benzyl (E)-3,4-dimethoxycinnamate

• 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: benzyl (E)-3,4-dimethoxycinnamate
• 英文别名: benzyl (E)-3-(3,4-dimethoxyphenyl)acrylate；benzyl (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: JDHVAEUWZWMVOB-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3,4-二甲氧基肉酸酸	3,4-dimethoxy-trans-cinnamic acid	14737-89-4	C11H12O4	208.214
  ——	benzyl 3-(3,4-dimethoxyphenyl)propanoate	——	C18H20O4	300.354

反应信息

• 作为反应物：
  描述：

  benzyl (E)-3,4-dimethoxycinnamate 在 Pd black-(S) 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到3,4-二甲氧基苯丙酸
  参考文献：
  名称：

  Effect of solvent and hydrogen during selective hydrogenation

  摘要：

  Described is the solvent effect for the chemoselective hydrogenation of alkenes having a benzyloxy group (Bn-O-) using a hydrogenation system employing atomic hydrogen permeating through a Pd sheet electrode. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01787-7
• 作为产物：
  描述：

  丙烯酸苄酯 、 2,3-二甲氧基苯甲酸 在 [Ru(O₂CMes)₂(p-cymene)] 、 vanadia 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以52%的产率得到benzyl (E)-3,4-dimethoxycinnamate
  参考文献：
  名称：

  钌（II）催化的脱羧CH活化：通向亚烷基化芳烃的多种途径

  摘要：

  钌（II）双（羧酸盐）被证明对两种脱羧CH烯基化策略非常有效。脱羧在相当低的温度下有效地进行。脱羧钌（II）催化的独特多功能性体现在与烯烃的氧化烯化反应以及炔烃的氧化还原中性加氢芳基化反应上。

  DOI：

  10.1002/anie.201600490

文献信息

• Hydrogenolysis-free Hydrogenation by Pd Black Powder Catalyst
  作者：Shojiro Maki、Makiko Okawa、Ryo Matsui、Takashi Hirano、Haruki Niwa

  DOI：10.1055/s-2001-17485

  日期：——

  A new general method of hydrogenolysis-free hydrogenation using a commercially available Pd black powder catalyst has developed.

  一种新的通用氢化方法已经开发，采用商业化可得的Pd黑粉催化剂，无需氢解。
• Electrophilic C3−H Alkenylation of 2,6‐Dialkoxypyridine Derivatives via Pd(II)/Tl(III) Reaction System
  作者：Takahiro Yamada、Kosaku Tanaka、Yoshimitsu Hashimoto、Nobuyoshi Morita、Osamu Tamura

  DOI：10.1002/adsc.202300650

  日期：2023.9.19

  different alkene affords unsymmetrical, multi-substituted pyridine derivatives. Mechanistic studies indicate that the reaction proceeds via electrophilic thallation of heteroarenes followed by Pd-catalyzed Heck-type reaction. The utility of this method is showcased by its application to the late-stage functionalization of structurally complex bioactive molecules having 2,6-dialkoxypyridine as a core

  在此，我们报道了基于Pd(II)催化剂和Tl(OCOCF 3 ) 3的反应体系用于 2,6-二烷基吡啶与烯烃的亲电 C3−H 烯基化。Pd/硫醚配体催化系统和 Tl(III) 的协同作用可实现各种氮杂芳烃的有效 C−H 烯基化，并具有完全区域选择性。值得注意的是，使用空间位阻硫醚配体和 Pd(II)/Tl(III) 系统能够实现 2,6-二烷氧基吡啶的单选择性 C3(5)-H 烯基化，随后引入第二种不同的烯烃，得到不对称、多取代的吡啶衍生物。机理研究表明该反应通过杂芳烃的亲电铊化反应进行，随后发生 Pd 催化的 Heck 型反应。该方法的实用性通过其应用于结构复杂的生物活性分子的后期功能化来展示，该分子具有2，
• Selective Alkene Hydrogenation with Atomic Hydrogen Permeating Through a Pd Sheet Electrode
  作者：Shojiro Maki、Yasuhiro Harada、Takashi Hirano、Haruki Niwa、Yasuki Yoshida、Setsuro Ogata、Shuji Nakamatsu、Hiroshi Inoue、Chiaki Iwakura

