(1R,2R)-2-(二甲基氨基)-1-苯基-1-丙醇 | 14222-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1R,2R)-2-(二甲基氨基)-1-苯基-1-丙醇
• 英文名称: 1R,2R-N-methylpseudoephedrine
• 英文别名: (-)-(1R,2R)-N-methylpseudoephedrine；(1R,2R)-(+)-N-methylpseudoephedrine；(1R,2R)-N-methylpseudoephedrine；(-)N-methyl-ψ-ephedrine；(1R,2R)-N-Methylpseudoephedrin；(R,R)-N-methylpseudoephedrine；(1R,2R)-2-(dimethylamino)-1-phenylpropan-1-ol
• CAS: 14222-20-9
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: FMCGSUUBYTWNDP-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-(二甲基氨基)-1-苯基-1-丙醇 在 potassium tert-butylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 叔丁醇 为溶剂， 反应 6.0h， 生成 Dimethyl-((1R,2R)-1-methyl-2-phenyl-2-propa-1,2-dienyloxy-ethyl)-amine
  参考文献：
  名称：

  An Efficient Synthesis of Enantiopure 1-Alkoxy-1,2-propadienes from Propargyl Bromide

  摘要：

  一系列对映纯功能化醇通过其相应钠醇盐与丙炔溴化物反应后，再经过t-BuOK催化的异构化反应，对得到的丙炔醚进行O-烯丙基化，获得了良好的总体产率。

  DOI：

  10.1055/s-1994-25577
• 作为产物：
  描述：

  甲胺苯丙酮 在 (+)-methylbutylmagnesium bromide 作用下， 生成 (1R,2R)-2-(二甲基氨基)-1-苯基-1-丙醇
  参考文献：
  名称：

  Influence of temperature of the stereospecific reduction of (?)-?-dimethylaminopropiophenone (methylephedrone) under the action of optically active 2-methylbutyl magnesium bromide

  摘要：

  DOI：

  10.1007/bf00854399
• 作为试剂：
  描述：

  3,3,3-三氟丙酮酸乙酯 、 三乙基铝 在 (1R,2R)-2-(二甲基氨基)-1-苯基-1-丙醇 作用下， 以 乙醚 、 正己烷 为溶剂， 以95%的产率得到ethyl (2S)-2-hydroxy-2-(trifluoromethyl)butanoate
  参考文献：
  名称：

  A Practical Synthesis of 5-Lipoxygenase Inhibitor MK-0633

  摘要：

  Practical, chromatography-free syntheses of 5-lipoxygenase inhibitor MK-0633 p-toluenesullonate (1) are described. The first route used an asymmetric zincate addition to ethyl 2,2,2-trifluoropyruvate followed by 1,3,4-oxadiazole formation and reductive amination as key steps. An improved second route features an inexpensive diastereomeric salt resolution of vinyl hydroxy-acid 22 followed by a robust end-game featuring a through-process hydrazide acylation/1,3,4-oxadiazole ring closure/salt formation sequence to afford MK-0633 p-toluenesulfonate (1).

  DOI：

  10.1021/jo100561u

文献信息

• [EN] PROCESS FOR THE SYNTHESIS OF CYCLIC CARBAMATES<br/>[FR] PROCÉDÉ DE SYNTHÈSE DE CARBAMATES CYCLIQUES
  申请人：LONZA AG

  公开号：WO2012048884A1

  公开（公告）日：2012-04-19

  The invention is directed to a process for the preparation of a cyclic carbamate starting with a chiral propargylic alcohol and/or a suitable salt thereof, which is reacted with a cyclisation agent selected from phosgene, diphosgene, triphosgene and mixtures thereof, and in that the reaction is carried out in the presence of an aqueous base, and a water-immiscible organic solvent, said organic solvent mainly comprising at least one compound selected from C2-5-alkyl C2-5-carboxylates and mixtures of at least one C2-5-alkyl C2-5-carboxylate with at least one C5-8-alkane. Another aspect of the invention is directed to a process for the synthesis of said cyclic carbamate starting described above, wherein also a process for the preparation of the chiral propargylic alcohol is provided.

