N-phenylacetyl-D-Ala methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-phenylacetyl-D-Ala methyl ester
• 英文别名: methyl (2R)-2-[(2-phenylacetyl)amino]propanoate
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: DLCNTEDUKYKOIF-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenylacetyl-D-Ala methyl ester 在 sodium phosphate buffer 、 penicillin-G amidase from E_. coli 作用下， 反应 24.0h， 生成 D-丙氨酸甲酯
  参考文献：
  名称：

  Quantitative enzymatic protection of d-amino acid methyl esters by exploiting ‘relaxed’ enantioselectivity of penicillin-G amidase in organic solvent

  摘要：

  The lower enantio selectivity displayed by penicillin-G amidase (PGA) from E. coli in organic solvent has been exploited for developing a facile, fast and quantitative method for protection of esters of various D-amino acids via N-acylation. The feasibility of the deprotection of the acylated products was also demonstrated by employing PGA from two different sources in aqueous media. Experimental results are in agreement with previous calculations based on in silico models of the enzyme active site. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.153
• 作为产物：
  描述：

  N,N-二甲基苄胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 、 三苯基膦 作用下， 以 乙醚 、 二甲基亚砜 、 甲苯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 12.5h， 生成 N-phenylacetyl-D-Ala methyl ester
  参考文献：
  名称：

  钯通过C–N键活化将苄基铵盐羰基化为酰胺和酯†

  摘要：

  首次报道了一种有效的钯催化的季铵盐与CO的有效的羰基催化羰基化反应，可通过苄基的C–N键裂解产生芳基乙酰胺和芳基酸酯。该方案的特点是在CO的大气压下具有温和的反应条件，无需其他氧化剂即可进行的氧化还原中性工艺，以及适用于各种胺，醇和酚的广泛底物范围。

  DOI：

  10.1039/c8ob00488a

文献信息

• Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters <i>via</i> C–N bond activation
  作者：Weijie Yu、Shuwu Yang、Fei Xiong、Tianxiang Fan、Yan Feng、Yuanyuan Huang、Junkai Fu、Tao Wang

  DOI：10.1039/c8ob00488a

  日期：——

  An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C–N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various

  首次报道了一种有效的钯催化的季铵盐与CO的有效的羰基催化羰基化反应，可通过苄基的C–N键裂解产生芳基乙酰胺和芳基酸酯。该方案的特点是在CO的大气压下具有温和的反应条件，无需其他氧化剂即可进行的氧化还原中性工艺，以及适用于各种胺，醇和酚的广泛底物范围。
• Quantitative enzymatic protection of d-amino acid methyl esters by exploiting ‘relaxed’ enantioselectivity of penicillin-G amidase in organic solvent
  作者：Chiara Carboni、Peter J.L.M. Quaedflieg、Quirinus B. Broxterman、Paolo Linda、Lucia Gardossi

  DOI：10.1016/j.tetlet.2004.10.153

  日期：2004.12

  The lower enantio selectivity displayed by penicillin-G amidase (PGA) from E. coli in organic solvent has been exploited for developing a facile, fast and quantitative method for protection of esters of various D-amino acids via N-acylation. The feasibility of the deprotection of the acylated products was also demonstrated by employing PGA from two different sources in aqueous media. Experimental results are in agreement with previous calculations based on in silico models of the enzyme active site. (C) 2004 Elsevier Ltd. All rights reserved.