benzo-Substituted Cyclopentenones
  作者：Albert Padwa、Jamal M. Kassir、Mark A. Semones、M. David Weingarten

  DOI：10.1021/jo00106a014

  日期：1995.1

  A new annulation sequence leading to benzo-substituted cyclopentenones is effected by treating o-alkynyl-substituted alpha-diazoacetophenones containing tethered heteroatoms with Rh(II) carboxylates. The reaction involves addition of the initially formed keto carbenoid onto the acetylenic pi-bond to give a rearranged vinyl carbenoid. Sulfonium ylide formation occurred both intra- and intermolecularly when the reaction was carried out in the presence of a sulfide. In the case where an ether oxygen was present on the backbone of the vinyl carbenoid, the resulting oxonium ylide underwent a [1,2]- or [2,3]-shift to give the rearranged product. These cyclic metallocarbenoids were also found to interact with a neighboring carbonyl or oximino pi-bond to produce carbonyl or azomethine ylides. The 1,3-dipoles generated in this manner were trapped with dimethyl acetylenedicarboxylate. The domino transformation was also performed intramolecularly by attaching a trapping agent directly to the carbonyl group. Incorporation of an amido carbonyl on the alkyne side chain was found to dramatically alter the course of the tandem annulation reaction. A novel rearranged cycloadduct was formed in high yield whose structure was elucidated by X-ray crystallography. The mechanism for its formation involves the opening of a transient intermediate oxabicyclo[2.2.1]heptane followed by a Wagner-Meerwein rearrangement.
• Organocuivreux vinyliques
  作者：A. Alexakis、J. Normant、J. Villieras

  DOI：10.1016/s0022-328x(00)91950-8

  日期：1975.9

  The syn addition of alkylcopper compounds to various alkynes HCC(CH2)2Z (n = 2, 3, Z = X, NEt2, SEt, OR) shows a regio-selectivity dependant on various factors, the major factors being the nature of the function and the solvent. The vinylcopper derivatives thus obtained have been carboxylated, iodinated and alkylated.

  烷基铜化合物向各种炔烃HCC（CH 2）2 Z（n = 2，3，Z = X，NEt 2，SEt，OR）的顺式加成显示区域选择性取决于各种因素，主要因素是功能的性质和溶剂。由此获得的乙烯基铜衍生物已被羧化，碘化和烷基化。