(Z)-4-(1-methyl-2-phenylvinyl)benzaldehyde | 622378-73-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-4-(1-methyl-2-phenylvinyl)benzaldehyde
• 英文别名: 4-[(Z)-1-phenylprop-1-en-2-yl]benzaldehyde
• CAS: 622378-73-8
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: WSSIEEGHKXAKNQ-QBFSEMIESA-N

物化性质

• 沸点：
  352.2±21.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-4-(1-methyl-2-phenylvinyl)benzaldehyde 在 sodium tetrahydroborate 作用下， 生成 N-[(4-tert-butylphenyl)methyl]-1-[4-[(Z)-1-phenylprop-1-en-2-yl]phenyl]methanamine
  参考文献：
  名称：

  A rotaxane synthesis based on stilbene photoisomerization. A photoswitchable catch and release processElectronic supplementary information (ESI) available: NMR spectra. See http://www.rsc.org/suppdata/cc/b3/b306349f/

  摘要：

  一种以(Z)-α-甲基二苯乙烯为终止剂的 [2]rotaxane (1)通过(E)-到(Z)-二苯乙烯的光异构化过程以良好的收率合成，(2)通过从(Z)-到(E)-二苯乙烯的反向光异构化解离。

  DOI：

  10.1039/b306349f
• 作为产物：
  描述：

  4-(dimethoxymethyl)benzoic acid 在 acid 作用下， 生成 (Z)-4-(1-methyl-2-phenylvinyl)benzaldehyde
  参考文献：
  名称：

  A rotaxane synthesis based on stilbene photoisomerization. A photoswitchable catch and release processElectronic supplementary information (ESI) available: NMR spectra. See http://www.rsc.org/suppdata/cc/b3/b306349f/

  摘要：

  一种以(Z)-α-甲基二苯乙烯为终止剂的 [2]rotaxane (1)通过(E)-到(Z)-二苯乙烯的光异构化过程以良好的收率合成，(2)通过从(Z)-到(E)-二苯乙烯的反向光异构化解离。

  DOI：

  10.1039/b306349f

文献信息

• Using Photoresponsive End-Closing and End-Opening Reactions for the Synthesis and Disassembly of [2]Rotaxanes: Implications for Dynamic Covalent Chemistry
  作者：Yuji Tokunaga、Koichiro Akasaka、Nobuharu Hashimoto、Shou Yamanaka、Kenji Hisada、Youji Shimomura、Suzuka Kakuchi

  DOI：10.1021/jo8025143

  日期：2009.3.20

  We have synthesized two [2]rotaxanes, each possessing a (Z)-alpha-methylstilbene unit as one of its stoppers, in good yield through the photoisomerization of terminal (E)-alpha-methylstilbene units of dialkylammonium sails in the presence of the crown ether dibenzo[24]crown-8 (DB24C8). The synthesis relies on the formation of pseudorotaxane intermediates through hydrogen bond-guided self-assembly and subsequent end-closing photoisomerization. An (E)-alpha-methylstilbene unit is not sufficiently bulky to prevent dissociation of the DB24C8 unit, whereas a (Z)-alpha-methylstilbene unit acts as a true stopper. We also synthesized these [2]rotaxanes from the (Z)-alpha-methylstilbene-teriminated axle-like salts though thermodynamic covalent chemistry by taking advantage of the reversibility of the photoisomerization. To dissociate the components of the [2]rotaxanes, we performed the reverse end-opening process under UV irradiation (i.e., Z-to-E isomerization of the alpha-methylstilbene termini) in a polar solvent. These rotaxanes are stable at room temperature, but dissociate slowly to their two components at elevated temperatures.
• A rotaxane synthesis based on stilbene photoisomerization. A photoswitchable catch and release processElectronic supplementary information (ESI) available: NMR spectra. See http://www.rsc.org/suppdata/cc/b3/b306349f/
  作者：Yuji Tokunaga、Koichiro Akasaka、Kenji Hisada、Youji Shimomura、Suzuka Kakuchi

  DOI：10.1039/b306349f

  日期：——

  A [2]rotaxane, having (Z)-α-methylstilbene as a stopper, is (1) synthesized in good yield by using a (E)- to (Z)-stilbene photoisomerization process, and (2) dissociated by reverse photoisomerization from (Z)- to (E)-stilbene.

  一种以(Z)-α-甲基二苯乙烯为终止剂的 [2]rotaxane (1)通过(E)-到(Z)-二苯乙烯的光异构化过程以良好的收率合成，(2)通过从(Z)-到(E)-二苯乙烯的反向光异构化解离。