N,N-dimethyl-4-((Z)-((Z)-3-(naphthalen-2-ylmethylene)isobenzofuran-1(3H)-ylidene)methyl)aniline | 1448450-10-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-dimethyl-4-((Z)-((Z)-3-(naphthalen-2-ylmethylene)isobenzofuran-1(3H)-ylidene)methyl)aniline
• CAS: 1448450-10-9
• 化学式: C₂₈H₂₃NO
• 分子量: 389.497
• InChiKey: ANBNGCNJORTQFA-XROAYDFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  16.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  1,3-dihydro-1-(2-naphthalenylmethylene)isobenzofuran 、 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 2.5h， 以93%的产率得到N,N-dimethyl-4-((Z)-((Z)-3-(naphthalen-2-ylmethylene)isobenzofuran-1(3H)-ylidene)methyl)aniline
  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

文献信息

• Solvent-Switched Benzylic Methylene Functionalization: Addition, Ring-Opening, Cyclization, and Unexpected Cleavage of C–O and C–C Bonds
  作者：Deng Yuan Li、Xue Song Shang、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/ol401470y

  日期：2013.8.2

  been achieved using imines as reagents and potassium tert-butoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition/elimination reaction of exo-cyclic enol ethers with imines provides dihydroisobenzofuran derivatives in good yield. In DMSO, an addition/ring-opening/cyclization cascade reaction occurs with unexpected cleavage of C–O and C–C bonds

  使用亚胺作为试剂并使用叔丁醇钾作为催化剂，可以实现环外烯醇醚的分子间苄基亚甲基官能化。根据所使用的溶剂，反应通过两个途径进行。在THF中，的加成/消除反应外切-环烯醇醚与亚胺提供以良好的收率二氢异苯并呋喃衍生物。在DMSO中，加成/开环/环化级联反应会发生意外的C–O和C–C键断裂，从而在环境反应条件下以高收率提供异喹啉-1（2 H）-一产品。
• Transition Metal-Free Cascade Reactions of Alkynols to Afford Isoquinolin-1(2<i>H</i>)-one and Dihydroisobenzofuran Derivatives
  作者：Deng Yuan Li、Ke Ji Shi、Xiao Feng Mao、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/jo5006312

  日期：2014.5.16

  Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.
• 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.