Phthalimido(triphenylmethyl)disulfane

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Phthalimido(triphenylmethyl)disulfane
• 英文别名: 2-(Trityldisulfanyl)isoindole-1,3-dione
• 化学式: C₂₇H₁₉NO₂S₂
• 分子量: 453.585
• InChiKey: CFPSLNTZGHCECL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-甲基吲哚 、 Phthalimido(triphenylmethyl)disulfane 在 lithium bromide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以61%的产率得到1-methyl-3-(trityldisulfaneyl)-1H-indole
  参考文献：
  名称：

  溴化锂催化吲哚与N-二硫代邻苯二甲酰亚胺之间的C3-二硫化

  摘要：

  开发了一种简单的、绿色卤化物催化的吲哚衍生物与N-二硫代邻苯二甲酰亚胺二硫化反应方案。这种C-H二硫化物反应在室温下以经济的溴化锂为催化剂顺利进行，为合成新型不对称二硫化物提供了一种有效的方法。以高产率获得了一系列具有良好官能团耐受性的3-二硫代吲哚衍生物；此外，广泛的 Harpp 试剂（芳基、苄基、一级、二级、三级）证实了这种方法的实用性。

  DOI：

  10.1021/acs.joc.1c02556
• 作为产物：
  描述：

  三苯甲硫醇 在 二氯化硫 作用下， 以 乙醚 、 正己烷 、 水 为溶剂， 反应 3.0h， 生成 Phthalimido(triphenylmethyl)disulfane
  参考文献：
  名称：

  Structure and chemistry of chloro(triphenylmethyl)sulfanes

  摘要：

  The structures of chloro(triphenylmethyl)mono-, di-, and -trisulfanes were obtained. The monosulfane displayed a triclinic (P1) space group, a = 10.792(2) Angstrom, b = 15.090(2) Angstrom, c = 10.027(2) Angstrom, alpha = 100.15(1)degrees, beta 103.13(1)degrees, gamma = 88.80(1)degrees, Z = 4. The disulfane gave a triclinic (P1) space group, a = 9.758(1) Angstrom, b = 10.426(2) Angstrom, c = 9.1691(6) Angstrom, alpha = 97.52(1)degrees, beta = 90.116(1)degrees, gamma = 116.750(1)degrees, Z = 2. The trisulfane gave an orthorhombic space group (Pna2(1)), a = 9.224(1) Angstrom, b = 19.196(3) Angstrom, c = 10.308(1) Angstrom, Z = 4. The sulfenyl chlorides decompose above their melting points to mixtures consisting primarily of triphenylchloromethane and sulfur. The sulfur was determined to consist of several allotropes (S-6, S-7, S-8, and S-9). The di- and trisulfanes slowly decompose to the same products at room temperature; the decompositions are enhanced by light. The decomposition of the trisulfane in the presence of dienes gave adducts consistent with the transfer of a two-sulfur species. The disulfane and trisulfane undergo the normal nucleophilic substitution reactions of the monosulfanes.

  DOI：

  10.1021/jo00083a022

文献信息

• Structure and chemistry of chloro(triphenylmethyl)sulfanes
  作者：Charles R. Williams、James F. Britten、David N. Harpp

  DOI：10.1021/jo00083a022

  日期：1994.2

  The structures of chloro(triphenylmethyl)mono-, di-, and -trisulfanes were obtained. The monosulfane displayed a triclinic (P1) space group, a = 10.792(2) Angstrom, b = 15.090(2) Angstrom, c = 10.027(2) Angstrom, alpha = 100.15(1)degrees, beta 103.13(1)degrees, gamma = 88.80(1)degrees, Z = 4. The disulfane gave a triclinic (P1) space group, a = 9.758(1) Angstrom, b = 10.426(2) Angstrom, c = 9.1691(6) Angstrom, alpha = 97.52(1)degrees, beta = 90.116(1)degrees, gamma = 116.750(1)degrees, Z = 2. The trisulfane gave an orthorhombic space group (Pna2(1)), a = 9.224(1) Angstrom, b = 19.196(3) Angstrom, c = 10.308(1) Angstrom, Z = 4. The sulfenyl chlorides decompose above their melting points to mixtures consisting primarily of triphenylchloromethane and sulfur. The sulfur was determined to consist of several allotropes (S-6, S-7, S-8, and S-9). The di- and trisulfanes slowly decompose to the same products at room temperature; the decompositions are enhanced by light. The decomposition of the trisulfane in the presence of dienes gave adducts consistent with the transfer of a two-sulfur species. The disulfane and trisulfane undergo the normal nucleophilic substitution reactions of the monosulfanes.
• LiBr-Catalyzed C3-Disulfuration between Indole and <i>N</i>-Dithiophthalimide
  作者：Dungai Wang、Wangyu Li、Keqiang Shi、Yuanjiang Pan

  DOI：10.1021/acs.joc.1c02556

  日期：2023.2.17

  indole derivatives with N-dithiophthalimides has been developed. This C–H disulfide reaction proceeded smoothly at room temperature with economical LiBr as catalyst, providing an effective method for the synthesis of novel unsymmetrical disulfides. A series of 3-dithioindole derivatives were obtained in high yields with good functional group tolerance; moreover, the wide scope of Harpp reagents (aryl

  开发了一种简单的、绿色卤化物催化的吲哚衍生物与N-二硫代邻苯二甲酰亚胺二硫化反应方案。这种C-H二硫化物反应在室温下以经济的溴化锂为催化剂顺利进行，为合成新型不对称二硫化物提供了一种有效的方法。以高产率获得了一系列具有良好官能团耐受性的3-二硫代吲哚衍生物；此外，广泛的 Harpp 试剂（芳基、苄基、一级、二级、三级）证实了这种方法的实用性。