2-(3-methoxybenzyl)acrylaldehyde | 1262516-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-methoxybenzyl)acrylaldehyde
• 英文别名: 2-[(3-Methoxyphenyl)methyl]prop-2-enal
• CAS: 1262516-78-8
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: MOFGMFGLOSPALJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-methoxybenzyl)acrylaldehyde 在 葡萄糖 、 水 作用下， 反应 48.0h， 以19%的产率得到(R)-2-methyl-3-(3-methoxy-phenyl)propan-1-ol
  参考文献：
  名称：

  On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

  摘要：

  The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes. as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.02.003
• 作为产物：
  描述：

  2-(3-methoxybenzyl)prop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到2-(3-methoxybenzyl)acrylaldehyde
  参考文献：
  名称：

  On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

  摘要：

  The Baker's Yeast (BY) reduction of (Z)-2-chloromethyl-3-arylacrylaldehydes was found to afford (R)-2-methyl-3-aryl-propanols showing high enantiomeric excess values. Deuterium incorporation experiments were performed, in order to investigate the mechanism of the bioreduction: the formation of the corresponding substituted 2-benzylacrylaldehydes. as intermediates to be effectively reduced by Baker's Yeast, was suggested. These intermediates were synthesized and submitted to BY reduction to afford the corresponding saturated (R)-alcohols, thus confirming the conclusions drawn from labelling experiments. The enantioselectivity of their bioreduction was found to be opposite with respect to that observed for the corresponding regioisomeric 2-methylcinnamaldehydes. The preparation of the two enantiomers of 2-methyl-3-aryl-propanols by fermentation of two regioisomers represents an interesting example of substrate-controlled enantioselective reaction. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.02.003

文献信息

• Chiral Primary Amine Catalyzed Asymmetric Epoxidation of α-Substituted Acroleins
  作者：Jiuyuan Li、Niankai Fu、Long Zhang、Pengxin Zhou、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/ejoc.201001117

  日期：2010.12

  substrates in asymmetric epoxidation reactions. In this study, chiral primary amines are shown to catalyze the asymmetric epoxidation of α-substituted acroleins, a versatile type of 1,1-disubstituted terminal alkene. Among various chiral primary amines explored, the chiral primary-tertiary vicinal diamine derived from trans-1,2-diphenylethane-1,2-diamine is identified as the optimal catalyst, which, in combination

  1,1-二取代末端烯烃在不对称环氧化反应中仍然是具有挑战性的底物。在这项研究中，手性伯胺被证明可以催化 α-取代丙烯醛的不对称环氧化，这是一种多功能的 1,1-二取代末端烯烃。在探索的各种手性伯胺中，衍生自反式-1,2-二苯基乙烷-1,2-二胺的手性伯-叔邻二胺被确定为最佳催化剂，其与5-磺基水杨酸（5-SSA）结合使用, 表现出良好的催化活性（高达 95% 的产率）和对映选择性（高达 88% ee）。发现 2 M 氯化钠水溶液是最佳反应介质。
• Chiral Primary Amine-Catalyzed Divergent Coupling of α-Substituted Acrylaldehydes with α-Diazoesters
  作者：Zaikun Xue、Yao Li、Sanzhong Luo

  DOI：10.1021/acscatal.0c02405

  日期：2020.10.2

  We report, herein, aminocatalytic coupling of α-substituted acrylaldehydes with α-diazoesters, leading to chemoselective C–H insertion or cyclopropanation depending on α-substituents of diazoesters. A chiral primary–secondary diamine catalyst derived from l-tert-leucine enabled the efficient promotion of both C–H insertion and cyclopropanation pathways in good yields and high enantioselectivities at

  我们在此报告，α-取代的丙烯醛与α-重氮酯的氨基催化偶联，取决于重氮酸酯的α-取代基，导致化学选择性的C–H插入或环丙烷化。衍生自手性初级仲二胺催化剂升-叔-亮氨启用有效促进良好产率，并在室温高对映选择性两者C-H插入和环丙烷途径没有任何金属或路易斯酸助催化剂。机理研究发现了亚硝酸根离子介导的1,3-偶极环加成途径，其中重氮碳的电子性质决定了该氨基催化循环中的化学选择性。