  本发明涉及一种以手性炔丙醇和/或适当的盐为起始物，通过选择光气、二光气、三光气及其混合物作为环化剂进行反应，以制备环状碳酸酯的方法，其中反应在水性碱和与水不混溶的有机溶剂的存在下进行，所述有机溶剂主要由至少一种C2-5-烷基C2-5-羧酸酯和至少一种C2-5-烷基C2-5-羧酸酯与至少一种C5-8-烷烃的混合物组成。发明的另一方面涉及上述描述的环状碳酸酯的合成过程，其中还提供了制备手性炔丙醇的方法。
• Über die Enantiomerentrennung durch Verteilung zwischen flüssigen Phasen. 3. Mitteilung. Selektivität der lipophilen Weinsäureester für chirale Ammonium-Salze verschiedener Konstitution und Konfiguration
  作者：Vladimir Prelog、Stjepan Mutak、Krunoslav Kovačević

  DOI：10.1002/hlca.19830660739

  日期：1983.11.2

  Separation of Enantiomers by Partition between Liquid Phases. 3. Communication. Selectivity of Lipophilic Tartaric Acid Esters for Chiral Ammonium Salts of Different Constitution and Configuration

  通过液相之间的分配分离对映异构体。3.沟通。亲脂性酒石酸酯对不同组成和构型的手性铵盐的选择性
• <i>B</i>-Allenyl- and <i>B-</i>(γ-Trimethylsilylpropargyl)- 10-phenyl-9-borabicyclo[3.3.2]decanes:  Asymmetric Synthesis of Propargyl and α-Allenyl 3°-Carbinols from Ketones
  作者：Eliud Hernandez、Carlos H. Burgos、Eyleen Alicea、John A. Soderquist

  DOI：10.1021/ol061596j

  日期：2006.8.1

  Simple and efficient Grignard procedures are reported for the syntheses of B-allenyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) and its B-(gamma-trimethylsilylpropargyl) counterpart (2) in both enantiomeric forms. Both add selectively to ketones, providing propargyl- and alpha-silylallenyl 3-degree-carbinols, respectively (i.e., 6 (61-93% ee) and 9 (64-98% ee)). The air-stable boron byproduct is efficiently

  据报道，简单有效的Grignard方法可合成两种对映体形式的B-烯基-10-（苯基）-9-环硼[3.3.2]癸烷（1）及其对应的B-（γ-三甲基甲硅烷基炔丙基）（2）。 。两者都选择性地添加到酮中，分别提供炔丙基和α-甲硅烷基烯丙基3-度羰基化合物（即6（61-93％ee）和9（64-98％ee））。空气稳定的硼副产物可有效回收并循环回1或2。9的臭氧分解和溴化分别提供非外消旋的α-羟基酸和γ-溴丙炔基甲醇。
• Process for the synthesis of chiral propargylic alcohols
  申请人：Lonza Ltd

  公开号：EP2447247A1

  公开（公告）日：2012-05-02

  A process for the synthesis of chiral propargylic alcohols.

  手性丙炔醇的合成过程。
• Process for the synthesis of cyclic carbamates
  申请人：Lonza Ltd

  公开号：EP2447255A1

  公开（公告）日：2012-05-02

  The invention is directed to a process for the preparation of a cyclic carbamate starting with a chiral propargylic alcohol and/or a suitable salt thereof, which is reacted with a cyclisation agent selected from phosgene, diphosgene, triphosgene and mixtures thereof, and in that the reaction is carried out in the presence of an aqueous base, and a water-immiscible organic solvent, said organic solvent mainly comprising at least one compound selected from C2-5-alkyl C2-5-carboxylates and mixtures of at least one C2-5-alkyl C2-5-carboxylate with at least one C5-8-alkane. Another aspect of the invention is directed to a process for the synthesis of said cyclic carbamate starting described above, wherein also a process for the preparation of the chiral propargylic alcohol is provided.

  该发明涉及一种以手性丙炔醇和/或其适当盐为起始物，与从光气、二光气、三光气和它们的混合物中选择的环化试剂反应，且在水性碱和水不相溶的有机溶剂存在下进行反应的制备环氧羰基化合物的方法，所述有机溶剂主要包括至少一种选择自C2-5-烷基C2-5-羧酸酯和至少一种C5-8-烷烃的混合物的化合物。该发明的另一个方面涉及一种合成上述环氧羰基化合物的方法，其中还提供了一种制备手性丙炔醇的方法。