N-[(R)-2-hydroxy-1-phenylethyl]-N-methyl-2-phenylacetamide | 160247-37-0

• 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: N-[(R)-2-hydroxy-1-phenylethyl]-N-methyl-2-phenylacetamide
• 英文别名: N-[(1R)-2-hydroxy-1-phenylethyl]-N-methyl-2-phenylacetamide
• CAS: 160247-37-0
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: PYOHWLXPNYIFQB-INIZCTEOSA-N

物化性质

• 熔点：
  73-74 °C
• 沸点：
  458.8±45.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(R)-2-hydroxy-1-phenylethyl]-N-methyl-2-phenylacetamide 在 palladium dihydroxide 硼烷四氢呋喃络合物 、 仲丁基锂 、 lithium chloride 、 环己烯 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 (R)-4-Methylamino-3-phenyl-butyric acid
  参考文献：
  名称：

  Enantioselective Synthesis of β-Substituted Primary and Secondary Amines by Alkylation of (R)-Phenylglycinol Amide Enolates

  摘要：

  描述了一种通用且便利的光学活性β-取代的次级或主要胺4和8的合成方法。该方法基于对从R-(-)-苯基甘氨醇衍生的酰胺1和5的非对映选择性烷基化，随后进行还原和去除手性附属物。这一程序还用于制备1,4-氨基醇12和γ-氨基酯14。

  DOI：

  10.1055/s-1997-1303
• 作为产物：
  描述：

  (R)-2-(甲基氨基)-2-苯基乙醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到N-[(R)-2-hydroxy-1-phenylethyl]-N-methyl-2-phenylacetamide
  参考文献：
  名称：

  Origins of diastereoselectivity in the alkylation of N-substituted lactams and amides derived from optically active aminoalcohols

  摘要：

  The origins of diastereoselectivity in the alkylation of lactams la and Ib and amides 6a and 6b are discussed. A rigid intermediate in which the pyramidalized amide nitrogen chelated the alkoxide lithium cation is invoked. Further experiments conducted with different substrates' are in agreement with the proposed model, Furthermore this model can explain the differences observed previously between ephedrine and pseudoephedrine amide alkylation. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00374-6

文献信息

• Synthesis of carboxylic amides by ring-opening of oxazolidinones with Grignard reagents
  作者：David Bensa、Iain Coldham、Pia Feinäugle、Ravindra B. Pathak、Roger J. Butlin

  DOI：10.1039/b800849c

  日期：——

  including allyl, benzyl, alkyl and phenyl magnesium halides. The organomagnesium species attacks the carbonyl group and promotes ring-opening of the oxazolidinone. The product tertiary amides are useful substrates for stereoselective transformations and were applied to a highly selective enolate alkylation and to a ring-closing metathesis reaction to a six-membered lactam and hence a formal synthesis of the

  用格氏试剂处理N-烷基-恶唑烷-2-酮可得到叔羧酸酰胺产物。可以使用各种取代的恶唑烷酮，如在4-位上具有苯基，苄基或异丙基，在3-位（氮原子）上具有甲基，苄基或对甲氧基苄基所示。成功选择了格氏试剂，包括烯丙基，苄基，烷基和苯基卤化镁。有机镁物质攻击羰基并促进恶唑烷酮的开环。产物叔酰胺是用于立体选择性转化的有用底物，并用于高度选择性的烯醇烷基化和六元内酰胺的闭环易位反应，从而正式合成生物碱（-）-丝氨酸和（+） -stenusine。
• Asymmetric synthesis. XXXIII. Diastereoselective alkylation of N,N-substituted amides
  作者：Laurent Micouin、Vincent Schanen、Claude Riche、Angèle Chiaroni、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1016/0040-4039(94)85366-5

  日期：1994.9

  A series of α-substituted amides 3 and 7–9 has been synthesized in enantiomerically pure form by diastereoselective alkylation of N-alkyl phenylglycinol amides 2 and 4–6 respectively. A rigid amide enolate has been postulated to explain the observed diastereoselectivity.

  通过对映体纯净的形式分别通过N-烷基苯基甘氨醇酰胺2和4-6的非对映选择性烷基化合成了一系列α-取代的酰胺3和7-9。已假定使用刚性酰胺烯酸酯来解释观察到的非对映选择性。
• Origins of diastereoselectivity in the alkylation of N-substituted lactams and amides derived from optically active aminoalcohols
  作者：Laurent Micouin、Valérie Jullian、Jean-Charles Quirion、Henri-Philippe Husson

  DOI：10.1016/0957-4166(96)00374-6

  日期：1996.10

  The origins of diastereoselectivity in the alkylation of lactams la and Ib and amides 6a and 6b are discussed. A rigid intermediate in which the pyramidalized amide nitrogen chelated the alkoxide lithium cation is invoked. Further experiments conducted with different substrates' are in agreement with the proposed model, Furthermore this model can explain the differences observed previously between ephedrine and pseudoephedrine amide alkylation. Copyright (C) 1996 Elsevier Science Ltd
• Enantioselective Synthesis of β-Substituted Primary and Secondary Amines by Alkylation of (R)-Phenylglycinol Amide Enolates
  作者：Valérie Jullian

  DOI：10.1055/s-1997-1303

  日期：1997.9

  General and convenient syntheses of optically active β-substituted secondary or primary amines 4 and 8 are described. The method is based on diastereoselective alkylation of amides 1 and 5 derived from R-(-)-phenylglycinol followed by reduction and removal of the chiral appendage. This procedure has also been applied to the preparation of 1,4-amino alcohols 12 and γ-amino esters 14.

  描述了一种通用且便利的光学活性β-取代的次级或主要胺4和8的合成方法。该方法基于对从R-(-)-苯基甘氨醇衍生的酰胺1和5的非对映选择性烷基化，随后进行还原和去除手性附属物。这一程序还用于制备1,4-氨基醇12和γ-氨基酯14。