(S)-N-(2-methoxybenzylidene)-α-methylbenzylamine | 103958-29-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-N-(2-methoxybenzylidene)-α-methylbenzylamine
• 英文别名: (S)-N-(2-methoxybenzylidene)-1-phenylethanamine；1-(2-methoxyphenyl)-N-[(1S)-1-phenylethyl]methanimine
• CAS: 103958-29-8
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: ZZDLXOXXHLYGBV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 邻甲氧基苯甲醛 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (S)-N-(2-methoxybenzylidene)-α-methylbenzylamine
  参考文献：
  名称：

  An Efficient Microwave Method for the Synthesis of Imines

  摘要：

  通过使用微波辐照和少量分子筛，可以简单、高效、干净地生成大量芳基和杂环手性和非手性亚胺。反应迅速，几分钟内即可完成，而且可以定量，大大减少了化合物分离和纯化所需的时间和溶剂用量。

  DOI：

  10.1071/ch14659
• 作为试剂：
  描述：

  硝基甲烷 、 邻甲氧基苯甲醛 在 (S)-N-(2-methoxybenzylidene)-α-methylbenzylamine 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 (1S)-1-(2-methoxyphenyl)-2-nitroethanol 、 (1R)-1-(2-甲氧基苯基)-2-硝基乙醇
  参考文献：
  名称：

  Heterogeneous Chiral Copper Complexes of Amino Alcohol for Asymmetric Nitroaldol Reaction

  摘要：

  Chiral amino alcohols supported on mesoporous silicas were synthesized and evaluated as a new class of chiral ligands in copper-catalyzed nitroaldol reaction under heterogeneous and mild reaction conditions. The activity and enantioselectivity of the present catalytic system is immensely influenced by the presence of achiral and chiral bases as an additive. The heterogenized chiral copper(II) complex of amino alcohol was found to be an effective recyclable catalyst for the nitroaldol reaction of different aldehydes such as aromatic, aliphatic, alicyclic, and alpha-beta unsaturated aldehydes to produce nitroaldol products with remarkably high enantioselectivity (>= 99%) and yields.

  DOI：

  10.1021/jo1010679

文献信息

• Highly Enantioselective Syntheses of Chiral β-Amino Alcohols in the Presence of Chiral TiIV Schiff Base Complexes as Catalysts
  作者：Rukhsana I. Kureshy、K. Jeya Prathap、Santosh Agrawal、Noor-ul H. Khan、Sayed H. R. Abdi、Raksh V. Jasra

  DOI：10.1002/ejoc.200800099

  日期：2008.6

  3′-dimethyl-5,5′-methylenebis(salicylaldehyde) with (1R,2S)-(–)-2-aminodiphenylethanol and were characterized by elemental analysis, 1H NMR, 13C NMR, IR, UV/Vis, and CD spectroscopy, optical rotation, and mass spectrometry. Highly enantioselective ring opening reactions of meso-stilbene oxide, cyclohexene oxide, cyclooctene oxide, and cis-butene oxide with anilines in the presence of several additives were carried

  通过3,3'-二叔丁基-5,5'-亚甲基双(水杨醛)和3,3'-二甲基-5,5'-亚甲基双(水杨醛)缩合制备了两种新的手性席夫碱1和2用 (1R,2S)-(-)-2-氨基二苯乙醇进行表征，并通过元素分析、1H NMR、13C NMR、IR、UV/Vis 和 CD 光谱、旋光度和质谱进行表征。在通过 Ti(OiPr) 相互作用原位生成的 TiIV 配合物的存在下，在几种添加剂的存在下进行了内消旋二苯乙烯氧化物、环己烯氧化物、环辛烯氧化物和顺丁烯氧化物与苯胺的高度对映选择性开环反应4 与手性希夫碱 1 和 2 在 0 °C 下。当手性亚胺用作添加剂时，在 10 小时内实现了具有高对映选择性（ee，> 99 %）的手性 β-氨基醇的优异产率（> 99 %）。就环氧化物开环反应生成高光学纯度手性β-氨基醇的反应性和对映选择性而言，催化剂1-Ti(OiPr)4比催化剂2-Ti(OiPr)4更好。本研
• Heterogeneous Chiral Copper Complexes of Amino Alcohol for Asymmetric Nitroaldol Reaction
  作者：Vishal J. Mayani、Sayed H. R. Abdi、Rukhsana I. Kureshy、Noor-ul H. Khan、Anjan Das、Hari C. Bajaj

  DOI：10.1021/jo1010679

  日期：2010.9.17

  Chiral amino alcohols supported on mesoporous silicas were synthesized and evaluated as a new class of chiral ligands in copper-catalyzed nitroaldol reaction under heterogeneous and mild reaction conditions. The activity and enantioselectivity of the present catalytic system is immensely influenced by the presence of achiral and chiral bases as an additive. The heterogenized chiral copper(II) complex of amino alcohol was found to be an effective recyclable catalyst for the nitroaldol reaction of different aldehydes such as aromatic, aliphatic, alicyclic, and alpha-beta unsaturated aldehydes to produce nitroaldol products with remarkably high enantioselectivity (>= 99%) and yields.
• An Efficient Microwave Method for the Synthesis of Imines
  作者：Emily C. Border、Victoria L. Blair、Philip C. Andrews

  DOI：10.1071/ch14659

  日期：——

  A large variety of aryl and heterocyclic chiral and achiral imines can be generated simply, efficiently, and cleanly through the use of microwave irradiation and the use of a small amount of molecular sieve. Reactions are rapid and complete in a matter of minutes, and can be quantitative, reducing significantly the time and amount of solvents used in compound isolation and purification.

  通过使用微波辐照和少量分子筛，可以简单、高效、干净地生成大量芳基和杂环手性和非手性亚胺。反应迅速，几分钟内即可完成，而且可以定量，大大减少了化合物分离和纯化所需的时间和溶剂用量。