4-methoxycinnamic acid p-nitrophenyl ester | 89023-01-8

• 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: 4-methoxycinnamic acid p-nitrophenyl ester
• 英文别名: 3-(4-Methoxy-phenyl)-acrylic acid 4-nitro-phenyl ester；(4-nitrophenyl) (E)-3-(4-methoxyphenyl)prop-2-enoate
• CAS: 89023-01-8
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: YXRNMWCADUELTD-NYYWCZLTSA-N

物化性质

• 沸点：
  500.2±43.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methoxycinnamic acid p-nitrophenyl ester 在 4-二甲氨基吡啶 、 氢溴酸 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 19.17h， 生成 4'-methoxycinnamoyl 8-O-[4-[(tert-butoxycarbonyl)aminomethyl]benzoyl]-A-ring pyrrole-duocarmycin B2
  参考文献：
  名称：

  Synthesis and antitumor activity of duocarmycin derivatives: modification at C-8 position of A-ring pyrrole compounds bearing the simplified DNA-binding groups

  摘要：

  A series of the 8-O-substituted A-ring pyrrole derivatives of duocarmycin bearing the simplified DNA-binding moieties such as cinnamoyl or heteroarylacryloyl groups were synthesized, and evaluated for in vitro anticellular activity against HeLa S-3 cells and in vivo antitumor activity against murine sarcoma 180 in mice. In addition, the stability of the 8-O-substituted analogues in aqueous solution and the conversion to their active form (cyclopropane compound) from the 8-O-substituted analogues in mice or human serum were examined. The 8-O-substituted A-ring pyrrole derivatives bearing the simplified DNA-binding moieties showed remarkably potent in vivo antitumor activity and low peripheral blood toxicity compared with the 8-O-substituted A-ring pyrrole derivatives having the trimethoxyindole skeleton in segment-B (Seg-B), which were equal to 8-O-[(N-methylpiperazinyl)carbonyl] derivatives of 4'-methoxycinnamates and 4'-methoxy-beta-heteroarylacrylates. Moreover, among 8-O-substituted analogues, several compounds can be chemically or enzymatically converted to their active form in human serum. This result indicated that new 8-O-substituted derivatives were different prodrugs from KW-2189 and 8-O-substituted analogues being the same type of prodrug as KW-21S9. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00293-x
• 作为产物：
  描述：

  对硝基苯酚 、 反式-4-甲氧基肉桂酸 在 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到4-methoxycinnamic acid p-nitrophenyl ester
  参考文献：
  名称：

  异硫脲催化的α，β-不饱和对硝基苯基酯的转移加氢

  摘要：

  已开发出使用Hantzsch酯的异硫脲催化的α，β-不饱和对硝基苯酯转移氢化的方案。使用带有吸电子β-取代基的α，β-不饱和芳基酯，观察到良好至优异的产率。可以直接分离出芳基酯产物，以中等至优异的收率（7例，产率为16–98％）或转化为相应的甲酯（2例，产率为68–70％）或苄基酰胺（2例，44-88）。氢化酯与适当的亲核试剂进行原位反应后得到 初步实验表明，当使用手性异硫脲催化剂时，适度的对映体诱导（76:24 er）是可能的。

  DOI：

  10.1016/j.tet.2020.131758

文献信息

• Synthesis and antimycobacterial evaluation of new trans-cinnamic acid hydrazide derivatives
  作者：Samir A. Carvalho、Edson F. da Silva、Marcus V.N. de Souza、Maria C.S. Lourenço、Felipe R. Vicente

  DOI：10.1016/j.bmcl.2007.11.091

  日期：2008.1

  evaluation of new trans-cinnamic acid derivatives of isonicotinic acid series (5) and benzoic acid series (6), designed by exploring the molecular hybridization approach between isoniazid (1) and trans-cinnamic acid derivative (3). The minimum inhibitory concentration (MIC) of the compounds 5a-d and 6c exhibited activity between 3.12 and 12.5 microg/mL and could be a good start point to find new lead compounds

