(Z)-1-(4-chloroobenzylidene)-1,3-dihydroisobenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (Z)-1-(4-chloroobenzylidene)-1,3-dihydroisobenzofuran
• 英文别名: (Z)‑1‑(4‑chlorobenzylidene)‑1,3‑dihydroisobenzofuran；(3Z)-3-[(4-chlorophenyl)methylidene]-1H-2-benzofuran
• 化学式: C₁₅H₁₁ClO
• 分子量: 242.705
• InChiKey: NSGXRBGPSDKKQB-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-(4-chloroobenzylidene)-1,3-dihydroisobenzofuran 、 对二甲氨基苯甲醛 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以89%的产率得到4-((Z)-((Z)-3-(4-chlorobenzylidene)isobenzofuran-1(3H)-ylidene)methyl)-N,N-dimethylaniline
  参考文献：
  名称：

  A concise synthesis of tunable fluorescent 1,3-dihydroisobenzofuran derivatives as new fluorophores

  摘要：

  A convenient Potassium tert-butoxide catalyzed addition elimination reaction has been achieved using exo-cyclic end l ethers and aryl aldehydes as the starting materials. The transition-metal free reaction proceeded smoothly to afford 1,3-dihydroisobenzofuran derivatives with good to excellent yields. More importantly, the resulting products were discovered as novel fluorophores with good fluorescence properties and remarkable Stokes shifts. Changing the nature of the substituents in 1,3-dihydroisobenzofurans derivatives allowed the maximum emission wavelengths to be tuned between 438 and 597 nm and the Stokes shifts varied between 63 and 166 nm. In particular, derivative C27 containing a piperidyl and a cyano group showed the maximum emission wavelength of 597 nm and a Stokes shift of 166 nm. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.10.013
• 作为产物：
  描述：

  [2-(4-chlorophenylethynyl)phenyl]methanol 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以87%的产率得到(Z)-1-(4-chloroobenzylidene)-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

  摘要：

  一种高效的无过渡金属合成二氢异苯并呋喃衍生物的方法已被开发，该方法通过介导铯碳酸盐对芳香族炔醇进行分子内氢烷氧化反应。反应以区位选择性进行，专一生成5-exo-dig产物，并且仅观察到新生成双键的Z-异构体。该新方法具有反应条件温和、操作便捷和选择性满意的特点。

  DOI：

  10.1007/s11696-020-01159-5

文献信息

• Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide
  作者：Deng Yuan Li、Ke Ji Shi、Xiao Feng Mao、Zheng Le Zhao、Xin Yan Wu、Pei Nian Liu

  DOI：10.1016/j.tet.2014.06.078

  日期：2014.9
• A concise synthesis of tunable fluorescent 1,3-dihydroisobenzofuran derivatives as new fluorophores
  作者：Xue Song Shang、Deng Yuan Li、Nian Tai Li、Pei Nian Liu

  DOI：10.1016/j.dyepig.2014.10.013

  日期：2015.3

  A convenient Potassium tert-butoxide catalyzed addition elimination reaction has been achieved using exo-cyclic end l ethers and aryl aldehydes as the starting materials. The transition-metal free reaction proceeded smoothly to afford 1,3-dihydroisobenzofuran derivatives with good to excellent yields. More importantly, the resulting products were discovered as novel fluorophores with good fluorescence properties and remarkable Stokes shifts. Changing the nature of the substituents in 1,3-dihydroisobenzofurans derivatives allowed the maximum emission wavelengths to be tuned between 438 and 597 nm and the Stokes shifts varied between 63 and 166 nm. In particular, derivative C27 containing a piperidyl and a cyano group showed the maximum emission wavelength of 597 nm and a Stokes shift of 166 nm. (C) 2014 Elsevier Ltd. All rights reserved.
• Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions
  作者：Shu-Yan Yu、Li-Hong Gao、Jing-Xin Wu、Hong-Bing Lan、Yi Ma、Zhi-Gang Yin

  DOI：10.1007/s11696-020-01159-5

  日期：2020.10

  An efficient, transition-metal-free method to synthesize dihydroisobenzofuran derivatives via intramolecular hydroalkoxylation of aromatic alkynols with the promotion of cesium carbonate has been developed. The reaction proceeds regioselectively with exclusive formation of 5-exo-dig product, and only Z-isomer of the new generated double bond is observed. This new protocol features with milder reaction conditions, more convenient operation and satisfactory selectivities.

  一种高效的无过渡金属合成二氢异苯并呋喃衍生物的方法已被开发，该方法通过介导铯碳酸盐对芳香族炔醇进行分子内氢烷氧化反应。反应以区位选择性进行，专一生成5-exo-dig产物，并且仅观察到新生成双键的Z-异构体。该新方法具有反应条件温和、操作便捷和选择性满意的特点。