2-dimethylamino-1-phenyl-ethanone; hydrochloride | 61185-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-dimethylamino-1-phenyl-ethanone; hydrochloride
• 英文别名: 2-Dimethylamino-1-phenyl-aethanon; Hydrochlorid；2-(Dimethylamino)-1-phenylethan-1-one hydrochloride；2-(dimethylamino)-1-phenylethanone;hydrochloride
• CAS: 61185-97-5
• 化学式: C₁₀H₁₃NO*ClH
• 分子量: 199.68
• InChiKey: ADBMYWFNCZQNCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-dimethylamino-1-phenyl-ethanone; hydrochloride 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 chiral Cr(CO)3 complexed diphosphane 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、5.0 MPa 条件下， 反应 18.0h， 生成 (S)-2-二甲基氨基-1-苯基乙醇
  参考文献：
  名称：

  Chiral tricarbonyl(η 6 -arene)chromium complexed diphosphanes. Highly enantioselective rhodium-mediated hydrogenation of ketones

  摘要：

  Arenechromium complexed diastereomeric aminophosphine-phosphinite ligands derived from tetrahydroisoquinoline have been synthesised and examined as chiral auxiliaries in the hydrogenation of functionalised ketones. A cyclopentyl-substituted anti-stereoisomer is providing the highest enantioselectivities (up to > 99% ee). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00325-2

文献信息

• Asymmetric Hydrogenation of α, β, and γ-Aminoketones Catalyzed by Cationic Rhodium(I){AMPP} Complexes
  作者：Marc Devocelle、Francine Agbossou、André Mortreux

  DOI：10.1055/s-1997-1004

  日期：1997.11

  The chiral cationic rhodium aminophosphine-phosphinite complexes 4-6 were applied successfully in the asymmetric hydrogenation of α- (7-9), β- (10, 11) and γ- (12) aminoketone hydrochloride derivatives leading to the corresponding aminoalcohols in up to 97, 93, and 92 % enantiomeric excesses for the three types of substrates respectively.

  手性阳离子铑氨基膦-膦配合物 4-6 成功地应用于 δ- (7-9)、δ- (10, 11) 和 δ³- (12) 氨基酮盐酸盐衍生物的不对称氢化反应，得到相应的氨基醇，三种底物的对映体过量率分别高达 97%、93% 和 92%。
• Synthesis and application in enantioselective hydrogenation of new free and chromium complexed aminophosphine–phosphinite ligands
  作者：Corinne Pasquier、Said Naili、Lydie Pelinski、Jacques Brocard、André Mortreux、Francine Agbossou

  DOI：10.1016/s0957-4166(97)00642-3

  日期：1998.1

  A straightforward synthesis of new free and Cr(CO)(3) complexed AMPP ligands (4-7) is described starting from (S)-indoline-2-carboxylic acid. The ligands were applied successfully in the asymmetric hydrogenation of ex-functionalized ketones i.e. a ketolactone 8, a ketoamide 9 and an aminoketone 10 leading to the corresponding optically active alcohols in 99, 97, and 99% ee respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Chiral tricarbonyl(η 6 -arene)chromium complexed diphosphanes. Highly enantioselective rhodium-mediated hydrogenation of ketones
  作者：Corinne Pasquier、Lydie Pélinski、Jacques Brocard、André Mortreux、Francine Agbossou-Niedercorn

  DOI：10.1016/s0040-4039(01)00325-2

  日期：2001.4

  Arenechromium complexed diastereomeric aminophosphine-phosphinite ligands derived from tetrahydroisoquinoline have been synthesised and examined as chiral auxiliaries in the hydrogenation of functionalised ketones. A cyclopentyl-substituted anti-stereoisomer is providing the highest enantioselectivities (up to > 99% ee). (C) 2001 Elsevier Science Ltd. All rights reserved.