2-chloro-3-benzylsulfanyl-1-propene | 164529-26-4

• 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: 2-chloro-3-benzylsulfanyl-1-propene
• 英文别名: 2-chloro-3-benzylsulfanylprop-1-ene；2-chloroprop-2-enylsulfanylmethylbenzene
• CAS: 164529-26-4
• 化学式: C₁₀H₁₁ClS
• 分子量: 198.716
• InChiKey: KYKALESKGWFCFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-chloro-3-benzylsulfanyl-1-propene 在 双氧水 、 potassium hydroxide 作用下， 以 水 、 异丙醇 为溶剂， 反应 13.0h， 生成 1-[(propa-1,2-diene-1-sulfonyl)methyl]benzene
  参考文献：
  名称：

  2-氯丙-2-烯-1-基砜的合成，结构与化学转化

  摘要：

  提出了一种绿色方法，用于合成2-氯丙-2-烯-1-基砜，产率为47-94％。通过X射线分析确定2-氯丙-2-烯-1-基苯基砜和2-氯丙-2-烯-1-基甲基砜的分子和晶体结构。在2-氯丙-2-烯-1-基苯基砜的晶体结构中揭示了苯环与双键之间的π-堆积相互作用。发现氯丙烯基砜容易进行脱氯化氢，得到稳定的烯丙基砜，并进行碱水解以产生相应的丙酮基砜。后者可以通过用盐酸羟胺处理而转化为肟。

  DOI：

  10.1134/s1070428019120170
• 作为产物：
  描述：

  二苄基二硫 、 2,3-二氯丙烯 在 一水合肼 、 potassium hydroxide 作用下， 以60%的产率得到2-chloro-3-benzylsulfanyl-1-propene
  参考文献：
  名称：

  Features of the synthesis of unsaturated sulfides proceeding from (2-chloroprop-2-en-1-yl)isothiouronium chloride

  摘要：

  Procedure of synthesis of sulfides containing a chloropropenyl fragment sensitive to bases was modified. The change in the sequence of reagents addition ensuring a contact of isothiouronium salt with a minimal base quantity and the application of a mixture hydrazine hydrate-alkali allowed the preparation of target sulfides under mild conditions in up to 93% yields.

  DOI：

  10.1134/s1070428015020037

文献信息

• Synthesis and structural analysis of 1,1,2-trichloro-2-[2-chloro-2-(organylsulfanyl)ethenyl]cyclopropanes: NMR, X-ray diffraction and QTAIM approach
  作者：Valentina S. Nikonova、Ekaterina P. Levanova、Nikolai A. Korchevin、Igor A. Ushakov、Alexander V. Vashchenko、Igor B. Rozentsveig

  DOI：10.1016/j.molstruc.2017.09.121

  日期：2018.2

  carbenylation of sulfur atom followed by 2,3-sigmatropic rearrangement with subsequent dehydrochloration and cyclopropanation of the terminal double bond. The resulted trichlorocyclopropane derivatives were studied by 1H and 13C NMR spectroscopy as well as X-ray single-crystal analysis that revealed intramolecular CH-π interaction and the formation of intermolecular halogen bonds.

  摘要 通过(2-氯丙-1-烯-3-基)硫化物反应合成了一系列新型1,1,2-三氯-2-[2-氯-2-(有机硫烷基)乙烯基]环丙烷2a-f。与由 CHCl3 生成的二氯卡宾。该过程显然是通过硫原子的羰基化，然后是 2,3-σ 重排以及随后的脱氯化氢和末端双键的环丙烷化来进行的。所得三氯环丙烷衍生物通过 1 H 和 13 C NMR 光谱以及 X 射线单晶分析进行研究，表明分子内 CH-π 相互作用和分子间卤素键的形成。
• Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides
  作者：I. B. Rozentsveig、V. S. Nikonova、E. P. Levanova、N. A. Korchevin

  DOI：10.1134/s1070428016090025

  日期：2016.9

  Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides on heating with solid potassium hydroxide afforded the corresponding 1-(organylsulfanyl)propynes in moderate to high yields and minor isomeric allene derivatives, organylsulfanylpropadienes.
• New approaches to synthesis of unsaturated organochalcogen compounds with two different chalcogen atoms
  作者：E. P. Levanova、V. S. Vakhrina、V. A. Grabel’nykh、I. B. Rozentsveig、N. V. Russavskaya、A. I. Albanov、E. R. Sanzheeva、N. A. Korchevin

  DOI：10.1134/s1070363214110152

  日期：2014.11

  Two approaches to synthesis of bis-chalcogenyl derivatives of propene with two different chalcogen atoms are proposed. Reaction of 2,3-dichloro-1-propene with two different chalcogen nucleophiles PhY- (Y = S, Se) results in a mixture of two products with two identical chalcogen atoms and two products with different ones. The reactivity of PhY- anions under the reaction conditions (60A degrees C) practically does not depend on the Y nature. Reaction of anions RY- (Y = S, Se, Te) with the products of the reaction of 2,3-dichloro-1-propene and organic chalcogenides in the hydrazine hydrate-alkali medium affords the target unsaturated chalcogen-containing compounds with two different chalcogen atoms, 1,2-bis(organylchalcogenyl) propenes in up to 73% yield.
• Specific features of the reactions of 2,3-dichloro-1-propene with dibenzylchalcogenides in the system hydrazine hydrate-alkali
  作者：E. P. Levanova、V. A. Grabel’nykh、V. S. Vakhrina、N. V. Russavskaya、A. I. Albanov、I. B. Rozentsveig、N. A. Korchevin

  DOI：10.1134/s1070363214030050

  日期：2014.3

  Dibenzyldisulfide and -diselenide react with 2,3-dichloro-1-propene in the system hydrazine hydrate-KOH by the domino mechanism: nucleophilic substitution of the allyl chlorine, dehydrochlorination with participation of the chlorine atom at the sp (2)-carbon atom, allene-acetylene rearrangement, nucleophilic addition of the chalcogenide reagent to the triple bond. The effect of the nature of the chalcogen atom and the benzyl substituent on the studied domino reaction is discussed.