benzylamino-phenyl-acetaldehyde dimethylacetal | 101582-03-0

• 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: benzylamino-phenyl-acetaldehyde dimethylacetal
• 英文别名: (+/-)-Benzyl-(2,2-dimethoxy-1-phenyl-aethyl)-amin；1-phenyl-2,2-dimethoxyethylamine；N-benzyl-2,2-dimethoxy-1-phenylethanamine
• CAS: 101582-03-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: RCJMDZRSPNOWOE-UHFFFAOYSA-N

物化性质

• 沸点：
  355.1±37.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  benzylamino-phenyl-acetaldehyde dimethylacetal 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 1.5h， 生成 (R)-2,2-dimethoxy-1-phenylethanamine
  参考文献：
  名称：

  某些α-氨基缩醛的拆分和绝对构型：对映纯N保护的α-氨基醛

  摘要：

  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。

  DOI：

  10.1007/s00726-011-1117-6
• 作为产物：
  描述：

  苄胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium iodide 作用下， 生成 benzylamino-phenyl-acetaldehyde dimethylacetal
  参考文献：
  名称：

  Boon, Journal of the Chemical Society, 1957, p. 2151

  摘要：

  DOI：

文献信息

• [EN] PROCESS FOR PREPARING ALPHA AMINOACETALS IN RECEMIC FORM<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION D'ALPHA-AMINOACÉTALS SOUS FORME RACÉMIQUE
  申请人：CLARIANT SPECIALTY FINE CHEM

  公开号：WO2010031544A1

  公开（公告）日：2010-03-25

  The invention relates to a process for preparing an α-aminoacetal, or addition salts thereof, of formula (I) in recemic form comprising the steps consisting in: reacting a glyoxal monoacetal of formula (II) with an arylalkylamine of formula (III) in such a way as to obtain an imine of formula (IV); adding a Grignard reagent of formula R3-Mg-HaI to said imine of formula (IV) so as to obtain an amine of formula (V), and - deprotecting the amine of formula (V) in such a way as to obtain the compound of formula (I) in racemic form, and, where appropriate, adding an inorganic or organic acid in order to obtain an addition salt of the α-aminoacetal of formula (I).

  该发明涉及一种制备α-氨基缩醛或其盐的方法，以消旋形式表示，包括以下步骤：将式（II）的甘醛单缩醛与式（III）的芳基烷胺反应，从而获得式（IV）的亚胺；将式（IV）的亚胺与式R3-Mg-HaI的格氏试剂反应，从而获得式（V）的胺；去保护式（V）的胺，以获得消旋形式的式（I）化合物，并在必要时添加无机或有机酸，以获得式（I）的α-氨基缩醛的盐。
• Synthesis and Reactivity of Bicycles Derived from Tartaric Acid and α-Amino Acids:  A Novel Class of Conformationally Constrained Dipeptide Isosteres Based upon Enantiopure 3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic Acid
  作者：Antonio Guarna、Antonio Guidi、Fabrizio Machetti、Gloria Menchi、Ernesto G. Occhiato、Dina Scarpi、Sauro Sisi、Andrea Trabocchi

  DOI：10.1021/jo9904967

  日期：1999.10.1

  3-Aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acids (named BTAa) derived from (R,R), (S,S)-, or meso-tartaric acid and natural (L), unnatural (D), or unusual alpha-amino acids are described as conformationally constrained dipeptide isosteres. The general strategy developed for their preparation has required the transformation of the amino acids into the corresponding N-benzylamino alcohols, followed by the PyBroP-promoted condensation with the monomethyl ester of the suitable 2,3-di-O-isopropylidenetartaric acid. Oxidation of the hydroxy group to aldheyde and subsequent acid-catalyzed trans-acetalization with the two hydroxy groups of the tartaric acid moiety provided 3-aza-2-oxo-6,8-dioxabicyclo [3.2.1] octane-7-carboxylic acid methyl esters [named BTAa(O)] in good yield and, in most cases, as single enantiopure diastereoisomers. This strategy has been applied to the preparation of BTAa(O) starting from (R,R)-, (S,S)-, or meso-tartaric acid and glycine, L- and D-phenylalanine, L- and D-alanine, and (+/-)-phenylglycine. In the cases of glycine, L- and D-phenylalanine, and L- and D-alanine, the selective reduction by BH3. DMS of the amide group succeeding to the cyclization step, or the reduction of both amide and ester functions followed by reoxidation of the hydroxy to carboxylic group, provided in good yield the 3-aza-3-benzyl-6,8-dioxabicyclo[3.2.1]-octane-7-carboxylic acids (or their methyl ester) BTAa, having the side chain of the amino acid precursors at position 4. The stability and rigidity of the bicyclic skeleton, the complete control of all the stereocenters, the possibility of introducing the side chains of L- or D-amino acids, and the demonstrated compatibility with the conditions required for solid-phase peptide synthesis make the BTAa compounds potential dipeptide isosteres useful for the synthesis of modified peptides.
• 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。
• Boon, Journal of the Chemical Society, 1957, p. 2151
  作者：Boon

  DOI：——

  日期：——