2-(2,2-dichloro-1-methylvinyl)benzenethiol | 167558-62-5

• 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-(2,2-dichloro-1-methylvinyl)benzenethiol
• 英文别名: 1,1-Dichloro-2-(o-mercaptophenyl)propene；2-(1,1-Dichloroprop-1-en-2-yl)benzenethiol
• CAS: 167558-62-5
• 化学式: C₉H₈Cl₂S
• 分子量: 219.135
• InChiKey: WFSXPNGYDJSDEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,2-dichloro-1-methylvinyl)benzenethiol 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 3.0h， 生成 2-甲基苯并噻吩 、 3-甲基苯噻吩
  参考文献：
  名称：

  Electrophilic Reactions of Carbenoids. Synthesis of Fused Heterocyclic Systems via Intramolecular Nucleophilic Substitution of Carbenoids

  摘要：

  Intramolecular nucleophilic substitution of carbenoids with oxygen, nitrogen, and sulfur nucleophiles leading to the synthesis of fused heterocyclic compounds has been studied. For the purpose of this investigation styryl type gem-dihalides 4, 8, 18, 20, 28 containing a nucleophilic substituent in the ortho position of the aromatic ring have been synthesized. Carbenoids have been generated in those systems by the halogen-metal exchange reaction and shown to readily undergo intramolecular nucleophilic substitution by the properly located nucleophilic group (OH, SH, or NH2). As a result a new synthetic route to benzofurans, thianaphthenes, and indoles has been established based on nucleophilic substitution of vinyl halides by an ortho substituent. The dramatic increase of reactivity of vinyl halides upon introduction of lithium has been explained as being due to metal-assisted ionization.

  DOI：

  10.1021/jo00122a046
• 作为产物：
  描述：

  (1-tert-butylsulfanyl)-2-(2,2-dichloro-1-methylvinyl)benzenethiol 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以69%的产率得到2-(2,2-dichloro-1-methylvinyl)benzenethiol
  参考文献：
  名称：

  苯并噻吩类的高效合成一个不寻常的钯催化乙烯基类Ç ？S型联轴器

  摘要：

  同时施工一个C  S和一个C 催化条件下C键形成从不同地官能化的苯并噻吩的高效路由的基础宝石-dihalovinyl苯硫酚。与c 可以在此串联与有机硼试剂催化工艺来形成C键为显示在方案（R 1 = H中，Me，F，氯，溴， OCH 2 ö  ; R 2 = H中，Me; R 3＝芳基，杂芳基，烯基，烷基），或通过Heck或Sonogashira与烯烃或炔烃偶联。

  DOI：

  10.1002/anie.200902843

文献信息

• Electrophilic Reactions of Carbenoids. Synthesis of Fused Heterocyclic Systems via Intramolecular Nucleophilic Substitution of Carbenoids
  作者：Marek Topolski

  DOI：10.1021/jo00122a046

  日期：1995.9

  Intramolecular nucleophilic substitution of carbenoids with oxygen, nitrogen, and sulfur nucleophiles leading to the synthesis of fused heterocyclic compounds has been studied. For the purpose of this investigation styryl type gem-dihalides 4, 8, 18, 20, 28 containing a nucleophilic substituent in the ortho position of the aromatic ring have been synthesized. Carbenoids have been generated in those systems by the halogen-metal exchange reaction and shown to readily undergo intramolecular nucleophilic substitution by the properly located nucleophilic group (OH, SH, or NH2). As a result a new synthetic route to benzofurans, thianaphthenes, and indoles has been established based on nucleophilic substitution of vinyl halides by an ortho substituent. The dramatic increase of reactivity of vinyl halides upon introduction of lithium has been explained as being due to metal-assisted ionization.
• Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic CS Coupling
  作者：Christopher S. Bryan、Julia A. Braunger、Mark Lautens

  DOI：10.1002/anie.200902843

  日期：2009.9.7

  construction of a CS and a CC bond under catalytic conditions forms the basis of an efficient route to diversely functionalized benzothiophenes from gem‐dihalovinyl thiophenols. The CC bond can be formed in this tandem catalytic process with an organoboron reagent as shown in the scheme (R1=H, Me, F, Cl, Br, OCH2O; R2=H, Me; R3=aryl, heteroaryl, alkenyl, alkyl), or by Heck or Sonogashira coupling with an

  同时施工一个C  S和一个C 催化条件下C键形成从不同地官能化的苯并噻吩的高效路由的基础宝石-dihalovinyl苯硫酚。与c 可以在此串联与有机硼试剂催化工艺来形成C键为显示在方案（R 1 = H中，Me，F，氯，溴， OCH 2 ö  ; R 2 = H中，Me; R 3＝芳基，杂芳基，烯基，烷基），或通过Heck或Sonogashira与烯烃或炔烃偶联。