阿魏酸甲酯 | 97966-29-5

• 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
• 中文名称: 阿魏酸甲酯
• 中文别名: (E)-3'-羟基-4'-甲氧基肉桂酸甲酯
• 英文名称: methyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate
• 英文别名: (E)-methyl 3-(3-hydroxy-4-methoxyphenyl)acrylate；methyl isoferulate；methyl (E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate
• CAS: 97966-29-5
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: JTLOUXXZZFFBBW-GQCTYLIASA-N

物化性质

• 熔点：
  119-120℃
• 沸点：
  370℃
• 密度：
  1.204
• 闪点：
  145℃
• 溶解度：
  DCM、DMF、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  阿魏酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 12.5h， 生成 异阿魏酸
  参考文献：
  名称：

  Very Short and Efficient Syntheses of the Spermine Alkaloid Kukoamine A and Analogs Using Isolable Succinimidyl Cinnamates

  摘要：

  摘要 用多种可分离的琥珀酰亚胺基肉桂酸酯对精胺和亚精胺的初级氨基功能进行直接选择性酰化，然后进行催化氢化反应，可获得高产率的精胺生物碱 Kukoamine A 和适合结构-活性关系研究的类似物。通过芳香醛与酰化物 Ph3P=CRCO2Me 的 Wittig 反应，然后在 N,N′-二环己基碳二亚胺存在下用 N-hydroxysuccinimide 进行皂化和活化，很容易获得合适的琥珀酰亚胺肉桂酸盐。

  DOI：

  10.1246/cl.2005.264
• 作为产物：
  描述：

  异阿魏酸 在 碘 、 zinc trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 4.17h， 生成 阿魏酸甲酯
  参考文献：
  名称：

  Zn(OTf)₂-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids

  摘要：

  Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I-2, and a catalytic amount of Zn(OTf)(2). Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from trans-esterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.

  DOI：

  10.1021/jo302502r

文献信息

• [EN] HYDROXAMID ACID DERIVATIVES AS HISTONE DEACETYLASE (HDAC) INHIBITORS<br/>[FR] DERIVES D'ACIDE HYDROXAMIQUE UTILISES COMME INHIBITEURS DE L'HISTONE DESACETYLASE (HDAC)
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2004063169A1

  公开（公告）日：2004-07-29

  A compound having the following formula (I): wherein R1 is N-containing heterocyclic ring optionally substituted with one or more suitable substituent(s), R2 is hydroxyamino, R3 is hydrogen or a suitable substituent, L1 is -(CH?2#191)?n#191- (wherein n is an integer of 0 to 6) optionally substituted with one or more suitable substituent(s), wherein one or more methylene(s) may be replaced with suitable heteroatom(s), and L2 is lower alkenylene, or a salt thereof. The compound is useful as a histone deacetylase inhibitor.

  具有以下化学式（I）的化合物：其中R1是N-含杂环环，可选择地取代一个或多个适当的取代基，R2是羟胺基，R3是氢或适当的取代基，L1是-(CH?2#191)?n#191-（其中n是0到6的整数），可选择地取代一个或多个适当的取代基，其中一个或多个亚甲基可以被适当的杂原子取代，L2是较低的烯烃基，或其盐。该化合物可用作组蛋白去乙酰化酶抑制剂。
• Compound and use of the same as medicine
  申请人：Tsumura & Co.

  公开号：US05344845A1

  公开（公告）日：1994-09-06

  Disclosed herein is a specific cinnamic acid derivative such as methyl 4-(4-acetoxy-3-methoxycinnamanide)-1-cyclohexanecarboxylate, or a pharmaceutically acceptable salt thereof. These compounds are useful as IV-type allergic reaction-suppressive drugs.

