ethyl (E)-2-cyano-3-(3-hydroxyphenyl)-2-propenoate | 13229-93-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-2-cyano-3-(3-hydroxyphenyl)-2-propenoate
• 英文别名: ethyl (E)-2-cyano-(3-hydroxyphenyl)-2-propenoate；ethyl 2-cyano-3-(3'-hydroxyphenyl)prop-2-enoate；(E)-ethyl-2-cyano-3-(3-hydroxyphenyl)acrylate；ethyl (E)-2-cyano-3-(3-hydroxyphenyl)acrylate；3t-(3-hydroxy-phenyl)-2-cyano-acrylic acid ethyl ester；3t-(3-Hydroxy-phenyl)-2-cyan-acrylsaeure-aethylester；ethyl (2E)-2-cyano-3-(3-hydroxyphenyl)-2-propenoate；ethyl (E)-2-cyano-3-(3-hydroxyphenyl)prop-2-enoate
• CAS: 13229-93-1
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: BXOFYZLSAUJUQJ-UXBLZVDNSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  402.4±40.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-2-cyano-3-(3-hydroxyphenyl)-2-propenoate 在 ammonium hydroxide 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 22.0h， 生成 1-pentyl-3-[3'-(tetrahydropyran-2-yloxy)phenyl]-3-propynylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Saeed; Khodarahmi; Fradgley, Pharmaceutical Sciences, 1997, vol. 3, # 5-6, p. 265 - 277

  摘要：

  DOI：
• 作为产物：
  描述：

  间羟基苯甲醛 、 氰乙酸乙酯 在 N-甲基哌嗪 作用下， 反应 0.75h， 以92%的产率得到ethyl (E)-2-cyano-3-(3-hydroxyphenyl)-2-propenoate
  参考文献：
  名称：

  在室温下无溶剂条件下醛与 N-甲基哌嗪的 Knoevenagel 缩合的简单、高效和绿色程序

  摘要：

  摘要 芳香族、脂肪族和杂芳香族醛与活性亚甲基化合物如氰乙酸乙酯、丙二腈和氰基乙酰胺的 Knoevenagel 缩合在室温下非常顺利地进行，方法是在 N-甲基哌嗪的存在下，在无溶剂条件下简单地将这些成分混合在一起，收率非常好的 E 配置产品。

  DOI：

  10.1080/00397910802029364

文献信息

• A Simple, Efficient and Green Procedure for the Knoevenagel Condensation of Aldehydes with N-Methylpiperazine at Room Temperature under Solvent-Free Conditions
  作者：Chhanda Mukhopadhyay、Arup Datta

  DOI：10.1080/00397910802029364

  日期：2008.6.20

  Abstract Knoevenagel condensation of aromatic, aliphatic, and heteroaromatic aldehydes with active methylene compounds such as ethylcyanoacetate, malononitrile, and cyanoacetamide proceed very smoothly at room temperature by simply mixing the ingredients together under solvent-free conditions in the presence of N-methylpiperazine in excellent yields of the E-configured products.

  摘要 芳香族、脂肪族和杂芳香族醛与活性亚甲基化合物如氰乙酸乙酯、丙二腈和氰基乙酰胺的 Knoevenagel 缩合在室温下非常顺利地进行，方法是在 N-甲基哌嗪的存在下，在无溶剂条件下简单地将这些成分混合在一起，收率非常好的 E 配置产品。
• Efficient and reusable amine-functionalized polyacrylonitrile fiber catalysts for Knoevenagel condensation in water
  作者：Guowei Li、Jia Xiao、Wenqin Zhang

  DOI：10.1039/c2gc35483g

  日期：——

  A series of new fiber catalysts has been synthesized by aminating a commercially available polyacrylonitrile fiber with polyamines such as diethylenetriamine and triethylenetetramine. These fiber catalysts can efficiently catalyze the Knoevenagel condensation of benzaldehyde and ethyl cyanoacetate in water (yields: 95–98%). The triethylenetetramine aminated fiber catalyst was used to catalyze the condensations of a wide range of aromatic aldehydes and active methylene compounds and in each case, this catalyst performed well with yields higher than 93%. This fiber catalyst also exhibited excellent reusability (up to 21 times) and photostability.

  通过将市售聚丙烯腈纤维与聚胺（如二亚乙基三胺和三亚乙基四胺）进行胺化，合成了一系列新型纤维催化剂。这些纤维催化剂能高效催化苯甲醛与氰乙酸乙酯在水中进行的Knoevenagel缩合反应（产率：95-98%）。三亚乙基四胺胺化纤维催化剂被用于催化多种芳香醛与活性甲基化合物之间的缩合反应，并且每种情况下，该催化剂都表现出色，产率均高于93%。此纤维催化剂还具有优异的重复使用性（可达21次）和光稳定性。
• Knoevenagel condensation catalyzed by a tertiary-amine functionalized polyacrylonitrile fiber
  作者：Guowei Li、Jia Xiao、Wenqin Zhang

  DOI：10.1039/c0gc00877j

  日期：——

  A new fiber catalyst for Knoevenagel condensation has been prepared by aminating a commercially available polyacrylonitrile fiber with N,N-dimethyl-1,3-propanediamine. The fiber catalyst was characterized by elemental analysis, X-ray powder diffraction spectra (XRD), scanning electron microscopy (SEM) and Fourier-transfer infrared spectroscopy (FTIR). The Knoevenagel condensation proceeded smoothly in the presence of the fiber catalyst and the products were obtained in excellent yields. This catalyst is applicable to a wide range of aromatic aldehydes. Moreover, the reaction can be easily carried out in different solvents of varying polarities. The newly developed fiber catalyst was also found to exhibit excellent recyclability and reusability (up to 10 times) without any additional treatment.

