(2E)-2-[(4-methoxyphenyl)methylidene]-3,3-dimethylbutanoic acid | 924264-87-9

• 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: (2E)-2-[(4-methoxyphenyl)methylidene]-3,3-dimethylbutanoic acid
• CAS: 924264-87-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: JLOSKGDTHGUSNJ-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-2-[(4-methoxyphenyl)methylidene]-3,3-dimethylbutanoic acid 在 5%-palladium/activated carbon 、 氢气 、 辛可尼丁 、 苄胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 生成 2-[(4-methoxyphenyl)methyl]-3,3-dimethylbutanoic acid 、 (S)-2-(4-methoxybenzyl)-3,3-dimethylbutanoic acid
  参考文献：
  名称：

  Structural requirements for substrate in highly enantioselective hydrogenation over the cinchonidine-modified Pd/C

  摘要：

  Relationship between substrate Structure and enantioselectivity is studied for the asymmetric hydrogenation of 42 different (E)-alpha, beta-disubstituted acrylic acids (propenoic acids) over cinchonidine-modified Pd/C. The beta-phenyl group is indispensable for high enantioselectivity of alpha-phenylcinnamic acid (2,3-diphenylpropenoic acid, 81% ee), and substitution on this group affects markedly the selectivity. The high ee up to 92% was achieved by the beta-p-alkoxyphenyl substitution, and the selectivity is ascribed mainly to stronger interaction of the substrate with the chiral modifier on the catalyst surface. In contrast, substitution on the alpha-phenyl group does not affect notably the enantioselectivity (80-82% ee) or even the alpha-phenyl group itself is not indispensable but replaceable with a properly bulky group for the high enantioselectivity, (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2008.11.022
• 作为产物：
  描述：

  二氧化碳 、 1-(3,3-二甲基-1-丁炔基)-4-甲氧基苯 在 二氯二茂钛 、 magnesium,2-methylpropane,bromide 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以46%的产率得到(E)-2-(4-methoxyphenyl)-4,4-dimethylpent-2-enoic acid
  参考文献：
  名称：

  Cp 2 TiCl 2催化炔烃与CO 2的加氢羧化反应：形成α，β-不饱和羧酸†

  摘要：

  已经报道了Cp 2 TiCl 2催化炔烃与CO 2（大气压）的加氢羧化。一系列炔烃以高收率和高区域选择性被转化为相应的α，β-不饱和羧酸。反应进行加氢钛化，金属转移和随后用CO 2羧化。

  DOI：

  10.1039/c6ra25003c

文献信息

• METHOD FOR MANUFACTURING A BETA-DIARYL ELECTRON WITHDRAWING GROUP SUBSTITUTED COMPOUND
  申请人：Miyaura Norio

  公开号：US20100121069A1

  公开（公告）日：2010-05-13

  An electron withdrawing group substituted β-arylolefin derivative represented by general formula (I) (in the formula, Ar 1 represents an aryl group, E represents a formyl, acyl and so on) is allowed to react with an arylboronic acid represented by general formula (II) Ar 2 —BX m M n in the general formula (IV) RhY o L 1 p (Chiraphos) q (in the formula, Y represents ClO 4 , BF 4 , PF 6 , SbF 6 , OTf, halogen atom, hydroxyl group, alkoxy group or acyloxy group, L 1 represents an organic ligand) to produce an optically active β-diaryl electron withdrawing group substituted compound represented by general formula (V)