  DOI：10.1080/00397910008087273

  日期：2000.10

  Chemoselective hydrogenation of olefinic double bonds without concomitant hydrogenolysis of allylic and benzylic C-O linkages was performed successfully by the aid of active hydrogen permeated through a Pd sheet electrode.
• Effect of solvent and hydrogen during selective hydrogenation
  作者：Shojiro Maki、Yasuhiro Harada、Ryo Matsui、Makiko Okawa、Takashi Hirano、Haruki Niwa、Megumi Koizumi、Yoshinori Nishiki、Tsuneto Furuta、Hiroshi Inoue、Chiaki Iwakura

  DOI：10.1016/s0040-4039(01)01787-7

  日期：2001.11

  Described is the solvent effect for the chemoselective hydrogenation of alkenes having a benzyloxy group (Bn-O-) using a hydrogenation system employing atomic hydrogen permeating through a Pd sheet electrode. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Novel Hypotensive Agents from <i>Verbesina </i><i>ca</i><i>racasana</i>. 6. Synthesis and Pharmacology of Caracasandiamide
  作者：Marco Carmignani、Anna R. Volpe、Franco Delle Monache、Bruno Botta、Romulo Espinal、Stella C. De Bonnevaux、Carlo De Luca、Maurizio Botta、Federico Corelli、Andrea Tafi、Giuseppe Ripanti、Giuliano Delle Monache

  DOI：10.1021/jm991004l

  日期：1999.8.1

  Caracasancliamide, a second hypotensive agent isolated from Verbesina caracasana, is the cyclobutane dimer (truxinic type) of the previously reported 1-[(3,4-dimethoxycinnamoyl)amino]-4-[(3-methyl-2-butenyl)guanidino]butane (caracasanamide) (Delle Monache, G.; et al. BioMed. Chem. Lett. 1992, 25, 415-418). The structure was confirmed by synthesis starting from beta-truxinic acid obtained by photoaddition of 3,4-dimethoxycinnamic acid. The dimer was coupled with 2 mol of prenylagmatine to give caracasandiamide in satisfactory yield. By contrast, the direct photodimerization of caracasanamide was unsuccessful. Caracasandiamide, assayed by the iv route in anesthetized rats at doses ranging from 50 to 3200 mu g/kg of body weight, was found to have! no appreciable effect on heart rate. At lower doses, the drug stimulates breathing and increases cardiac inotropism, stroke volume, and cardiac output, thus augmenting blood pressure and aortic flow. At higher doses, caracasandiamide depresses breathing likely through central neurogenic mechanisms (not involved in the cardiovascular effects), continues to stimulate cardiac inotropism, and induces, by reducing peripheral vascular resistance, arterial hypotension with reduction of both aortic flow and stroke volume. These cardiovascular effects appear to involve complex interactions at the level of the peripheral beta(1)-, beta(2)-, and alpha(2)-adrenoreceptor-dependent as well as M-2- and M-4-cholinergic receptor-dependent transductional pathways both in cardiovascular myocells and at the level of the postganglionic sympathetic endings (with reserpine- and guanethidine-like mechanisms). The cardiovascular effects of caracasandiamide, different from those of caracasanamide, do not depend, on significant actions on the central nervous system and on baroreflex path-ways. In a similar manner and more effective than caracasanamide, caracasandiamide may be considered a hypotensive and antihypertensive drug. It is devoid of some of the negative side effects, e.g., reflex tachycardia and decreased cardiac inotropism, which are shown by the majority of the most common antihypertensive and vasodilator drugs.