4-{(E)-2-[6'-((E)-2-{5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-thiophen-2-yl}-vinyl)-5'-methyl-[3,3']bipyridinyl-6-yl]-vinyl}-benzonitrile | 651021-82-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-{(E)-2-[6'-((E)-2-{5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-thiophen-2-yl}-vinyl)-5'-methyl-[3,3']bipyridinyl-6-yl]-vinyl}-benzonitrile
• CAS: 651021-82-8
• 化学式: C₃₄H₃₇N₃OSSi
• 分子量: 563.839
• InChiKey: NIZKSJCVQHXDRD-XZBBILGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.29
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  58.8
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-{(E)-2-[6'-((E)-2-{5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-thiophen-2-yl}-vinyl)-5'-methyl-[3,3']bipyridinyl-6-yl]-vinyl}-benzonitrile 在 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以74%的产率得到4-[(E)-2-(6'-{(E)-2-[5-(2-Hydroxy-ethyl)-thiophen-2-yl]-vinyl}-5'-methyl-[3,3']bipyridinyl-6-yl)-vinyl]-benzonitrile
  参考文献：
  名称：

  6-(Arylvinylene)-3-pyridinylboronic esters. Part 2: Versatile building blocks for push–pull nonlinear optical chromophores

  摘要：

  This paper describes a general approach for the synthesis of push-pull 6,6'-disubstituted-3,3'-bipyridine chromophores. As examples, 6-(4-ethanol-2-thienylvinylene)-5-methyl-3-bromopyridine, 6-(4-hydroxy-phenylvinylene)-5-methyl-3-bromopyridine, and the corresponding 3-pyridinylboronic esters have been prepared as building blocks end-capped with electron donor groups (D). 6-(4-Cyano-phenylvinylene)-5-methyl-3-bromopyridine, and 6-(4-cyano-phenylvinylene)-3-bromopyridine have been synthesized as building blocks end-capped with electron acceptor groups (A). {A x D} type cross-couplings via Suzuki reaction gave the push-pull chromophores (I) and (II) in high yields and multigram scales. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01427-8
• 作为产物：
  描述：

  4-氰基苯甲醛 在 四(三苯基膦)钯 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 4-{(E)-2-[6'-((E)-2-{5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-thiophen-2-yl}-vinyl)-5'-methyl-[3,3']bipyridinyl-6-yl]-vinyl}-benzonitrile
  参考文献：
  名称：

  6-(Arylvinylene)-3-pyridinylboronic esters. Part 2: Versatile building blocks for push–pull nonlinear optical chromophores

  摘要：

  This paper describes a general approach for the synthesis of push-pull 6,6'-disubstituted-3,3'-bipyridine chromophores. As examples, 6-(4-ethanol-2-thienylvinylene)-5-methyl-3-bromopyridine, 6-(4-hydroxy-phenylvinylene)-5-methyl-3-bromopyridine, and the corresponding 3-pyridinylboronic esters have been prepared as building blocks end-capped with electron donor groups (D). 6-(4-Cyano-phenylvinylene)-5-methyl-3-bromopyridine, and 6-(4-cyano-phenylvinylene)-3-bromopyridine have been synthesized as building blocks end-capped with electron acceptor groups (A). {A x D} type cross-couplings via Suzuki reaction gave the push-pull chromophores (I) and (II) in high yields and multigram scales. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01427-8