3-methylbutyl (2E)-3-phenyl-2-propenoate | 85180-66-1

• 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: 3-methylbutyl (2E)-3-phenyl-2-propenoate
• 英文别名: 3-methylbutyl cinnamate；isopentyl cinnamate；isoamyl cinnamate；trans-cinnamic acid isopentyl ester；trans-Zimtsaeure-isopentylester；3-methylbutyl (E)-3-phenylprop-2-enoate
• CAS: 85180-66-1
• 化学式: C₁₄H₁₈O₂
• mdl: MFCD00026518
• 分子量: 218.296
• InChiKey: JFHCDEYLWGVZMX-CMDGGOBGSA-N

物化性质

• 熔点：
  133 °C(Solv: methanol (67-56-1))
• 沸点：
  216 °C
• 密度：
  1.006±0.06 g/cm3(Predicted)
• LogP：
  4.340 (est)
• 物理描述：
  Isoamyl cinnamate is a pale yellow liquid with iridescent sheen. (NTP, 1992)
• 闪点：
  greater than 212 °F (NTP, 1992)
• 溶解度：
  less than 1 mg/mL at 68° F (NTP, 1992)
• 折光率：
  1.533-1.541
• 保留指数：
  1717.6;1719

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 异戊醇 在 amberlyst-15 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 0.67h， 生成 3-methylbutyl (2E)-3-phenyl-2-propenoate
  参考文献：
  名称：

  An efficient chemoselective strategy for the preparation of (E)-cinnamic esters from cinnamaldehydes using heterogeneous catalyst and DDQ

  摘要：

  An efficient chemoselective protocol is developed for the synthesis of (E)-cinnamic esters from substituted cinnamaldehydes or cinnamyl alcohols using a combination of DDQ and heterogeneous catalyst under microwave irradiation. The method showed remarkable selectivity for cinnamaldehydes over aliphatic and aromatic aldehydes, which is a novel finding. The results demonstrate that the developed protocol can be a useful synthetic tool for chemoselective esterification in total synthesis of complex organic compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.011

文献信息

• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• Kinetics of trans-Cinnamic Anhydride Reactions Catalyzed by Pyridine, 4-Dimethylaminopyridine, and N-Methylimidazole
  作者：Shu-Fen Lin、Kenneth A. Connorsx

  DOI：10.1002/jps.2600700302

  日期：1981.3

  pyridine, 4-dimethylaminopyridine, and N-methylimidazole as catalysts. The absolute rates of the catalyzed hydrolysis decreased with increasing acetonitrile content (decreasing solvent polarity), but the catalytic efficiency of N-methylimidazole and 4-dimethylaminopyridine relative to pyridine increased as the solvent polarity decreased. The relative catalytic rates for the cinnamoylation of n-propanol

  在吡啶，4-二甲基氨基吡啶和N-甲基咪唑作为催化剂的存在下，研究了反式肉桂酸酐的水解动力学及其与羟基化合物的反应动力学。随着乙腈含量的增加（降低的溶剂极性），催化水解的绝对速率降低，但随着溶剂极性的降低，N-甲基咪唑和4-二甲基氨基吡啶相对于吡啶的催化效率提高。吡啶，N-甲基咪唑和4-二甲基氨基吡啶的正丙醇在乙腈中肉桂酸的相对催化速率分别为1：259：16,000。
• Design, Synthesis, and Preliminary Evaluation of Substituted Cinnamic Acid Esters as Selective Matrix Metalloproteinase Inhibitors
  作者：Zhi-Hao Shi、Nian-Guang Li、Qian-Ping Shi、Hao-Tang、Yu-Ping Tang

  DOI：10.1002/ddr.21015

  日期：2012.9

  Strategy, Management and Health Policy Preclinical Research

  战略，管理与卫生政策 临床前研究
• Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations
  作者：Balasubramanian Narasimhan、Deepak Belsare、Devayani Pharande、Vishnukant Mourya、Avinash Dhake

  DOI：10.1016/j.ejmech.2004.06.013

  日期：2004.10

  A series of esters (I(a-k)), substituted derivatives (II(a-d)) and amides (III(a-q)) of cinnamic acid were synthesized and evaluated as antibacterial and antifungal agents. All the derivatives belonging to the series I, II and III showed antimicrobial activity comparable to the standard. Compounds I(f) and II(c) proved to be the most effective compounds. Quantitative structure-activity relationship

  合成了肉桂酸的一系列酯（I（ak）），取代的衍生物（II（ad））和酰胺（III（aq）），并将其作为抗菌剂和抗真菌剂进行了评估。属于系列I，II和III的所有衍生物均显示出与标准品相当的抗菌活性。化合物I（f）和II（c）被证明是最有效的化合物。利用多元线性回归分析进行定量构效关系（QSAR）研究，以发现化合物的不同计算理化参数与生物活性之间的相关性。肉桂酸衍生物I（ak），II（ad）和III（aq）的结构特征及其抗菌活性的定量模型表明，革兰氏阴性大肠杆菌和白色念珠菌（真菌）是最敏感的微生物。
• [EN] COSMETIC USE OF PIPERIDINE DERIVATIVES<br/>[FR] UTILISATION COSMETIQUE DE DERIVES DE LA PIPERIDINE
  申请人：OREAL

  公开号：WO2005123678A1

  公开（公告）日：2005-12-29

  The present invention relates to the cosmetic use, as an agent for combating wrinkles, especially expression wrinkles, and/or for decontracting the skin and/or relaxing the features, of at least one piperidine derivative chosen from the compounds of formula (I) and the salts and optical isomers thereof. The invention also relates to novel piperidine der vatives, and also to cosmetic compositions containing them.

  本发明涉及一种化妆品用途，作为一种用于对抗皱纹，特别是表情皱纹，并/或用于舒缓皮肤和/或放松面部的剂，所述剂至少包括从式(I)化合物中选择的哌啶衍生物及其盐和光学异构体。该发明还涉及新型哌啶衍生物，以及含有它们的化妆品组合物。

表征谱图