(E)-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile | 71750-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile
• 英文别名: trans-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile；4-Hydroxy-3-methoxyzimtsaeurenitril；(E)-4-Hydroxy-3-methoxyzimtsaeurenitril；4-hydroxy-3-methoxy-trans-cinnamic acid nitrile；4-Hydroxy-3-methoxy-trans-zimtsaeure-nitril；3-(3-Methoxy-4-hydroxyphenyl)acrylonitrile；(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enenitrile
• CAS: 71750-09-9
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: XLZOBXJSXAVHDP-NSCUHMNNSA-N

物化性质

• 熔点：
  109-110 °C(Solv: ligroine (8032-32-4))
• 沸点：
  342.3±27.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以58%的产率得到γ-(4-Oxy-3-methoxy-phenyl)-propylamin
  参考文献：
  名称：

  Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide

  摘要：

  Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide-stimulated BV-2 microglial cells was determined. While NAMDA at 100 mu M inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by > 50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH4-dependent dimerization of the newly synthesized iNOS monomer. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.033
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylonitrile
  参考文献：
  名称：

  McRae; Vining, Canadian Journal of Research, 1932, vol. 6, p. 409,412

  摘要：

  DOI：

文献信息

• Wittig Olefination Using Phosphonium Tetraphenylborate in the Absence of Additional Base
  作者：Wenhua Huang、Shuang-Hong Zhao、Guang-Ping Dong

  DOI：10.1080/10426507.2014.902827

  日期：2014.12.2

  The thermal decomposition of (substituted methyl)triphenylphosphonium tetraphenylborates, which can also be generated in situ from the corresponding phosphonium halide and NaBPh4, with an aldehyde affords olefins in 22-100% yields. This Wittig olefination does not need use additional base to form phosphorus ylide, and is highly tolerant of benzoic acid.
• Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles
  作者：Phongprapan Nimnual、Jumreang Tummatorn、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1021/acs.joc.5b01305

  日期：2015.9.4

  The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.
• DIBIASE S. A.; LIPISKO B. A.; HAAG A.; WOLAK R. A.; GOKEL G. W., J. ORG. CHEM., 1979, 44, NO 25, 4640-4649
  作者：DIBIASE S. A.、 LIPISKO B. A.、 HAAG A.、 WOLAK R. A.、 GOKEL G. W.

  DOI：——

  日期：——
• Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide
  作者：Jai Woong Seo、Ekaruth Srisook、Hyo Jin Son、Onyou Hwang、Young-Nam Cha、Dae Yoon Chi

  DOI：10.1016/j.bmcl.2005.05.033

  日期：2005.7

  Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide-stimulated BV-2 microglial cells was determined. While NAMDA at 100 mu M inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by > 50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH4-dependent dimerization of the newly synthesized iNOS monomer. (c) 2005 Elsevier Ltd. All rights reserved.
• McRae; Vining, Canadian Journal of Research, 1932, vol. 6, p. 409,412
  作者：McRae、Vining

  DOI：——

  日期：——