1H-吲哚,2-[(4-氯苯基)硫代]- | 139493-28-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 1H-吲哚,2-[(4-氯苯基)硫代]-
• 英文名称: 2-<(4-chlorophenyl)thio>indole
• 英文别名: 2-((4-chlorophenyl)thio)-1H-indole；2-((4-chlorophenyl)thio)indole；2-(4-chlorophenyl)sulfanyl-1H-indole
• CAS: 139493-28-0
• 化学式: C₁₄H₁₀ClNS
• 分子量: 259.759
• InChiKey: SUUOWZPQLXTAJD-UHFFFAOYSA-N

物化性质

• 沸点：
  462.7±25.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4'-二甲氧基二苯二硫 、 1H-吲哚,2-[(4-氯苯基)硫代]- 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2-((4-chlorophenyl)thio)-3-((4-methoxyphenyl)thio)indole
  参考文献：
  名称：

  混合吲哚2，3-双（硫化物）的区域选择性合成。吲哚第二亚磺酰基化机理的研究。

  摘要：

  使用亚磺酰氯进行吲哚的亚磺酰化会导致3-吲哚基硫化物的初步形成，而过量的试剂会在环的2-位引入第二个硫化物。迄今为止，尚未明确阐明第二次亚磺酰化的机理。混合吲哚2，3-双（硫化物）的第一个区域选择性合成的发展已经允许使用不同的亚磺酰氯进行3-吲哚基硫化物的亚磺酰基化的研究。我们的结果提供了证据，表明该反应是通过中间体3,3-二硫代化的吲哚烯进行的，随后其中一个硫化物基团迁移到了2位。

  DOI：

  10.1021/jo951420n
• 作为产物：
  描述：

  4,4'-二氯二苯二硫醚 在 磺酰氯 、 硫代水杨酸 作用下， 以 三氟乙酸 为溶剂， 反应 1.58h， 生成 1H-吲哚,2-[(4-氯苯基)硫代]-
  参考文献：
  名称：

  Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides

  摘要：

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.

  DOI：

  10.1021/jo00100a045

文献信息

• Copper-catalyzed synthesis of 2-sulfenylindoles from indoline-2-thiones and aryl iodides
  作者：Shiping Zhou、Genhua Xiao、Yun Liang

  DOI：10.1016/j.tetlet.2016.12.028

  日期：2017.1

  A novel and efficient method for synthesis of 2-sulfenylindole via copper-catalyzed coupling reaction of indoline-2-thiones with aryl iodides has been developed. A series of N-substituted and N-free 2-sulfenylindole were obtained in high yields. Furthermore, the method was employed to synthesis of benzothieno[2,3-b]indoles from indoline-2-thiones with 1,2-diiodobenzene in the presence of CuI and Pd(OAc)2

  通过铜催化的吲哚-2-硫酮与芳基碘的偶联反应合成2-亚磺酰基吲哚的新方法已经得到了发展。以高收率获得了一系列的N-取代的和不含N的2-亚磺酰基吲哚。此外，该方法用于在CuI和Pd（OAc）2作为催化剂存在下，由吲哚啉-2-硫酮与1,2-二碘代苯合成苯并噻吩并[2,3- b ]吲哚。
• Acid-catalyzed isomerization of 3-indolyl sulfides to 2-indolyl sulfides: first synthesis of 3-unsubstituted 2-arylthioindoles. Evidence for a complex intermolecular process
  作者：Pierre Hamel、Yves Girard、Joseph G. Atkinson

  DOI：10.1021/jo00035a029

  日期：1992.4

  The acid-catalyzed isomerization of 3-indolyl sulfides 1 to the corresponding 2-indolyl sulfides 4 provides the first synthesis of 3-unsubstituted 2-(arylthio)indoles, a hitherto unattainable class of compounds. When catalyzed by trifluoroacetic acid, the isomerization proceeds mainly via an intermolecular mechanism involving initial disproportionation to a 2,3-indolyl bis-sulfide 5 and an unsubstituted counterpart 6 followed by further interaction of these species to yield the rearranged isomer 4. A mechanism is proposed involving a role for the acid in the sulfenyl-transfer steps. This type of process also occurs, to a lesser extent, in the polyphosphoric acid catalyzed isomerization.
• Nonreductive Desulfenylation of 3-Indolyl Sulfides. Improved Syntheses of 2-Substituted Indoles and 2-Indolyl Sulfides
  作者：Pierre Hamel、Nicolas Zajac、Joseph G. Atkinson、Yves Girard

  DOI：10.1021/jo00100a045

  日期：1994.10

  Desulfenylation of 3-indolyl sulfides to the corresponding 3-unsubstituted indoles is usually carried out under reductive conditions, thus accommodating only substituents which are resistant to reduction. We have developed a nonreductive procedure for removal of a sulfide at the 3-position of indoles, using trifluoroacetic acid in the presence of a thiol as trapping agent, which is compatible with a large array of functionalities on the indole ring. In addition, the desulfenylation occurs selectively at the 3-position of the indole, and sulfide groups at other positions of the molecule remain untouched. Thus, indole 2,3-bis-sulfides are selectively desulfenylated at the 3-position, affording 3-unsubstituted 2-indolyl sulfides. This methodology broadens the use of sulfide as a protecting group for the 3-position of indoles.
• Regioselective Synthesis of Mixed Indole 2,3-Bis(sulfides). A Study of the Mechanism of the Second Sulfenylation of Indole
  作者：Pierre Hamel、Patrice Préville

  DOI：10.1021/jo951420n

  日期：1996.1.1

  Sulfenylation of indole using sulfenyl chlorides leads to the initial formation of a 3-indolyl sulfide, while excess reagent introduces a second sulfide at the 2-position of the ring. The mechanism of this second sulfenylation has not, to date, been rigorously elucidated. The development of the first, regioselective synthesis of mixed indole 2,3-bis(sulfides) has allowed the study of the sulfenylation

  使用亚磺酰氯进行吲哚的亚磺酰化会导致3-吲哚基硫化物的初步形成，而过量的试剂会在环的2-位引入第二个硫化物。迄今为止，尚未明确阐明第二次亚磺酰化的机理。混合吲哚2，3-双（硫化物）的第一个区域选择性合成的发展已经允许使用不同的亚磺酰氯进行3-吲哚基硫化物的亚磺酰基化的研究。我们的结果提供了证据，表明该反应是通过中间体3,3-二硫代化的吲哚烯进行的，随后其中一个硫化物基团迁移到了2位。