  在这项工作中，我们报告了异烟肼酸系列（5）和苯甲酸系列（6）的新型反式肉桂酸衍生物的合成和抗分枝杆菌的评价，这是通过探索异烟肼（1）和反式肉桂酸之间的分子杂交方法而设计的酸衍生物（3）。化合物5a-d和6c的最低抑菌浓度（MIC）表现出3.12至12.5 microg / mL的活性，并且可能是寻找新的抗多药结核病先导化合物的良好起点。
• Influence of Electronically and Sterically Tunable Cinnamate Ligands on the Spectroscopic Properties and Reactivity of Bis(triphenylphosphine)platinum(0) Olefin Complexes
  作者：Magnus R. Buchner、Bettina Bechlars、Bernhard Wahl、Klaus Ruhland

  DOI：10.1021/om301021j

  日期：2013.3.25

  ester)platinum(0) complexes were synthesized to examine electronic and steric influences on their behavior as inhibited precatalysts and to correlate this with 1H, 13C, 19F, 31P and 195Pt NMR spectroscopic, IR spectroscopic, and X-ray structural properties (9 X-ray structures included). The substituent at the 4-position of the phenyl group proved to be a valuable moiety in controlling the electronic properties

  总共合成了48种新的双（三苯基膦）（肉桂酸酯）铂（0）配合物，以研究电子和空间位阻对其作为受抑制前催化剂的行为的影响，并将其与1 H，13 C，19 F，31 P和195 Pt NMR光谱，IR光谱和X射线结构特性（包括9个X射线结构）。事实证明，苯基4位上的取代基是控制烯烃配体电子特性以及控制金属-配体键强度的重要部分。反应性和NMR光谱数据与该取代基的Hammett参数相关：尤其是偶联常数2 J PP和1 J PPt。配合物的反应性是通过三苯膦的NMR滴定法（1 H NMR；触发配体取代）以及与二苯基硅烷的反应（1 H和29 Si NMR；触发氧化加成）确定的。所确定的平衡与烯烃的电子密度相关。作为一个典型的例子，可以从配合物的NMR 2 J PP偶合常数间接预测反应性，这也可以从相关的Pd配合物中发现。
• Negative-type photosensitive resin composition, pattern forming method, cured film, insulating film, color filter, and display device
  申请人：Shiota Dai

  公开号：US09244346B2

  公开（公告）日：2016-01-26

  A negative-type photosensitive resin composition capable of forming a pattern having favorable adhesiveness at a low light exposure; a pattern forming method using the resin composition; a cured film, an insulating film, a color filter formed using resin composition; and a display device provided with the cured film, insulating film, or color filter. The resin composition contains a compound represented by the following formula (1). In the formula, R1 and R2 each independently indicate a hydrogen atom or an organic group, but at least one indicates an organic group. R1 and R2 may be bonded to form a ring structure and may contain a hetero atom bond. R3 indicates a single bond or an organic group. R4 to R9 each independently indicate a hydrogen atom, an organic group, etc., but R6 and R7 are never hydroxyl groups. R10 indicates a hydrogen atom or an organic group.

  一种负型光敏树脂组合物，能够在低光照下形成具有良好粘附性的图案；使用该树脂组合物的图案形成方法；使用该树脂组合物形成的固化膜、绝缘膜、彩色滤光片；以及具有固化膜、绝缘膜或彩色滤光片的显示装置。该树脂组合物包含以下式（1）所表示的化合物。在该式中，R1和R2各自独立表示氢原子或有机基团，但至少一个表示有机基团。R1和R2可以结合形成环状结构，并且可以含有杂原子键。R3表示单键或有机基团。R4到R9各自独立表示氢原子、有机基团等，但R6和R7永远不是羟基。R10表示氢原子或有机基团。
• DC-88A derivatives
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0354583A1

  公开（公告）日：1990-02-14

  A novel DC-88A derivative represented by general formula: wherein represents or has an excellent antitumor activity and is useful as an antitumor agent.

  由通式表示的新型 DC-88A 衍生物： 其中 代表 或 具有优异的抗肿瘤活性，可用作抗肿瘤药。
• DC-89 derivatives
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0461603A1

  公开（公告）日：1991-12-18

  Novel DC-89 derivatives have an excellent anti-tumor activity, and thus are useful as anti-tumor agent.

  新型 DC-89 衍生物具有出色的抗肿瘤活性，因此可用作抗肿瘤药物。