(R)-1-benzyl-2,2-dimethoxyethylamine | 1084820-36-9

• 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: (R)-1-benzyl-2,2-dimethoxyethylamine
• 英文别名: D-phenylalanine dimethyl acetal；(2R)-1,1-dimethoxy-3-phenylpropan-2-amine
• CAS: 1084820-36-9
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: IFUOZMQFLICJQQ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-benzyl-2,2-dimethoxyethylamine 在 sodium tungstate 双氧水 作用下， 以 水 为溶剂， 以78%的产率得到1,1-dimethoxy-3-phenylpropan-2-one oxime
  参考文献：
  名称：

  WO2008/142088

  摘要：

  公开号：
• 作为产物：
  描述：

  (R)-1-benzyl-2,2-dimethoxyethylammonium N-acetyl-(L)-phenylalaninate 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (R)-1-benzyl-2,2-dimethoxyethylamine
  参考文献：
  名称：

  [EN] PROCESS OF PREPARATION OF OPTICALLY ACTIVE ALPHA AMINOACETALS
  [FR] PRÉPARATION D'ALPHA AMINOCÉTALS OPTIQUEMENT ACTIFS

  摘要：

  该发明涉及一种制备光学活性α-氨基缩醛的方法，通过分离外消旋混合物或对映异构体混合物，通过形成二对映异构盐，并且还涉及以二对映异构盐形式存在的新型中间体。

  公开号：

  WO2009106386A1

文献信息

• Resolution and absolute configuration of some α-aminoacetals: en route to enantiopure N-protected α-aminoaldehydes
  作者：Muriel Albalat-Serradeil、Géraldine Primazot、Didier Wilhelm、Jean-Claude Vallejos、Nicolas Vanthuyne、Christian Roussel

  DOI：10.1007/s00726-011-1117-6

  日期：2012.8

  The first successful resolution of rac-α-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of α-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected α-aminoaldehyde

  据报道，通过与光学纯的N-保护的氨基酸形成非对映异构体盐，成功地分离了rac - α-氨基缩醛。α-氨基缩醛对映异构体的绝对构型分配是通过涉及N-保护的完全非消旋化学相关方法和新的有效水解步骤，然后还原所得的N-保护的α-氨基醛中间体进行的。举例说明了光学富集的α-氨基缩醛的消旋方法，以使两种对映异构体均价。
• Catalytic Diastereoselective Petasis Reactions
  作者：Giovanni Muncipinto、Philip N. Moquist、Stuart L. Schreiber、Scott E. Schaus

  DOI：10.1002/anie.201103271

  日期：2011.8.22

  Multicomponent Petasis reactions: The first diastereoselective Petasis reaction catalyzed by chiral biphenols that enables the synthesis of syn and anti β‐amino alcohols in pure form has been developed. The reaction exploits a multicomponent approach that involves boronates, α‐hydroxy aldehydes, and amines (see scheme).

  多组分 Petasis 反应：第一个由手性联苯酚催化的非对映选择性 Petasis 反应已经开发出来，该反应能够合成纯形式的顺式和反式 β-氨基醇。该反应采用多组分方法，涉及硼酸盐、α-羟基醛和胺（参见方案）。
• Process of racemisation of optically active alpha aminoacetals
  申请人：Clariant Specialty Fine Chemicals (France)

  公开号：US08350092B2

  公开（公告）日：2013-01-08

  The invention relates to a process for preparing α-aminoacetals substantially in racemic form, comprising a step of oxidizing optically enriched α-aminoacetals to the corresponding oximes, in the presence of a catalyst, and a step of reducing the oximes thus obtained.

  本发明涉及一种制备基本上为外消旋形式的α-氨基缩醛的方法，包括在催化剂的存在下，将光学纯度较高的α-氨基缩醛氧化成相应的肟，以及还原所得到的肟的步骤。
• On the inhibition of HIV-1 protease by hydrazino-ureas displaying the N→CO interaction
  作者：Michael Waibel、Delphine Pitrat、Jens Hasserodt

  DOI：10.1016/j.bmc.2009.03.059

  日期：2009.5

  To create novel HIV-1 protease (HIV PR) inhibitors, we have extended our investigations of the N -> C=O interaction as a moiety that reproduces electrostatic properties of the transition state of peptidolysis. Consequently, we prepared a series of compounds with an unusual hydrazino-urea core. In polar protic media, these adopt solely a cyclic constitution displaying the interaction on one side of the molecule while offering a urea moiety on the opposite side meant to hydrogen-bond with the enzyme flaps. Each inhibitor candidate was obtained via a key series of three synthetic steps employing carbonyl-di-imidazole (CDI). It was thus possible to efficiently fuse two independent building blocks, a hydrazine and a protected aminoaldehyde in a convergent manner. NMR and UV analysis proved that all compounds, when dissolved in polar protic media, existed exclusively in the cyclic constitution exhibiting the N -> C=O interaction. In total, five inhibitor candidates were tested with HIV PR for their potency. The one carrying the least bulk in peripheral substituents showed the highest activity. Its very low molecular weight ( 365 g/mol) holds great promise for future improvements in affinity without violating Lipinski's rule of remaining within the limit of 500 g/mol. (C) 2009 Elsevier Ltd. All rights reserved.
• PROCESS OF RACEMISATION OF OPTICALLY ACTIVE ALPHA AMINOACETALS
  申请人：Clariant Specialty Fine Chemicals (France)

  公开号：EP2162426B1

  公开（公告）日：2013-01-02