2-氰基-3-(4-甲基苯基)丙烯酸 | 20374-48-5

• 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
• 中文名称: 2-氰基-3-(4-甲基苯基)丙烯酸
• 英文名称: (E)-2-cyano-3-(p-tolyl)acrylic acid
• 英文别名: 2-Cyano-3-(4-methylphenyl)acrylic acid；(E)-2-cyano-3-(4-methylphenyl)prop-2-enoic acid
• CAS: 20374-48-5
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: VSMAAVBAABUVMQ-UXBLZVDNSA-N

物化性质

• 熔点：
  199-202
• 沸点：
  352.5±30.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-氰基-3-(4-甲基苯基)丙烯酸 在 copper(I) oxide 作用下， 生成 (Z)-p-methylcinnamonitrile
  参考文献：
  名称：

  Transmission of substituent effects through extended systems—II. Substituted cis and trans cinnamonitriles

  摘要：

  DOI：

  10.1016/0584-8539(82)80001-9
• 作为产物：
  描述：

  tert-butyl (E)-(4-methylbenzylidene)cyanoacetate 在 三氟乙酸 作用下， 生成 2-氰基-3-(4-甲基苯基)丙烯酸
  参考文献：
  名称：

  Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors

  摘要：

  A novel class of low molecular weight protein tyrosine kinase inhibitors is described. These compounds constitute a systematic series of molecules with a progressive increase in affinity toward the substrate site of the EGF receptor kinase domain. These competitive inhibitors also effectively block the EGF-dependent autophosphorylation of the receptor. The potent EGF receptor kinase blockers examined were found to competitively inhibit the homologous insulin receptor kinase at 10(2)-10(3) higher inhibitor concentrations in spite of the significant homology between these protein tyrosine kinases. These results demonstrate the ability to synthesize selective tyrosine kinase inhibitors. The most potent EGF receptor kinase inhibitors also inhibit the EGF-dependent proliferation of A431/clone 15 cells with little or no effect on EGF independent cell growth. These results demonstrate the potential use of protein tyrosine kinase inhibitors as selective antiproliferative agents for proliferative diseases caused by the hyperactivity of protein tyrosine kinases. We have suggested the name "tyrphostins" for this class of antiproliferative compounds which act as protein tyrosine kinase blockers.

  DOI：

  10.1021/jm00130a020

文献信息

• Heterocyclic Compound
  申请人：Amasaki Ichiro

  公开号：US20100004439A1

  公开（公告）日：2010-01-07

  A compound represented by the following Formula (1): wherein, Het 1 represents a bivalent five- or six-membered aromatic heterocyclic residue and may further be substituted; X a to X d each independently represent a heteroatom and may further be substituted; Y a to Y f each independently represent a heteroatom or a carbon atom and may further be substituted; the ring bound to Het 1 may have a double bond at any position

  以下是您提供的化学公式(1)的中文翻译： 其中，Het1代表一个二价的五元或六元芳香杂环基团，且可以进一步被取代；Xa至Xd每个独立地代表一个杂原子，且可以进一步被取代；Ya至Yf每个独立地代表一个杂原子或一个碳原子，且可以进一步被取代；与Het1相连的环可以在任何位置有一个双键。
• trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines
  作者：Fritz Schömberg、Milica Perić、Maximilian Meyer、Ivan Vilotijević

  DOI：10.1016/j.tet.2021.132457

  日期：2021.10

  the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic

  在 TMSCN 和醇添加剂存在下，ynoates 和ynones 的反式选择性氢氰化反应由亲核膦催化。氰化氢反加成到炔烃的三取代E-烯烃产物具有高区域选择性和立体选择性。醇类添加剂与 TMSCN 反应，原位生成氰化氢。仅在非质子惰性条件下，在 TMSCN 存在下，炔酸经历膦催化的氢氰化。在这些反应中，TMSCN 与酸反应生成氰化氢和甲硅烷基酯，与酸不同，后者经过膦催化氢氰化并在后处理后生成立体定义的E -2-氰基丙烯酸。
• PHOTOSENSITIVE PORPHYRIN DYES FOR DYE-SENSITIZED SOLAR CELLS
  申请人：NATIONAL CHUNG HSING UNIVERSITY

  公开号：US20160005546A1

  公开（公告）日：2016-01-07

  A photosensitive porphyrin-based dye is adapted to be used in a photoelectric converting device such as a dye-sensitized solar cell. The photosensitive porphyrin-based dye has a porphyrin center, at least one electron donor unit, at least one electron acceptor unit and an optional blocker unit wherein the units are directly connected to the porphyrin center or connected to the porphyrin center via ethynyl-bridges.

  一种基于光敏卟啉的染料被改进以在光电转换装置中使用，比如染料敏化太阳能电池。这种基于光敏卟啉的染料具有一个卟啉中心，至少一个电子给体单元，至少一个电子受体单元和一个可选的阻塞单元，其中这些单元直接连接到卟啉中心或通过乙炔桥连接到卟啉中心。
• Acid-catalyzed, regioselective [3 + 3] annulation of enaminones and α-substituted cinnamic acids: access to 3,4-dihydropyridones and 2-piperidinones
  作者：Sivanna Chithanna、Animesh Roy、Ding-Yah Yang

  DOI：10.1039/d1ob01115d

  日期：——

  acid-catalyzed Michael addition of enaminones to electron-deficient α-substituted cinnamic acids followed by lactamization, whereas the latter was synthesized by the same methodology except that cinnamic acids were replaced with coumarin 3-carboxylic acids. A unique regioselective reactivity of the enaminones toward different cinnamic acid derivatives is described.

  报道了一种合成结构多样的 3,4-二氢吡啶酮和 2-哌啶酮的有效策略。前者是通过将烯胺酮与缺电子α-取代的肉桂酸进行酸催化迈克尔加成，然后进行内酰胺化来制备的，而后者是通过相同的方法合成的，只是肉桂酸被香豆素 3-羧酸取代。描述了烯胺酮对不同肉桂酸衍生物的独特区域选择性反应性。
• Dye compounds, and their use in dye-sensitized solar cells
  申请人：Solvay SA

  公开号：EP2765132A1

  公开（公告）日：2014-08-13

  Disclosed are compounds of formula D-B-A-ANC (wherein D is an electron donor group, B is a chromophore group, A is an electron acceptor group, and ANC is an anchoring part comprising at least one anchoring group, and dye-sensitized solar cells (DSSC) incorporating the same as a dye-sensitizer.

  本文披露了公式D-B-A-ANC的化合物（其中D是电子给体基团，B是色团基团，A是电子受体基团，ANC是包含至少一个锚定基团的锚定部分），以及将其作为染料敏化剂的染料敏化太阳能电池（DSSC）。