E-1-bromo-2-phenylthioethene | 17101-82-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: E-1-bromo-2-phenylthioethene
• 英文别名: [(E)-2-bromoethenyl]sulfanylbenzene
• CAS: 17101-82-5
• 化学式: C₈H₇BrS
• 分子量: 215.114
• InChiKey: CMKYELZKLNNTTC-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  E-1-bromo-2-phenylthioethene 在 双氧水 作用下， 生成 trans-β-Bromovinyl phenyl sulfone
  参考文献：
  名称：

  Kataev,E.G. et al., Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1948 - 1952

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基乙烯基硫醚 在 氯仿 、 溴 作用下， 生成 E-1-bromo-2-phenylthioethene
  参考文献：
  名称：

  Angeletti et al., Gazzetta Chimica Italiana, 1957, vol. 87, p. 1086,1098

  摘要：

  DOI：

文献信息

• A stereospecific route to olefins through sequential coupling reaction of Grignard reagents with 1-bromo-2-phenylthioethene in the presence of nickel or palladium catalysts
  作者：Vito Fiandanese、Giuseppe Marchese、Francesco Naso、Ludovico Ronzini

  DOI：10.1039/c39820000647

  日期：——

  temperature sequential formation of two C–C bonds by reaction of aromatic or aliphatic Grignard reagents with (E)- or (Z)-1-bromo-2-phenylthioethene in the presence of nickel(II) or palladium(II) catalysts provides a novel stereospecific route to a variety of (E)- or (Z)-olefins of the R–CHCH–R and R1–CHCH–R2 type, with a stereoselectivity higher than 99% for the (E) isomers and in the range 95–98% or the (Z)

  在镍（II）或钯（II）催化剂存在下，通过芳族或脂肪族格氏试剂与（E）-或（Z）-1-溴-2-苯硫基乙烯的反应，在室温下顺序形成两个CC键提供了一种新颖的立体定向途径，可合成多种R–CH CH–R和R 1 –CH CH–R 2类型的（E）或（Z）烯烃，其中（E）的立体选择性高于99％异构体，范围为95–98％或（Z）异构体。
• Halodecarboxylation of α,β-acetylenic and α,β-ethylenic acids
  作者：Fadi Homsi、Gérard Rousseau

  DOI：10.1016/s0040-4039(99)00021-0

  日期：1999.2

  Reaction of bis(collidine)iodine(I) (or bromine (I)) hexafluorophosphate with acetylenic acids led to the corresponding iodo(or bromo)acetylenes in high yields. This halodecarboxylation reaction was also observed with acrylic acids substituted in position 3 by an aryl group or an heteroatom.

  双（可力丁）碘（I）（或溴（I））六氟磷酸酯与乙炔酸的反应可高产率地生成相应的碘（或溴）乙炔。还观察到该卤代羧化反应是在3位上被芳基或杂原子取代的丙烯酸。
• Reactions of 2-halovinyl aryl sulfoxides with organometallic reagents
  作者：Cosimo Cardellicchio、Vito Fiandanese、Francesco Naso

  DOI：10.1021/jo00032a023

  日期：1992.3

  (E)- and (Z)-2-halovinyl aryl sulfoxides 1-4 were subjected to reactions with organocopper, organomagnesium, or organolithium reagents. The organometallic reagents gave different products: diorganocuprates led to formation of carbon-carbon bond, with production of alkenyl sulfoxides 5-10, whereas formation of carbon-sulfur bond and production of diaryl or aryl alkyl sulfoxides 11-13 were observed in the reaction with the other organometallics. Possible mechanisms for the two observed processes are briefly discussed.

  (E)-和(Z)-2-卤代aryl硫氧 Identify的化合物1-4，在与有机铜、有机镁或有机锂试剂的反应中生成了不同的产物。前者生成二组分 cuprate，导致碳碳键的形成，生成烯基硫氧杂环化合物5-10。而其他类型的有机金属试剂则导致碳硫键的生成以及 diaryl 或 aryldikyl 硫氧杂环化合物11-13的存在。文中简要讨论了这两种观察到的反应机制的可能性。
• Stereospecific synthesis of alkenyl sulphides by cross-coupling reactions of secondary alkyl Grignard reagents with Z- or E-1-bromo-2-phenylthioethene in the presence of transition metal catalysts
  作者：Vito Fiandanese、Giovanni Miccoli、Francesco Naso、Ludovico Ronzini

  DOI：10.1016/0022-328x(86)80321-7

  日期：1986.10

  Z- and E-1-bromo-2-phenylthioethenes were cross-coupled stereospecifically with s-alkyl Grignard reagents in the presence of a series of NiII, PdII or FeIII catalysts with the aim of finding a catalyst which would not cause s-alkyl → n-alkyl isomerization. With PdCl2(dppf) (dppf = 1,1′-bis(diphenylphosphino)ferrocene) and NiCl2(dppe) (dppe = 1,2-bis(diphenylphosphino)ethane) there was still some isomerization

  在一系列Ni II，Pd II或Fe III催化剂的存在下，将Z-和E -1-溴-2-苯基硫代乙烯与s-烷基格氏试剂进行立体定向交联，目的是发现不会引起氧化的催化剂。仲烷基→正烷基异构化。在PdCl 2（dppf）（dppf = 1,1'-双（二苯基膦基）二茂铁）和NiCl 2（dppe）（dppe = 1,2-双（二苯基膦基）乙烷）的情况下，仍然有一些异构化作用，但完全是异构化的通过使用铁（III）催化剂抑制。
• Stereoselective Syntheses of Conjugated 1-Phenylthio-1,3-alkadienes and 1,3,5-Alkatrienes through the Palladium-Catalyzed Cross-Coupling Reaction of (<i>E</i>)- or (<i>Z</i>)-1-Alkenylboronates with (<i>E</i>)- or (<i>Z</i>)-2-Bromo-1-phenylthio-1-alkenes
  作者：Tatsuo Ishiyama、Norio Miyaura、Akira Suzuki

  DOI：10.1246/cl.1987.25

  日期：1987.1.5

  1-Phenylthio-1,3-alkadienes and 1,3,5-alkatrienes are obtained in excellent yields stereo- and regioselectively by the cross-coupling between 1-alkenyl or 1,3-alkadienyl-1,3,2-benzodioxaboroles and (E)- or (Z)-2-bromo-1-phenylthio-1-alkenes in the presence of a catalytic amount of Pd(PPh3)4. These sulfides are converted to the corresponding conjugated alkatrienes and tetraenes by the reaction with Grignard

  通过 1-链烯基或 1,3-链二烯基-1,3,2-苯并二氧杂环戊烷和(E)- 或 (Z)-2-bromo-1-phenylthio-1- 烯烃在催化量的 Pd(PPh3)4 存在下。这些硫化物在镍催化剂存在下通过与格氏试剂反应转化为相应的共轭烷三烯和四烯。