(2Z)-5-chloro-2-[(3E)-3-(5-chloro-1,3,3-trimethylindol-2-ylidene)-2-phenylpropylidene]-1,3,3-trimethylindole | 1071493-54-3

• 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: (2Z)-5-chloro-2-[(3E)-3-(5-chloro-1,3,3-trimethylindol-2-ylidene)-2-phenylpropylidene]-1,3,3-trimethylindole
• CAS: 1071493-54-3
• 化学式: C₃₁H₃₂Cl₂N₂
• 分子量: 503.514
• InChiKey: FUUDZQJUQNRQKZ-PSUTYVDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2Z)-5-chloro-2-[(3E)-3-(5-chloro-1,3,3-trimethylindol-2-ylidene)-2-phenylpropylidene]-1,3,3-trimethylindole 以 氯仿 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Diastereomeric isomerization of Fischer's base analogs of LTAM molecules in organic solvents: mechanistic investigation

  摘要：

  Three possible mechanistic routes for the diastereomeric isomerization of the leuco-triarymethane (LTAM) molecules have been proposed, depending on the formal breaking of the carbon-carbon double bond via either heterolytic, homolytic or molecula splitting/reassembling. The substituents effects on the rates of the isomerization of the LTAM molecules are not consistent with the heterolytic process. From the negative result in the synthesis of an unsymmetric LTAM from the reaction of symmetric LTAM's and substituted Fischer bases, the process via the molecula splitting/reassembling can also be ruled out.The rates of the isomerizations of the LTAM molecules are decreased up to ten times with various weight percentages of the radical scavenger (RS), comparing to the rate without RS. The radical scavenging effects allow us to confirm that the homolytic process is the most promising mechanistic process for the isomerization of LTAM molecules among three proposed routes. On the basis of Walter's concept, central carbon-centered radicals of LTAM molecules are obviously of the Class S type and hence the isomerization rates are affected by EDG and EWG in the same directions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.080

文献信息

• Unsymmetrically Substituted Leuco-Triarylmethane Molecules Formed from the Reaction of a Fischer's Base and α,β-Unsaturated Iminium Salts via a Michael-Type Reaction
  作者：Sam-Rok Keum、Hyun-Soo Kim、Do-Kyung Kim

  DOI：10.5012/bkcs.2013.34.5.1563

  日期：2013.5.20

  E-mail: [e-mail] January 14, 2013, Accepted February 22, 2013Key Words : Triarylmethane, Malachite green, Carbinol, Michael-type addition, α,β-unsaturated iminium saltsTriarylmethane (TAM) compounds, also known as “leuco-TAM” (LTAM), are used in a variety of chemical, pharma-ceutical, and life science industries, including thermal imag-ing and carbonless copying materials.

  E-mail: [e-mail] January 14, 2013 Accepted February 22, 2013Key Words : 三芳基甲烷、孔雀绿、甲醇、迈克尔型加成、α,β-不饱和亚胺盐三芳基甲烷（TAM）化合物，又称“leuco-TAM” (LTAM) 用于各种化学、制药和生命科学行业，包括热成像和无碳复印材料。
• Diastereomeric isomerization of hetaryl leuco-TAM dyes, (2Z, 2′E)-2,2′-(2-phenyl propane-1,3-diylidene)bis(1,3,3-trimethylindoline) derivatives in various organic solvents
  作者：Sam-Rok Keum、Se-Jung Roh、So-Young Ma、Do-Kyung Kim、Art E. Cho

  DOI：10.1016/j.tet.2010.07.030

  日期：2010.10

  The diastereomeric isomerization of the ZE isomers of (2Z, 2'E)-2,2'-(2-phenyl propane-1,3-diylidene) bis(1,3,3-trimethylindoline) derivatives were examined by H-1 NMR spectroscopy in various organic solvents. In non-polar solvents, such as benzene, THF, and chloroform, the ZE isomers of these molecules equilibrated into a mixture of ZE/EE or ZE/EE/ZZ isomers with time, whereas the isomers were inert in polar organic solvents, such as acetone and DMSO. Theoretical calculations of the energies and dipole moments of the diastereomers in different media were performed using the Jaguar program. (C) 2010 Elsevier Ltd. All rights reserved.