S-2,6-dimethyl-N-(2-methoxy-1-methylethyl)-aniline | 118604-67-4

• 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: S-2,6-dimethyl-N-(2-methoxy-1-methylethyl)-aniline
• 英文别名: (S)-N-(1-methoxypropan-2-yl)-2,6-dimethylaniline；(S)-N-(1-methoxyprop-2-yl)-2,6-dimethylphenylamine；N-[(2S)-1-methoxypropan-2-yl]-2,6-dimethylaniline
• CAS: 118604-67-4
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: QYJCGOLBBQDWFE-NSHDSACASA-N

物化性质

• 沸点：
  301.5±30.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  S-2,6-dimethyl-N-(2-methoxy-1-methylethyl)-aniline 、 氯乙酰氯 在 吡啶 、 sodium chloride 作用下， 以 水 、 甲苯 为溶剂， 生成 S(-)-N-(1'methyl-2'-methoxyethyl)-N-chloroacetyl-2,6-dimethylaniline
  参考文献：
  名称：

  PROCESS FOR THE HYDROGENATION OF IMINES

  摘要：

  公开号：

  EP0691949B1
• 作为产物：
  描述：

  (Z)-2,6-dimethylphenyl-1'-methyl-2'-methoxyethyl-imine 在 2 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 30.0 ℃ 、4.0 MPa 条件下， 生成 (R)-N-(1-methyl-2-methoxyethyl)-2,6-dimethylaniline 、 S-2,6-dimethyl-N-(2-methoxy-1-methylethyl)-aniline
  参考文献：
  名称：

  亚胺催化对映选择性氢化中的rac- diop铱配合物的手性中毒

  摘要：

  二聚体Ir（III）络合物[Ir（PP）HI 2 ] 2（PP =对映纯生物磷s）先前已被证明是亚胺对映选择性氢化的有效催化剂。在本研究中，我们使用rac -diop制备了类似物。在可能的二聚体，只有对μ-I的轻微偏爱2异源二聚体{物[Ir（[R ，- [R）-ddiopHI 2 ]的[Ir（小号，小号）-diopHI 2 ]}。尽管这种二聚体混合物对于亚胺的氢化是中等良好的催化剂，但没有显示出预期的对映选择性。易于获得的氨基膦次膦酸酯配体（+）-（S）-pronop，以[（S）-pronop]：[Ir] tot = 1：1的比例与该二聚体混合物产生不良的催化剂，该催化剂在100h内仅产生了很少的周转。然而，以[（S）-pronop]：[Ir] tot＝ 1∶2的比例向该二聚体混合物中添加（+）-（S）-nonop产生了亚胺的对映选择性氢化的有效催化剂。由非外消旋二重奏制备的二聚体在催化中未观察到明显的手性扩增。

  DOI：

  10.1016/s0022-328x(96)06624-7

文献信息

• Process for the preparation of secondary amines
  申请人：Celgro

  公开号：US06107521A1

  公开（公告）日：2000-08-22

  N,N-disubstituted amines in which the amino nitrogen atom is bound to the carbon atom of an aromatic ring disubstituted in the positions ortho to the carbon atom, are prepared by allowing a primary amine and a compound in which an ortho, ortho-disubstituted aromatic compound carrying a nucleofuge substituent, to react in a basic environment in the presence of a catalytic palladium(0) complex and a ligand, the ratio of palladium complex to ligand being greater than at least 1:1. A typical embodiment involves the reaction of 2-methyl-6-ethylphenyl-trifluoromethylsulfonate and (S)-1-methoxy-2-aminopropane in the presence of bis(dibenzylideneacetone)palladium, tri-tert.-butylphosphine, and sodium tert.-butoxide to yield (S)-N-(1-methoxyprop-2-yl)-2-methyl-6-ethylphenylamine.

  N,N-二取代胺，其中氨基氮原子与带有对位碳原子二取代的芳香环碳原子相连，通过在碱性环境中，让一级胺和带有可离去基团的邻、对位二取代的芳香化合物在钯(0)配合物催化剂和配体的存在下反应，钯配合物与配体的比例至少大于1:1来制备。一个典型的实施例涉及2-甲基-6-乙基苯基三氟甲磺酸盐和(S)-1-甲氧基-2-氨基丙烷在二(二苄基丙酮)钯、三叔丁基膦和叔丁醇钠的存在下反应，以产生(S)-N-(1-甲氧基丙-2-基)-2-甲基-6-乙基苯胺。
• Chiral organic catalysts for the stereoselective reduction of carbon-nitrogen double bonds for the preparation of enantiomerically enriched amines
  申请人：UNIVERSITA' DEGLI STUDI DI MILANO

  公开号：EP2065371A1

  公开（公告）日：2009-06-03

  The invention relates to compounds of general formula (I): wherein R1-R7 are as defined in the description for use as catalysts in the stereoselective reduction of imines in the presence of trichlorosilane as reducing agent.

  本发明涉及一般式(I)的化合物：其中R1-R7如描述中定义，用作催化剂，存在三氯硅烷还原剂的情况下进行亚胺的立体选择性还原。
• Chiral Lewis base promoted trichlorosilane reduction of ketimines. An enantioselective organocatalytic synthesis of chiral amines
  作者：Stefania Guizzetti、Maurizio Benaglia、Franco Cozzi、Rita Annunziata

  DOI：10.1016/j.tet.2009.06.015

  日期：2009.8

  The reduction of the carbon-nitrogen double bond is an important transformation. Here we report our studies on a family of chiral organic catalysts able to promote the stereoselective reduction of ketimines with trichlorosilane. The very cheap, metal-free catalysts were easily prepared in one step from commercially available products, namely a chiral aminoalcohol and picolinic acid derivatives. The catalyst structure was extensively modified in a study that allowed to identify an extremely active species, able to promote the reduction on a large variety of substrates with high efficiency (up to 95% ee). A three component methodology has been also developed, where the enantiomerically enriched amine was isolated after performing the reaction by mixing a ketone and an amine in the presence of trichlorosilane and the catalyst. Its synthetic potentiality was demonstrated by employing the present metal-free catalytic procedure in the preparation of (S)-metolachlor, a potent and widely used herbicide. (C) 2009 Elsevier Ltd. All rights reserved.
• Spindler, Felix; Pugin, Benoit; Blaser, Hans-Ulrich, Angewandte Chemie, 1990, vol. 102, # 5, p. 561 - 562
  作者：Spindler, Felix、Pugin, Benoit、Blaser, Hans-Ulrich

  DOI：——

  日期：——
• Asymmetric hydrogenation of imines catalysed by carboxylato(diphosphine)iridium(III) complexes
  作者：Rafaël Sablong、John A Osborn

  DOI：10.1016/0957-4166(96)00397-7

  日期：1996.11

  The synthesis of three new families of monomeric carboxylato(diphosphine)iridium(III) complexes is described (e.g. diphosphine = diop, binap, bdpp). Some of these complexes catalyse the asymmetric hydrogenation of prochiral imines to amines in good activity and enantioselectivity. Copyright (C) 1996 Elsevier Science Ltd