(2E,2'E)-2,2'-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) | 1282615-91-1

• 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: (2E,2'E)-2,2'-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline)
• CAS: 1282615-91-1
• 化学式: C₃₃H₃₆N₂
• 分子量: 460.662
• InChiKey: MPJSSWUWBHEECB-MKJCYJKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,3,3-三甲基-2-亚甲基吲哚啉 、 肉桂醛 以 乙醇 为溶剂， 以42%的产率得到(2E,2'E)-2,2'-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline)
  参考文献：
  名称：

  Novel unsymmetrical leuco-TAM, (2E, 2′E)-2,2′-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives: Synthesis and structure elucidation

  摘要：

  Novel unsymmetrical leuco-TAM, (2E, 2'E)-2,2'-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives were synthesized from a reaction of commercially available 2-methylene-1,3,3-trimethylindoline (FB) and substituted cinnamaldehyde derivatives. The chemical structures of the resulting molecules were determined using 1D and 2D NMR spectroscopy experiments, including COSY, HMBC and NOESY. The compounds had the EEE configuration and were potent precursors for Cy5 TAM(+) dyes. This is different from the Malachite green FB-analogs, which generally have a ZE configuration and are precursors to Cy3 TAM(+) dyes. The formation of unsymmetrical LTAM molecules as the sole product suggests that the Michael-type addition of a FB molecule occurs on the delta-carbon of the alpha, beta, gamma, delta-unsaturated imminium salts, which were formed as an intermediate at the first step. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.01.002