1-(R)-(tert-butoxycarbonyl)-2-phenylethyl chloroformate | 1257267-18-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(R)-(tert-butoxycarbonyl)-2-phenylethyl chloroformate
• CAS: 1257267-18-7
• 化学式: C₁₄H₁₇ClO₄
• 分子量: 284.74
• InChiKey: PKIQVZSXGRWQFP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(苄羰氧基)羟基胺 、 1-(R)-(tert-butoxycarbonyl)-2-phenylethyl chloroformate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以33%的产率得到N-(benzyloxycarbonyl)-O-[1-(R)-(tert-butoxycarbonyl)-2-phenylethoxycarbonyl]hydroxylamine
  参考文献：
  名称：

  Serendipitous Discovery of α-Hydroxyalkyl Esters as β-Lactamase Substrates

  摘要：

  O-(1-Carboxy-1-alkyloxycarbonyl) hydroxamates were found to spontaneously decarboxylate in aqueous neutral buffer to form O-(2-hydroxyalkylcarbonyl) hydroxamates, While the former molecules do not react rapidly with serine beta-lactamases, the latter are quite good substrates of representative class A and C, but not D, enzymes, and particularly of a class C enzyme. The enzymes catalyze hydrolysis of these compounds to a mixture of the alpha-hydroxy acid and hydroxamate. Analogous compounds containing aryloxy leaving groups rather that hydroxamates are also substrates. Structure-activity experiments showed that the alpha-hydroxyl group was required for any substantial substrate activity. Although both D- and L-alpha-hydroxy acid derivatives were substrates, the former were preferred. The response of the class C activity to pH and to alternative nucleophiles (methanol and D-phenylalanine) suggested that the same active site functional groups participated in catalysis as for classical substrates. Molecular modeling was employed to explore how the alpha-hydroxy group might interact with the class C beta-lactamase active site. Incorporation of the alpha-hydroxyalkyl moiety into novel inhibitors will be of considerable interest.

  DOI：

  10.1021/bi101071r
• 作为产物：
  描述：

  D-3-苯乳酸 在 4-二甲氨基吡啶 、 乙酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 28.33h， 生成 1-(R)-(tert-butoxycarbonyl)-2-phenylethyl chloroformate
  参考文献：
  名称：

  Serendipitous Discovery of α-Hydroxyalkyl Esters as β-Lactamase Substrates

  摘要：

  O-(1-Carboxy-1-alkyloxycarbonyl) hydroxamates were found to spontaneously decarboxylate in aqueous neutral buffer to form O-(2-hydroxyalkylcarbonyl) hydroxamates, While the former molecules do not react rapidly with serine beta-lactamases, the latter are quite good substrates of representative class A and C, but not D, enzymes, and particularly of a class C enzyme. The enzymes catalyze hydrolysis of these compounds to a mixture of the alpha-hydroxy acid and hydroxamate. Analogous compounds containing aryloxy leaving groups rather that hydroxamates are also substrates. Structure-activity experiments showed that the alpha-hydroxyl group was required for any substantial substrate activity. Although both D- and L-alpha-hydroxy acid derivatives were substrates, the former were preferred. The response of the class C activity to pH and to alternative nucleophiles (methanol and D-phenylalanine) suggested that the same active site functional groups participated in catalysis as for classical substrates. Molecular modeling was employed to explore how the alpha-hydroxy group might interact with the class C beta-lactamase active site. Incorporation of the alpha-hydroxyalkyl moiety into novel inhibitors will be of considerable interest.

  DOI：

  10.1021/bi101071r