  一种新的纤维催化剂用于Knoevenagel缩合反应，其制备方法是用N,N-二甲基-1,3-丙二胺对商业化的聚丙烯腈纤维进行氨基化。该纤维催化剂通过元素分析、X射线粉末衍射谱（XRD）、扫描电子显微镜（SEM）和傅里叶变换红外光谱（FTIR）进行了表征。在纤维催化剂的促进下，Knoevenagel缩合反应顺利进行，并且得到的产物产率极高。该催化剂适用于多种芳香醛。此外，该反应可以在不同极性的溶剂中容易地进行。新开发的纤维催化剂还表现出优异的可回收性和重复使用性（可达10次），且无需额外处理。
• Solvent-Free Microwave Enhanced Knoevenagel Condensation of Ethyl Cyanoacetate with Aldehydes
  作者：Alok Kumar Mitra、Aparna De、Nilay Karchaudhuri

  DOI：10.1080/00397919908086438

  日期：1999.8

  Abstract A high yielding and fast method of Knoevenagel condensation of ethyl cyanoacetate with various aldehydes under microwave irradiation using environment-friendly ammonium acetate in the absence of any solvent is described.

  摘要 描述了一种在无任何溶剂的情况下，使用环保型醋酸铵，在微波辐射下，氰乙酸乙酯与各种醛的Knoevenagel 缩合反应的高收率和快速方法。
• COPOLYMER AND OPTICAL FILM USING SAME
  申请人：Tosoh Corporation

  公开号：EP3553097A1

  公开（公告）日：2019-10-16

  Provided are a novel copolymer which is expected to form an optical film that has excellent retardation characteristics such as high retardation even in a thin film and an optical film using the same. A copolymer comprising a residue unit A represented by the general formula (1) and a residue unit B represented by the general formula (2): wherein R1 and R2 each independently represent hydrogen (provided that the case where R1 and R2 are both hydrogen is eliminated), a cyano group, an ester group (-C(=O)OX1), an amide group (-C(=O)N(X2)(X3)), or an acyl group (-C(=O)X4) (where X1 to X3 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, and X4 represents a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic group having 3 to 14 carbon atoms); R3 to R7 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, a cyclic group having 3 to 14 carbon atoms, a halogen, a hydroxy group, a carboxy group, a nitro group, a cyano group, an alkoxy group (-OX5), an ester group (-C(=O)OX6), an amide group (-C(=O)N(X7)(X8)), an acyl group (-C(=O)X9), an amino group (-N(X10)(X11)), or a sulfonic acid group (-SOOX12) (where X5 to X8 each independently represent a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms, X9 to X12 each independently represent hydrogen, a linear alkyl group having 1 to 12 carbon atoms, a branched alkyl group having 1 to 12 carbon atoms, or a cyclic alkyl group having 3 to 6 carbon atoms); and adjacent substituents among R3 to R7 may form a fused ring structure each other, wherein R8 represents an m-membered heterocyclic residue containing one or more heteroatoms or a 5-membered or 6-membered ring residue containing no heteroatom (provided that, when R8 is a 6-membered ring residue containing no heteroatom, at least one of R3 to R7 in the general formula (1) represents a hydroxy group), and m represents an integer of 5 to 10; and the m-membered heterocyclic residue, the 5-membered ring residue, and the 6-membered ring residue may form a fused ring structure.

  本发明提供了一种新型共聚物，该共聚物可望形成一种光学薄膜，该光学薄膜具有优异的延缓特性，例如即使在薄膜中也具有高延缓性，本发明还提供了使用该共聚物的光学薄膜。 由通式（1）表示的残留单元 A 和通式（2）表示的残留单元 B 组成的共聚物： 其中 R1 和 R2 各自独立地代表氢（前提是排除 R1 和 R2 都是氢的情况）、氰基、酯基（-C(＝O)OX1）、酰胺基（-C(＝O)N(X2)(X3)）或酰基（-C(＝O)X4）（其中 X1 至 X3 各自独立地代表具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基或具有 3 至 6 个碳原子的环状烷基，而 X4 代表具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基或具有 3 至 14 个碳原子的环状基团）；R3 至 R7 各自独立地代表氢、具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基、具有 3 至 14 个碳原子的环基、卤素羟基、羧基、硝基、氰基、烷氧基 (-OX5)、酯基 (-C(=O)OX6)、酰胺基 (-C(=O)N(X7)(X8))、酰基 (-C(=O)X9)、氨基 (-N(X10)(X11))、或磺酸基（-SOOX12）（其中 X5 至 X8 各自独立地代表具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基或具有 3 至 6 个碳原子的环状烷基，X9 至 X12 各自独立地代表氢、具有 1 至 12 个碳原子的直链烷基、具有 1 至 12 个碳原子的支链烷基或具有 3 至 6 个碳原子的环状烷基）；R3 至 R7 中的相邻取代基可相互形成融合环结构、 其中 R8 代表含有一个或多个杂原子的 m 元杂环残基或不含杂原子的 5 元或 6 元环残基（条件是，当 R8 是不含杂原子的 6 元环残基时，通式（1）中 R3 至 R7 中至少有一个代表羟基），且 m 代表 5 至 10 的整数；且 m 元杂环残基、5 元环残基和 6 元环残基可形成融合环结构。