2-(Methoxymethyl)-3-phenyl-2-propenoic acid | 164738-69-6

• 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: 2-(Methoxymethyl)-3-phenyl-2-propenoic acid
• 英文别名: (E)-2-(methoxymethyl)-3-phenylacrylic acid；(E)-2-(methoxymethyl)-3-phenylprop-2-enoic acid
• CAS: 164738-69-6
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: ZFEHFVNETXEWFA-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(Methoxymethyl)-3-phenyl-2-propenoic acid 在 氯化亚砜 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  酰胺的α-手性中心的高对映建设通过α的铱催化加氢，β -不饱和酰胺

  摘要：

  Abstractmagnified imageThe chiral center at the α‐position of amides is installed in excellent enantioselectivity via the iridium‐catalyzed asymmetric hydrogenation of α,β‐unsaturated amides under mild conditions. Even aliphatic amides are suitable substrates. The presence of a hydrogen atom on the nitrogen of the amide is important for the enantioselectivity of the reaction.

  DOI：

  10.1002/adsc.200900080
• 作为产物：
  描述：

  (E)-methyl 2-(methoxymethyl)-3-phenylacrylate 在 甲醇 、 potassium hydroxide 作用下， 生成 2-(Methoxymethyl)-3-phenyl-2-propenoic acid
  参考文献：
  名称：

  酰胺的α-手性中心的高对映建设通过α的铱催化加氢，β -不饱和酰胺

  摘要：

  Abstractmagnified imageThe chiral center at the α‐position of amides is installed in excellent enantioselectivity via the iridium‐catalyzed asymmetric hydrogenation of α,β‐unsaturated amides under mild conditions. Even aliphatic amides are suitable substrates. The presence of a hydrogen atom on the nitrogen of the amide is important for the enantioselectivity of the reaction.

  DOI：

  10.1002/adsc.200900080

文献信息

• Synthesis of Chiral<i>α</i>-Benzyl-<i>β</i>²-hydroxy Carboxylic Acids through Iridium-Catalyzed Asymmetric Hydrogenation of<i>α</i>-Oxymethylcinnamic Acids
  作者：Ze-Yu Li、Song Song、Shou-Fei Zhu、Na Guo、Li-Xin Wang、Qi-Lin Zhou

  DOI：10.1002/cjoc.201400361

  日期：2014.8

  An asymmetric hydrogenation of α‐oxymethylcinnamic acids was developed by using chiral spiro phosphine‐oxazoline/iridium complexes as catalysts to prepare β2‐hydroxycarboxylic acids with high reactivity (TON up to 2000) and excellent enantioselectivity (up to 99.5% ee). By using this highly efficient asymmetric hydrogenation as a key step, a concise total synthesis of natural product homoisoflavone

  的不对称氢化α -oxymethylcinnamic酸通过使用手性开发螺膦-恶唑啉/铱络合物作为催化剂，以制备β 2个羟基羧酸具有高反应性（TON高达2000）和对映选择性优良（高达99.5％ee值）。通过使用这种高效的不对称氢化作为关键步骤，完成了天然产物高异黄酮（S）-（+）- 4的简明全合成。
• 2-(Methoxymethyl)--3-aryl-2-propenoic Acids and 2-(Bromomethyl)-3-aryl-2-propenoic Acids from Aromatic Aldehydes
  作者：Engelbert Ciganek

  DOI：10.1021/jo00119a047

  日期：1995.7
• First asymmetric synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine
  作者：Matthias Breuning、David Hein

  DOI：10.1016/j.tetasy.2007.06.010

  日期：2007.7

  The enantioselective synthesis of a Q-symmetric 2-endo,6-endo-disubstituted bispidine (3,7-diazabicyclo[3.3.1]nonane) has been accomplished for the first time. The key step was a Michael addition of the protected beta-amino ester methyl (R)-3-N-benzyl-N[(S)-1-phenylethyl]amino}-3-phenylpropionate to its alpha-methylene derivative delivering an anti,anti-configured alpha,alpha'-methylene-bridged bis(beta-amino ester) as the major diastereomer. Deprotection, reduction and cyclisation furnished (1R,2R,5R,6R)-2,6-diphenyl-3,7-bis(S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane in six steps and 15% overall yield. (c) 2007 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Construction of the α-Chiral Center of Amides<i>via</i>Iridium-Catalyzed Hydrogenation of α,β-Unsaturated Amides
  作者：Wei-Jing Lu、Xue-Long Hou

  DOI：10.1002/adsc.200900080

  日期：2009.6

  Abstractmagnified imageThe chiral center at the α‐position of amides is installed in excellent enantioselectivity via the iridium‐catalyzed asymmetric hydrogenation of α,β‐unsaturated amides under mild conditions. Even aliphatic amides are suitable substrates. The presence of a hydrogen atom on the nitrogen of the amide is important for the enantioselectivity of the reaction.