(R)-N-phenylacetyl-2-amino-4-phenylbutane | 331003-50-0

• 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: (R)-N-phenylacetyl-2-amino-4-phenylbutane
• 英文别名: N-phenylacetyl-(R)-2-amino-4-phenylbutane；2-phenyl-N-[(2R)-4-phenylbutan-2-yl]acetamide
• CAS: 331003-50-0
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: WOCGROGRPWVPJP-OAHLLOKOSA-N

物化性质

• 沸点：
  469.4±34.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基-3-苯基丙胺 、 2-苯乙酰胺 在 penicillin acylase from Alcaligenes faecalis 作用下， 以 水 为溶剂， 反应 0.08h， 以40%的产率得到(R)-N-phenylacetyl-2-amino-4-phenylbutane
  参考文献：
  名称：

  水性介质中胺的高效和对映选择性酶促酰化

  摘要：

  已经开发了一种基于相对未知的粪便产青霉素的青霉素酰基转移酶的独特催化特性，稳定性和对映选择性的新策略，用于在水性介质中对胺进行有效和对映选择性的酰化。与有机溶剂中的脂肪酶催化的酰化反应相反，青霉素酰化酶催化的水溶液中胺的酰化反应是一种快速的化学选择性过程，可导致产物随后被相同的酶脱酰，进行二次对映体控制并导致有效的拆分。 。

  DOI：

  10.1016/s0957-4166(01)00263-4

文献信息

• Method for the preparation of enantiomerically enriched amines
  申请人：——

  公开号：US20040014181A1

  公开（公告）日：2004-01-22

  Method for the preparation of an enantiomerically enriched acylated amine wherein a phenylacetic acid derivative is brought into contact with a mixture of enantiomers of an amine H 2 NCR 1 R 2 R 3 , in which R 1 , R 2 , R 3 are not equal to each other and each independently stand for H, CN, a whether or not substituted (cyclo)alkyl, ary-, alkylaryl or arylalkyl group, whether or not cyclic heteroalkyl or heteroaryl group with one or more N, O or S atoms or in which R 1 and R 2 (and R 3 ) together with the C-atom to which they have been bound form a (bi)cyclic group that optionally contains one or more N, O of S atoms, in the presence of a Pen-G acylase derived from Alcaligenes faecalis. And method for the preparation of enantiomerically enriched amine of formula H 2 NCR 1 R 2 R 3 , in which R 1 , R 2 , R 3 are as defined above, wherein an acylated amine is brought into contact with a Pen-G acylase originating from Alcaligenes faecalis . Preferably enantiomerically enriched phenylglycine amide or an ester of p-hydroxyphenylglycine is applied as phenylacetic acid derivative.

  制备对映体富集的酰化胺的方法，其中将苯乙酸衍生物与胺的对映体混合物 H 2 NCR 1 R 2 R 3 其中 R 1 , R 2 , R 3 互不相等，且各自独立地代表 H、CN、一个或多个 N、O 或 S 原子取代的 （环）烷基、芳基、烷芳基或芳烷基、带有一个或多个 N、O 或 S 原子的环状杂烷基或杂芳基，或其中 R 1 和 R 2 (和 R 3 与它们结合的 C 原子一起形成一个（双）环状基团，该基团可选择含有一个或多个 N、O 或 S 原子。 粪阿卡菌。 以及制备对映体富集的式 H 2 NCR 1 R 2 R 3 其中 R 1 , R 2 , R 3 如上定义，其中，酰化胺与源自以下物质的 Pen-G 型酰化酶接触 粪酵母菌 .最好使用对映体富集的苯甘氨酸酰胺或对羟基苯甘氨酸酯作为苯乙酸衍生物。
• Penicillin acylase-catalyzed resolution of amines in aqueous organic solvents
  作者：L.M. van Langen、N.H.P. Oosthoek、D.T. Guranda、F. van Rantwijk、V.K. Švedas、R.A. Sheldon

  DOI：10.1016/s0957-4166(00)00442-0

  日期：2000.11

  Penicillin acylase from Alcaligenes faecalis catalyzes the enantioselective acylation of amines with phenylacetamide in a kinetically controlled reaction in water at pH II. Addition of cosolvent to the reaction mixture significantly improved the enantioselectivity in most cases. Penicillin acylase from E. coli also catalyzed the phenylacetylation of amines, but an order of magnitude less efficiently than with the enzyme of A. faecalis. Amine resolution via kinetically controlled acylation competes effectively with hydrolysis of N-acylated compounds and constitutes a synthetically useful alternative to existing lipase-based methods. (C) 2000 Elsevier Science Ltd. All rights reserved.
• METHOD FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED AMINES
  申请人：DSM N.V.

  公开号：EP1315827A1

  公开（公告）日：2003-06-04
• US6897058B2
  申请人：——

  公开号：US6897058B2

  公开（公告）日：2005-05-24
• [EN] METHOD FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED AMINES<br/>[FR] PROCEDE PERMETTANT LA PREPARATION D'AMINES ENRICHIES EN ENANTIOMERES
  申请人：DSM NV

  公开号：WO2002020820A1

  公开（公告）日：2002-03-14

  Method for the preparation of an enantiomerically enriched acylated amine wherein a phenylacetic acid derivative is brought into contact with a mixture of enantiomers of an amine H2NCR1R2R3, in which R1, R2, R3 are not equal to each other and each independently stand for H, CN, a whether or not substituted (cyclo)alkyl, ary-, alkylaryl or arylalkyl group, whether or not cyclic heteroalkyl or heteroaryl group with one or more N, O or S atoms or in which R1 and R2 (and R3) together with the C-atom to which they have been bound form a (bi)cyclic group that optionally contains one or more N, O of S atoms, in the presence of a Pen-G acylase derived from Alcaligenes faecalis. And method for the preparation of enantiomerically enriched amine of formula H2NCR1R2R3, in which R1, R2, R3 are as defined above, wherein an acylated amine is brought into contact with a Pen-G acylase originating from Alcaligenes faecalis. Preferably enantiomerically enriched phenylglycine amide or an ester of p-hydroxyphenylglycine is applied as phenylacetic acid derivative.