  本文披露了一种特定的肉桂酸衍生物，例如甲基4-(4-乙酰氧基-3-甲氧基肉桂酰胺基)-1-环己烷羧酸酯，或其药用可接受的盐。这些化合物可用作IV型过敏反应抑制药物。
• CONVENIENT MICROWAVE ASSISTED SYNTHESIS OF NATURALLY OCCURRING METHYL (<i>E</i>)-CINNAMATES
  作者：Rajesh P. Mahajan、Shamkant L. Patil、Raghao S. Mali

  DOI：10.1080/00304940509354962

  日期：2005.6

  ASSISTED SYNTHESIS OF NATURALLY OCCUR-RING METHYL (E)-CINNAMATESSubmitted by Rajesh P. Mahajan, Shamkant L. Patil* and Raghao S. Mali*(12/15/04)School of Chemical Sciences, North Maharashtra UniversityJalgaon - 425 001, INDIAe-mail: [e-mail]; Fax No. + (91) 0257 2258403A large number of methyl cinnamates have been isolated from various plant sources.Thus, the parent methyl (E)-cinnamate

  Rajesh P. Mahajan、Shamkant L. Patil* 和 Raghao S. Mali* (12/15/04) 化学科学学院，北马哈拉施特拉大学 -14J500 提交的自然发生的环甲基 (E)-肉桂的方便的微波辅助合成, 印度电子邮箱：[e-mail]；Fax No. + (91) 0257 2258403大量的肉桂酸甲酯已从各种植物来源中分离出来，从而分离出母体（E）肉桂酸甲酯（3a）
• Syntheses of Certain 3-Aryl-2-propenoates and Evaluation of their Cytotoxicity
  作者：Nguyen-Hai Nam、Young-Jae You、Yong Kim、Dong-Ho Hong、Hwan-Mook Kim、Byung Zun Ahn

  DOI：10.1016/s0960-894x(01)00165-2

  日期：2001.5

  A series of 3-aryl-2-propenoates including cinnamates, (E)-methyl/ethyl 3-[2-(1,4-dimethoxy-5,8-dione)naphthalenyl]-2-propenoates (8ba, 8bb) and (E)-methyl/ethyl 3-[2-(1,4-dihydroxy-9,10-dione)anthracenyl]-2-propenoates (9aa,9ab) was synthesized and evaluated for antitumor cytotoxicity. It was found that the ortho- or para-dihydroxy funtionality on the aryl ring was essential for the cytotoxicity of

  一系列3-芳基-2-丙烯酸酯，包括肉桂酸酯，（E）-甲基/乙基3- [2-（2-（1,4-二甲氧基-5,8-二酮）萘] -2-丙烯酸酯（8ba，8bb）和合成（E）3- [2-（1,4-二羟基-9,10-二酮）蒽基] -2-丙烯酸（9aa，9ab）-甲基/乙基（9aa，9ab），并评估其抗肿瘤细胞毒性。发现芳基环上的邻或对二羟基官能对于肉桂酸酯的细胞毒性至关重要。化合物8ba，8bb和9aa，9ab对多种肿瘤细胞系显示出强力的细胞毒性。
• Inhibitory Effects of Substituted Cinnamic Acid Esters on Mushroom Tyrosinase
  作者：Zhenghua Zhang、Jinbing Liu、Fengyan Wu、Liangzhong Zhao

  DOI：10.2174/1570180811310060009

  日期：2013.5.1

  A series of substituted cinnamic acid esters were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. Compound 8 was found to be the most potent inhibitor with IC50 value of 5.60µM. Preliminary structure activity relationships (SARs) were concluded. The inhibition kinetics analyzed by Lineweaver–Burk plots revealed that compound 8 was anti-competitive

  合成了一系列取代的肉桂酸酯，并评价了其对蘑菇酪氨酸酶双酚酶活性的抑制作用。发现化合物8是最有效的抑制剂，IC50值为5.60µM。初步的结构活动关系（SAR）总结。通过Lineweaver-Burk图分析的抑制动力学表明，化合物8是抗竞争性抑制剂。