(S)-(-)-(1-phenylethylamino)acetaldehyde dimethyl acetal | 162872-57-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(-)-(1-phenylethylamino)acetaldehyde dimethyl acetal
• 英文别名: 2,2-dimethoxy-N-[(1S)-1-phenylethyl]ethanamine
• CAS: 162872-57-3
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: HBIXOIOMBMDWQG-JTQLQIEISA-N

物化性质

• 沸点：
  265.4±25.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-(1-phenylethylamino)acetaldehyde dimethyl acetal 在 盐酸 、 potassium thioacyanate 、 镍 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 8.08h， 生成 1-[(1S)-1-苯基乙基]咪唑
  参考文献：
  名称：

  Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

  DOI：

  10.1021/jo00112a023
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 18.0h， 生成 (S)-(-)-(1-phenylethylamino)acetaldehyde dimethyl acetal
  参考文献：
  名称：

  (+)-6,7-二甲氧基-1,2,3,4-四氢异喹啉-1-羧酸的合成，非对映选择性方法

  摘要：

  (+)-6,7-二甲氧基-1,2,3,4-四氢异喹啉-1-羧酸(90%ee)的非对映选择性合成是通过两种合成方法的组合完成的，即Petasis合成氨基酸和四氢异喹啉衍生物的 Pomeranz-Fritsch-Bobbitt 合成。合成的立体化学结果由手性氨基乙醛缩醛控制，手性氨基乙醛缩醛用作 Petasis 步骤的胺组分，以在一个简单的操作中产生用于四氢异喹啉环形成的 Pomeranz-Fritsch-Bobbitt 底物。

  DOI：

  10.1002/ejoc.201403218

文献信息

• Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles
  作者：Federico Corelli、Vincenzo Summa、Alessandra Brogi、Edith Monteagudo、Maurizio Botta

  DOI：10.1021/jo00112a023

  日期：1995.4

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.
• Synthesis of (+)-6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acid, a Diastereoselective Approach
  作者：Ilona Bułyszko、Maria Chrzanowska、Agnieszka Grajewska、Maria D. Rozwadowska

  DOI：10.1002/ejoc.201403218

  日期：2015.1

  The diastereoselective synthesis of (+)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (90 % ee) was accomplished by employing a combination of two synthetic methods, that is, the Petasis synthesis of amino acids and the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline derivatives. The stereochemical outcome of the synthesis was controlled by chiral aminoacetaldehyde acetals

  (+)-6,7-二甲氧基-1,2,3,4-四氢异喹啉-1-羧酸(90%ee)的非对映选择性合成是通过两种合成方法的组合完成的，即Petasis合成氨基酸和四氢异喹啉衍生物的 Pomeranz-Fritsch-Bobbitt 合成。合成的立体化学结果由手性氨基乙醛缩醛控制，手性氨基乙醛缩醛用作 Petasis 步骤的胺组分，以在一个简单的操作中产生用于四氢异喹啉环形成的 Pomeranz-Fritsch-Bobbitt 底物。