1-methyl-2,3-bis(methylthio)indole | 120517-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-methyl-2,3-bis(methylthio)indole
• 英文别名: 1-methyl-2,3-dimethylthioindole；1-Methyl-2,3-bis(methylsulfanyl)indole
• CAS: 120517-34-2
• 化学式: C₁₁H₁₃NS₂
• 分子量: 223.363
• InChiKey: WONOZSXVNUWCNY-UHFFFAOYSA-N

物化性质

• 熔点：
  <20 °C
• 沸点：
  362.0±27.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-2,3-bis(methylthio)indole 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以50%的产率得到2,3-dimethylsulfonyl-1-methylindole
  参考文献：
  名称：

  Gilow, Helmuth M.; Brown, Christopher S.; Copeland, John N., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 1025 - 1034

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基吲哚 、 1-(methylthio)morpholine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到1-methyl-2,3-bis(methylthio)indole
  参考文献：
  名称：

  Gilow, Helmuth M.; Brown, Christopher S.; Copeland, John N., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 4, p. 1025 - 1034

  摘要：

  DOI：

文献信息

• Acid-catalysed isomerization of indol-3-yl sulphides to indol-2-yl sulphides: unexpected intermolecular nature of the rearrangement
  作者：Pierre Hamel、Yves Girard、Joseph G. Atkinson

  DOI：10.1039/c39890000063

  日期：——

  The rearrangement of indol-3-yl sulphides (1) to indol-2-yl sulphides (4), catalysed by proton acids, unexpectedly proceeds by an intermolecualr mechanism involving initial disproportionation to an indole-2,3-diyl bis-sulphide (2) and an indole (3), followed by a reaction between (2) and (3) to yield the rearranged product (4).

  质子酸催化的吲哚-3-基硫醚（1）重排为吲哚-2-基硫醚（4），是通过分子间机理意外地进行的，该分子间机理涉及初始歧化成吲哚-2,3-二烷基二硫化物（2）和吲哚（3），然后（2）和（3）之间反应，得到重排产物（4）。
• 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.
• Reactions of 2-lithiated indoles with elemental sulfur. Formation of pentathiepino[6,7-b]indoles and indoline-2-thiones
  作者：Gordon W Rewcastle、Tomasz Janosik、Jan Bergman

  DOI：10.1016/s0040-4020(01)00660-3

  日期：2001.8

  The reactions of 2-lithiated indole and 1-methylindole with elemental sulfur have been studied, leading e.g. to a rational approach to pentathiepino[6,7-b]indoles 5 and 10. Notable amounts of the previously known tetrathiocino[5,6-b:8,7-b ' ]diindole 11 could be observed as a side reaction in the preparation of 10. Treatment of the anions of indoline-2-thiones 6 or 7 with sulfur also gave the pentathiepins 5 or 10, respectively. In addition, a convenient and clean lithiation route to indoline-2-thione (6) has been developed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• HAMEL, PIERRE;GIRARD, YVES;ATKINSON, JOSEPH G., J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 63-65
  作者：HAMEL, PIERRE、GIRARD, YVES、ATKINSON, JOSEPH G.

  DOI：——

  日期：——