cis-3-methylcinnamic acid | 16642-82-3

• 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: cis-3-methylcinnamic acid
• 英文别名: (Z)-3-(m-tolyl)acrylic acid；cis-m-Methyl-zimtsaeure；3-Methyl-cis-zimtsaeure；cis-3-Methylzimtsaeure；(2Z)-3-(3-Methylphenyl)-2-propenoic acid；(Z)-3-(3-methylphenyl)prop-2-enoic acid
• CAS: 16642-82-3
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: JZINNAKNHHQBOS-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-3-methylcinnamic acid 、 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 氢气 以 甲醇 为溶剂， 反应 70.0h， 以to provide 0.32 g of 3-phenylbutyric acid的产率得到(+/-)-3-苯基丁酸
  参考文献：
  名称：

  Process for producing optically active carboxylic acid

  摘要：

  本发明涉及一种制备光学活性羧酸的方法，该羧酸由式(I)表示：##STR1##其中R.sup.1、R.sup.2和R.sup.3分别表示氢原子、烷基、烯基、苯基或萘基，这些基团可以有取代基，但要求R.sup.1、R.sup.2和R.sup.3中的所有基团不同时为氢原子；当R.sup.1和R.sup.2同时为氢原子时，R.sup.3不是甲基基团；当R.sup.3为氢原子时，R.sup.1和R.sup.2均为非氢基团。该方法包括在钌-光学活性膦配合物催化剂的存在下不对称氢化式(II)表示的α，β-不饱和羧酸：##STR2##其中R.sup.1、R.sup.2和R.sup.3与上述定义相同。根据本发明的方法，所需的光学活性羧酸可以被工业上优越地生产，这些羧酸可以广泛用作合成各种有用化合物的原材料，例如合成天然物质的生理活性物质的中间体以及液晶材料。

  公开号：

  US04962230A1
• 作为产物：
  描述：

  3-甲基苯甲醛 在 水 、 苄基三甲基氢氧化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 cis-3-methylcinnamic acid
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013

文献信息

• Catalytic production of optically active carboxylic acid
  申请人：Takasago International Corporation

  公开号：EP0272787A2

  公开（公告）日：1988-06-29

  A carboxylic acid having optically active C atom, of formula: wherein R1, R2 and R3 each represents hydrogen, alkyl, alkenyl, or phenyl or naphthyl which may have a substituent, provided that all of R1 to R3 are not simultaneously hydrogen; when R1 and R2 are both hydrogen then R3 is not methyl and when R3 is hydrogen, R1 and R2 are each other than hydrogen, is produced by dissolving an a,β-unsaturated carboxylic acid represented by the formula: in an aprotic solvent, optionally adding equimolar tertiary amine and adding a ruthenium-optically active phosphine complex as a catalyst, hydrogenating under pressure of 4-135 kg/cm2, and distilling off the solvent. Three classes of such catalyst, containing a 'BINAP' group, are shown, and syntheses thereof. The carboxylic acids produced can be used as raw materials for syntheses, e.g. of physiologically active substances of natural materials, and also as liquid crystal materials.

  具有光学活性 C 原子的羧酸，其式如下 式中 R1、R2 和 R3 分别代表氢、烷基、烯基或苯基或萘基，它们可以有一个取代基，但 R1 至 R3 不能同时为氢；当 R1 和 R2 都为氢时，R3 不是甲基，当 R3 为氢时，R1 和 R2 不是氢： 将 a，β-不饱和羧酸溶解于非烷基溶剂中，选择性地加入等摩尔叔胺，并加入钌-光活性膦络合物作为催化剂，在 4-135 kg/cm2 的压力下进行氢化，然后蒸馏掉溶剂。 图中展示了三类含有 "BINAP "基团的催化剂及其合成方法。 生成的羧酸可用作合成原料，如天然材料中的生理活性物质，也可用作液晶材料。
• Templating Photodimerization of <i>trans</i>-Cinnamic Acids with Cucurbit[8]uril and γ-Cyclodextrin
  作者：Mahesh Pattabiraman、Arunkumar Natarajan、Lakshmi S. Kaanumalle、V. Ramamurthy

  DOI：10.1021/ol047866k

  日期：2005.2.1

  Cucurbit[8]uril and gamma-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with transcinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.
• US4962230A
  申请人：——

  公开号：US4962230A

  公开（公告）日：1990-10-09
• Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors
  作者：Keisuke Nishikawa、Hiroshi Fukuda、Masato Abe、Kazunari Nakanishi、Tomoya Taniguchi、Takashi Nomura、Chihiro Yamaguchi、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2013.08.013

  日期：2013.12

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.
• Process for producing optically active carboxylic acid
  申请人：Takasago International Corporation

  公开号：US04962230A1

  公开（公告）日：1990-10-09

  A process for producing an optically active carboxylic acid represented by formula (I): ##STR1## wherein R.sup.1, and R.sup.2, and R.sup.3 each represents a hydrogen atom, an alkyl group, an alkenyl group, or a phenyl or naphthyl group which may have a substituent, provided that all of R.sup.1, R.sup.2, and R.sup.3 are not simultaneously a hydrogen atom; when R.sup.1 and R.sup.2 are simultaneously a hydrogen atom, then R.sup.3 is not a methyl group; and that when R.sup.3 is a hydrogen atom, then R.sup.1 and R.sup.2 are each a group other then a hydrogen atom, is disclosed, comprising asymmetrically hydrogenating an .alpha.,.beta.-unsaturated carboxylic acid represented by formula (II): ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 are the same as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. According to the process of the invention, the desired optically active carboxylic acids which can be widely used as raw materials for synthesizing various useful compounds, for example, as intermediates for synthesizing physiologically active substances of natural materials and also as liquid crystal materials can be industrially advantageously produced.

  本发明涉及一种制备光学活性羧酸的方法，该羧酸由式(I)表示：##STR1##其中R.sup.1、R.sup.2和R.sup.3分别表示氢原子、烷基、烯基、苯基或萘基，这些基团可以有取代基，但要求R.sup.1、R.sup.2和R.sup.3中的所有基团不同时为氢原子；当R.sup.1和R.sup.2同时为氢原子时，R.sup.3不是甲基基团；当R.sup.3为氢原子时，R.sup.1和R.sup.2均为非氢基团。该方法包括在钌-光学活性膦配合物催化剂的存在下不对称氢化式(II)表示的α，β-不饱和羧酸：##STR2##其中R.sup.1、R.sup.2和R.sup.3与上述定义相同。根据本发明的方法，所需的光学活性羧酸可以被工业上优越地生产，这些羧酸可以广泛用作合成各种有用化合物的原材料，例如合成天然物质的生理活性物质的中间体以及液晶材料。