phenyl 4-nitrocinnamate | 69693-41-0

• 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: phenyl 4-nitrocinnamate
• 英文别名: Phenyl p-nitrocinnamate；phenyl 3-(4-nitrophenyl)prop-2-enoate
• CAS: 69693-41-0
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: MXBRQCBBXUPJDK-UHFFFAOYSA-N

物化性质

• 沸点：
  422.2±24.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl 4-nitrocinnamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以87%的产率得到phenyl 3-(4-aminophenyl)propionate
  参考文献：
  名称：

  Development of tryptase inhibitors derived from thalidomide

  摘要：

  A novel series of tryptase inhibitors with a N-phenylphthalimide skeleton structurally derived from thalidomide (1) has been developed. Structure-activity relationship studies led to a potent and selective tryptase inhibitor, 2-(4-cyanophenyl) isoindole-1,3-dione-5-yl 3-(2-aminopyridin-5-yl) propanoate (7), with the IC50 value of 78 nM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.037
• 作为产物：
  描述：

  对硝基肉桂酸 、 苯酚 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 phenyl 4-nitrocinnamate
  参考文献：
  名称：

  Development of tryptase inhibitors derived from thalidomide

  摘要：

  A novel series of tryptase inhibitors with a N-phenylphthalimide skeleton structurally derived from thalidomide (1) has been developed. Structure-activity relationship studies led to a potent and selective tryptase inhibitor, 2-(4-cyanophenyl) isoindole-1,3-dione-5-yl 3-(2-aminopyridin-5-yl) propanoate (7), with the IC50 value of 78 nM. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.037

文献信息

• Silver-catalyzed direct regioselective phosphonation of β-aryl-α, β-unsaturated carbonyl compounds with H-phosphites under microwave irradiation
  作者：Jin-Wei Yuan、Yuan-Zhe Li、Wen-Peng Mai、Liang-Ru Yang、Ling-Bo Qu

  DOI：10.1016/j.tet.2016.04.034

  日期：2016.6

  An efficient protocol for silver-catalyzed direct radical phosphonation of β-aryl-α,β-unsaturated carbonyl compounds with H-phosphites to afford trans-substituted alkenylphosphonates under microwave irradiation is described. Some notable features of this method are high efficiency, good yield, broad functional groups tolerance, commercially available and cheap catalyst.

  描述了在微波辐射下银催化β-芳基-α，β-不饱和羰基化合物与H-亚磷酸酯进行直接膦酸酯化以提供反式取代的烯基膦酸酯的有效方案。该方法的一些显着特征是高效，高收率，宽泛的官能团耐受性，可商购和廉价的催化剂。
• Influence of Electronically and Sterically Tunable Cinnamate Ligands on the Spectroscopic, Kinetic, and Thermodynamic Properties of Bis(triphenylphosphine)palladium(0) Olefin Complexes
  作者：Magnus R. Buchner、Bettina Bechlars、Bernhard Wahl、Klaus Ruhland

  DOI：10.1021/om200849n

  日期：2012.1.23

  A detailed study of the influence of electronic and steric characteristics of cinnamic acid esters on the spectroscopic, kinetic, and thermodynamic properties of bis(triphenylphosphine)palladium(0) cinnamic acid ester complexes is presented (51 different new complexes included). These complexes show a dynamic behavior on the NMR spectroscopic time scale. Therefore, the rotational barriers of the olefin

  本文详细介绍了肉桂酸酯的电子和空间特性对双（三苯基膦）钯（0）​​肉桂酸酯配合物（包括51种不同的新配合物）的光谱，动力学和热力学性质的影响。这些络合物在NMR光谱时间尺度上显示出动态行为。因此，可以确定烯烃围绕金属-烯烃键的旋转势垒以及烯烃的离解熵和焓以及离解机理。这些发现与NMR光谱，IR光谱和X射线结构数据（包括7个新结构）一起通过Hammett图解释了有关不同烯烃配体对复杂性质的影响。
• Amino- or guanidino-phenylpropionic acid derivatives
  申请人：Torii & Co., Ltd.

  公开号：US04182897A1

  公开（公告）日：1980-01-08

  Amino- or guanidino-phenylpropionic ester derivatives represented by the formula: ##STR1## wherein R is --NH.sub.2 or ##STR2## R.sup.1 is hydrogen or a lower alkyl group, and R.sup.2 is an unsubstituted or a lower-alkyl-, carboxyalkyl-, lower-alkoxy-, lower-alkoxycarbonyl- or halogen-substituted phenyl group or an unsubstituted or a halogen-substituted naphthyl group, and acid addition salts thereof are novel compounds exhibiting a specific enzyme-inhibitory activity to proteolytic enzymes and, therefore, they are useful as the therapeutic agent of diseases induced by abnormal activation of these enzymes. The above-mentioned compounds can be produced by subjecting a nitrocinnamic acid derivative represented by the formula: ##STR3## and a phenol derivative or a naphthol derivative represented by the formula: HO--R.sup.2 to an esterification in the conventional manner to obtain a nitrocinnamic ester derivative, then reducing the latter compound to obtain an aminophenylpropionic ester derivative and, if desired, reacting it with cyanamide to obtain a guanidino-phenylpropionic ester derivative and, if desired, further converting the reaction product to an acid addition salt.

  化合物的名称为氨基或胍基苯丙酸酯衍生物，化学式为：##STR1## 其中，R为—NH2或##STR2## R1为氢或较低烷基，R2为未取代或取代为较低烷基、羧基烷基、较低烷氧基、较低烷氧羰基或卤素的苯基或未取代或取代为卤素的萘基，以及它们的酸加成盐是一种新型化合物，具有特定的酶抑制活性，对蛋白酶酶有抑制作用，因此它们可用于治疗由这些酶的异常活化引起的疾病。上述化合物可以通过将化学式为：##STR3## 的硝基肉桂酸衍生物和化学式为：HO—R2的苯酚衍生物或萘酚衍生物进行酯化反应以得到硝基肉桂酸酯衍生物，然后还原后得到氨基苯丙酸酯衍生物，如果需要，可以与氰胺反应得到胍基苯丙酸酯衍生物，如果需要，还可以进一步将反应产物转化为酸加成盐。
• Development of tryptase inhibitors derived from thalidomide
  作者：Masashi Tetsuhashi、Minoru Ishikawa、Mariko Hashimoto、Yuichi Hashimoto、Hiroshi Aoyama

  DOI：10.1016/j.bmc.2010.05.037

  日期：2010.7

  A novel series of tryptase inhibitors with a N-phenylphthalimide skeleton structurally derived from thalidomide (1) has been developed. Structure-activity relationship studies led to a potent and selective tryptase inhibitor, 2-(4-cyanophenyl) isoindole-1,3-dione-5-yl 3-(2-aminopyridin-5-yl) propanoate (7), with the IC50 value of 78 nM. (C) 2010 Elsevier Ltd. All rights reserved.