(E)-methyl p-dimethylaminomethylcinnamate | 1017279-66-1

• 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: (E)-methyl p-dimethylaminomethylcinnamate
• 英文别名: methyl (E)-3-[4-[(dimethylamino)methyl]phenyl]prop-2-enoate
• CAS: 1017279-66-1
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: IZOSGWGVJDYNNO-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl p-dimethylaminomethylcinnamate 在 草酰氯 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 20.25h， 生成 5-[bis(tert-butoxycarbonyl)]amino-1-(chloromethyl)-3-[(E)-4-(dimethylaminomethyl)cinnamoyl]-1,2-dihydro-3H-benzo[e]indole
  参考文献：
  名称：

  Weight loss effects of quaternary salts of 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles; structure–activity relationships

  摘要：

  Quaternary salt analogues based on the DNA minor groove binder and adenine N3 alkylating agent 5-amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole (aminoCBI) show remarkable effects on the body weight of mice (a long-term failure to gain weight relative to matched controls with no loss of appetite or perceptible deterioration in health) following administration of a single (non-toxic) dose between about 0.5-5 mu mol/kg. The nature of the quaternizing group was not important, but a related hydroxyCBI analogue was much less effective. Compounds where the chloro group was replaced by a hydrogen or hydroxy group (thus abrogating DNA alkylating capability) showed no weight control activity. It is speculated, based on other studies, that the marked long-term weight control effect is due to inhibition of bile flow into the intestine and reduced absorption of triglycerides, together with accelerated cell death in spleen and white adipose tissues due to drug accumulation there. This class of compound may serve as interesting tools for further study of these phenomena. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.007

文献信息

• A Photocatalytic Regioselective Direct Hydroaminoalkylation of Aryl-Substituted Alkenes with Amines
  作者：Natalia A. Larionova、Jun Miyatake Ondozabal、Emily G. Smith、Xacobe C. Cambeiro

  DOI：10.1021/acs.orglett.1c01715

  日期：2021.7.16

  hydroaminoalkylation of cinnamate esters has been developed. The reaction involves the regioselective addition of α-aminoalkyl radicals generated from aniline derivatives or aliphatic amines to the α-position of unsaturated esters. The scope of aromatic alkenes was extended to styrenes undergoing hydroaminoalkylation with anti-Markovnikov selectivity, which confirms the importance of the aromatic group

  已经开发了一种用于肉桂酸酯的α-选择性加氢氨基烷基化的光催化方法。该反应涉及由苯胺衍生物或脂肪胺生成的 α-氨基烷基自由基与不饱和酯的 α-位的区域选择性加成。芳族烯烃的范围扩展到苯乙烯以反马尔科夫尼科夫选择性进行加氢氨基烷基化，这证实了 β 位芳族基团的重要性。在连续流动条件下证明了简单的放大，突出了该方法的实用性。
• Reduction of Electron‐Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
  作者：Natalia A. Larionova、Jun Miyatake Ondozabal、Xacobe C. Cambeiro

  DOI：10.1002/adsc.202000751

  日期：2021.1.19

  Direct hydrogen atom transfer from a photoredox‐generated Hantzsch ester radical cation to electron‐deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT‐driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective

  氢原子从光氧化还原产生的Hantzsch酯自由基阳离子直接转移到缺电子的烯烃中，使得在温和，操作简单的条件下有效的正式加氢反应得以发展。HAT驱动的机制得到了实验和计算研究的支持。该反应适用于各种肉桂酸酯衍生物和相关结构，无论芳环中是否存在给电子或吸电子取代基且具有良好的官能团相容性。
• [EN] INDOLINE DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS DE L'INDOLINE ET LEURS UTILISATIONS
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2008039087A2

  公开（公告）日：2008-04-03

  (EN) The present invention relates to compounds which are indoline derivatives of formula (I), wherein Rl, R2, R3, R4 and n are as defined in the specification, intermediates used in their synthesis and pharmaceutical compositions containing these compounds. The invention is also concerned with methods utilising these compounds in prophylactic or therapeutic treatment of obesity, weight gain, metabolic disorders resulting in obesity or weight gain and associated conditions such as high blood glucose and triglycerides, and Type II diabetes.(FR) La présente invention concerne des composés qui sont des dérivés de l'indoline, ainsi que des intermédiaires utilisés pour leur synthèse et des compositions pharmaceutiques contenant lesdits composés. L'invention concerne également des procédés utilisant ces composés dans le traitement prophylactique ou thérapeutique de l'obésité, du gain de poids, des troubles métaboliques ayant pour conséquence obésité ou gain de poids et des troubles associés tels qu'une glycémie élevée, un taux élevé de triglycérides et le diabète de type II.