(2E,2'E)-2,2'-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(5-chloro-1,3,3-trimethylindoline) | 1282615-92-2

• 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: (2E,2'E)-2,2'-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(5-chloro-1,3,3-trimethylindoline)
• 英文别名: (2E)-5-chloro-2-[(E,5E)-5-(5-chloro-1,3,3-trimethylindol-2-ylidene)-2-phenylpent-3-enylidene]-1,3,3-trimethylindole
• CAS: 1282615-92-2
• 化学式: C₃₃H₃₄Cl₂N₂
• 分子量: 529.552
• InChiKey: GKIXKJCXCHBAPH-ILWANSRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯-1,3,3-三甲基-2-亚甲基吲哚啉 、 肉桂醛 以 乙醇 为溶剂， 以46%的产率得到(2E,2'E)-2,2'-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(5-chloro-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

文献信息

• Unsymmetric leuco-TAM dyes, (2E, 2′E)-2,2′-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives. Part II: X-ray crystal structure
  作者：Sam-Rok Keum、So-Young Ma、Do-Kyung Kim、Hyun-Woo Lim、Se-Jung Roh

  DOI：10.1016/j.dyepig.2012.02.007

  日期：2012.9

  unequivocal solid-state structure and stereochemistry of the unsymmetric leuco-triarylmethane (Un-LTAM) dye 2,2′-(E)-4-(phenyl)pent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives were established using X-ray single-crystal analysis. The X-ray analysis showed that the EEE isomers were formed stereoselectively with an unsymmetric three-bladed propeller conformation from the reaction of a Fischer's

  不对称隐色三芳基甲烷（Un-LTAM）染料2,2'-（E）-4-（苯基）戊-2-烯-1,5-二亚甲基} bis（1）的明确固态结构和立体化学使用X射线单晶分析确定了（3,3-三甲基二氢吲哚）衍生物。X射线分析表明，由Fischer碱和肉桂醛衍生物反应生成的EEE异构体具有不对称的三叶螺旋桨构象，是立体选择性地形成的。5,5'-二氯-4”-硝基三芳基甲烷染料显示三斜晶结构，空间群为P-1。分子交替堆叠形成二聚体，环B和C的分子间距离分别为8.53和9.40Å。这些染料的氧化形式不对称的三芳基甲烷阳离子在680 nm处具有紫外线吸收，并且选定的示例在接近IR区域吸收。
• 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
  作者：Sam-Rok Keum、Min-Hyung Lee、So-Young Ma、Do-Kyung Kim、Se-Jung Roh

  DOI：10.1016/j.dyepig.2011.01.002

  日期：2011.9

  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.