p-chlorophenylbuta-1,3-diynyl methyl sulfide | 1392207-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-chlorophenylbuta-1,3-diynyl methyl sulfide
• 英文别名: methylthio (4-(4-chloro)phenyl)butadiyne；1-Chloro-4-(4-methylsulfanylbuta-1,3-diynyl)benzene；1-chloro-4-(4-methylsulfanylbuta-1,3-diynyl)benzene
• CAS: 1392207-19-0
• 化学式: C₁₁H₇ClS
• 分子量: 206.696
• InChiKey: ISDUVSHEKIJFCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  3-(4-氯苯基)-2-丙炔-1-醇 在 manganese(IV) oxide 、 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 5.34h， 生成 p-chlorophenylbuta-1,3-diynyl methyl sulfide
  参考文献：
  名称：

  Efficient One-Pot Preparation of Methylthio Arylbutadiynes by Double Elimination Protocol

  摘要：

  A novel and efficient method for preparation of methylthio arylbutadiynes (Ar-CC-CC-SCH3) was described, and a series of compounds have been expediently obtained by the one-pot protocol starting from methylthiomethyl phenyl sulfone (MP-S) and arylpropargyl aldehydes. The mechanism was discussed on the basis of trapping and characterization of key intermediates. The results from experiments indicated that the reaction involved the initial nucleophilic addition of MP-S to arylpropargyl aldehydes to produce an intermediate carrying two leaving groups and subsequent double elimination reactions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.729280

文献信息

• Transition Metal-Free One-Pot Protocol Toward Conjugated Arylbutadiynyl Sulfides
  作者：Yanqin Zhang、Jing Xiao、Wanrong Dong、Zhihong Peng、Delie An

  DOI：10.1002/hc.21280

  日期：2015.11

  efficient strategy toward conjugated arylbuta-1,3-diynyl sulfides (Ar–C≡C–C≡C–SR) was herein reported. In the newly developed one-pot, three-steps protocol, the synthetically or materially significant arylbuta-1,3-diynyl sulfides were obtained from easily accessible 4-hydrocarbylthio-1-arylbuta-1,3-diones, avoiding usage of expensive terminal aryl acetylenes as substrates or any transition metal complexes

  本文报道了一种针对共轭芳基丁胺-1,3-二炔基硫化物（Ar-C≡C-C≡C-SR）的有效策略。在新开发的一锅三步方案中，从易于获得的 4-hydrocarbylthio-1-arylbuta-1,3-dioones 中获得了具有合成或物质意义的 arylbuta-1,3-diynyl sulfides，避免使用昂贵的终端芳基乙炔作为底物或任何过渡金属配合物作为催化剂。具有可接受产率的有效方法的克级实验提供了工业利益的良好替代方案。
• Efficient One-Pot Preparation of Methylthio Arylbutadiynes by Double Elimination Protocol
  作者：Qiong Su、Hong Yan、Shi-Chao Gao、De-Xun Xie、Qing-Yun Cai、Guang Shao、Zhi-Hong Peng、De-Lie An

  DOI：10.1080/00397911.2012.729280

  日期：2013.10.2

  A novel and efficient method for preparation of methylthio arylbutadiynes (Ar-CC-CC-SCH3) was described, and a series of compounds have been expediently obtained by the one-pot protocol starting from methylthiomethyl phenyl sulfone (MP-S) and arylpropargyl aldehydes. The mechanism was discussed on the basis of trapping and characterization of key intermediates. The results from experiments indicated that the reaction involved the initial nucleophilic addition of MP-S to arylpropargyl aldehydes to produce an intermediate carrying two leaving groups and subsequent double elimination reactions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.