1-苯基-2-苯基硫代乙烯 | 16619-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯基-2-苯基硫代乙烯
• 英文名称: 1-phenyl-2-phenylthioethene
• 英文别名: phenyl(styryl)sulfane；Phenyl styryl sulfide；2-phenylethenylsulfanylbenzene
• CAS: 16619-61-7
• 化学式: C₁₄H₁₂S
• 分子量: 212.315
• InChiKey: NCSYOCXYJXZCGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-苯基-2-苯基硫代乙烯 生成 1-phenyl-2-phenylsulfanyl-ethanol
  参考文献：
  名称：

  Transfer Reactions Involving Boron. III. Hydroboration Studies with Enethiol Ethers

  摘要：

  DOI：

  10.1021/ja00897a018
• 作为产物：
  描述：

  O-<2,2-bis(phenylthio)-1-phenylethyl> S-methyl dithiocarbonate 在 三乙基硼 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.25h， 以70%的产率得到1-苯基-2-苯基硫代乙烯
  参考文献：
  名称：

  Facile reduction of dithiocarbonates with n-Bu3SnH-Et3B. Easy access to hydrocarbons from secondary alcohols

  摘要：

  DOI：

  10.1016/s0040-4039(00)82283-2

文献信息

• Synthesis of Sulfoxides by the Hydrogen Peroxide Induced Oxidation of Sulfides Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin:  Scope and Chemoselectivity
  作者：Enrico Baciocchi、Maria Francesca Gerini、Andrea Lapi

  DOI：10.1021/jo049879h

  日期：2004.5.1

  The oxidation of sulfides with H2O2 catalyzed by iron tetrakis(pentafluorophenyl)porphyrin in EtOH is an efficient and chemoselective process. With a catalyst concentration 0.03−0.09% of that of the substrate, sulfoxides are obtained with yields generally around 90−95% of isolated product. With vinyl and allyl sulfides, no epoxidation is observed. With a catalyst concentration between 0.09% and 0.25%

  四（五氟苯基）卟啉铁在EtOH中催化的H 2 O 2氧化硫化物是一种有效的化学选择过程。在催化剂浓度为底物浓度的0.03-0.09％的情况下，获得的亚砜的收率通常约为分离产物的90-95％。对于乙烯基和烯丙基硫化物，未观察到环氧化。催化剂浓度为底物浓度的0.09％至0.25％，可以以几乎定量的产率获得砜，并且在亚砜的合成中观察到相同的高化学选择性。
• Reactions of Sulfoxides with Magnesium Amides. Transformation of Sulfoxides into Sulfides, Dithioacetals, and Vinyl Sulfides
  作者：Kazuhiro Kobayashi、Masataka Kawakita、Kouichi Yokota、Tohru Mannami、Koji Yamamoto、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1246/bcsj.68.1401

  日期：1995.5

  ethylmagnesium bromide and secondary amines, such as diisopropylamine (DIPA) or 2,2,6,6-tetramethylpiperidine (TMP) in diethyl ether, were examined. Diaryl sulfoxides were heated with the diisopropylaminomagnesium reagent in diethyl ether to give the corresponding diaryl sulfides in 42—52% yields. Sulfoxides bearing hydrogens at the α-positon only (RSOCH2R1) reacted with the tetramethylpiperidinomagnesium

  研究了亚砜与由溴化乙基镁和仲胺（例如二异丙胺 (DIPA) 或 2,2,6,6-四甲基哌啶 (TMP) 在乙醚中的反应）原位生成的氨基镁的反应。二芳基亚砜与二异丙基氨基镁试剂在乙醚中一起加热，得到相应的二芳基硫化物，产率为 42-52%。仅在 α 位带有氢的亚砜 (RSOCH2R1) 在室温下与四甲基哌啶镁试剂反应，生成相应的二硫缩醛 (RSCHR1SR)，产率为 47-86%。在室温下用氨基镁处理在 α 位和 β 位都带有氢的亚砜 (RSOCHR1CHR2R3) 得到相应的乙烯基硫化物 (RSCR1=CR2R3)，产率为 52-72%，伴随着 2。3-27% 的相应二硫代缩醛的产率。讨论了导致形成硫稳定碳正离子中间体的产物的途径。
• Electrochemical Properties and Fluorination of Cyclopropane Derivatives Bearing Arylthio Groups
  作者：Sayaka Oyanagi、Hideki Ishii、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.1149/1945-7111/abb83b

  日期：2020.1.12

  Electrochemical analyses of phenylthiocyclopropane derivatives and bis(arylthio)cyclopropanes were comparatively studied by cyclic voltammetric measurements. Based on the substituent effects on their oxidation potentials, a cyclopropane ring was confirmed to have a double bond system as reported. Anodic fluorination of phenylthiocyclopropanes resulted in the formation of sulfoxide and/or ring opening

  通过循环伏安法比较研究了苯硫基环丙烷衍生物和双（芳硫基）环丙烷的电化学分析。基于取代基对其氧化电势的影响，已证实环丙烷环具有双键系统。苯硫基环丙烷的阳极氟化导致形成亚砜和/或开环氟化产物，而1,1-双（芳硫基）环丙烷主要提供脱硫的单氟化环丙烷和亚砜以及开环氟化产物。这是环丙烷环的首次成功的电化学氟化。
• Hydrothiolation of Unactivated Alkynes Catalyzed by Indium(III) Bromide
  作者：J. S. Yadav、B. V. Subba Reddy、A. Raju、K. Ravindar、Gakul Baishya

  DOI：10.1246/cl.2007.1474

  日期：2007.12.5

  Indium(III) bromide is found to catalyze efficiently the hydrothiolation of unactivated alkynes with various thiols under mild conditions to produce the corresponding dithioacetals in excellent yields. However, addition of aromatic thiols on aromatic alkynes gave the β-vinyl sulfides in high yields. This new procedure offers significant advantages such as high conversions, short reaction times, and

  发现溴化铟 (III) 在温和条件下有效催化未活化炔烃与各种硫醇的氢硫醇化反应，以优异的产率生产相应的二硫代缩醛。然而，在芳香炔烃上加入芳香硫醇以高产率得到 β-乙烯基硫化物。这种新方法具有显着的优势，例如转化率高、反应时间短和操作简单。
• Stereo-recognizing transformation of (E)-alkenyl halides into sulfides catalyzed by nickel(0) triethyl phosphite complex
  作者：Yasutaka Yatsumonji、Orie Okada、Akira Tsubouchi、Takeshi Takeda

  DOI：10.1016/j.tet.2006.08.001

  日期：2006.10

  (E)-Alkenyl halides were transformed into (E)-alkenyl sulfides by the nickel(0) triethyl phosphite complex-catalyzed reaction with thiols, whereas (Z)-alkenyl halides gave alkynes under the same reaction conditions. Aryl halides were also transformed into aryl sulfides using the same reagent system.

  （E）-烯基卤化物通过亚磷酸镍（0）三乙基亚乙基配合物与硫醇的反应转化为（E）-烯基硫化物，而在相同反应条件下，（Z）-烯基卤化物产生炔烃。使用相同的试剂系统，也将芳基卤化物转化为芳基硫醚。