2-acetoxymethyl-2-methyl-3-phenylpropanol | 594837-80-6

• 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: 2-acetoxymethyl-2-methyl-3-phenylpropanol
• 英文别名: (2-Benzyl-3-hydroxy-2-methylpropyl) acetate；(2-benzyl-3-hydroxy-2-methylpropyl) acetate
• CAS: 594837-80-6
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: DLJZNPKKBWSSJA-UHFFFAOYSA-N

物化性质

• 沸点：
  323.0±30.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-acetoxymethyl-2-methyl-3-phenylpropanol 在 sodium hydroxide 、 jones reagent 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 (2S,1'S)-2-hydroxymethyl-2-methyl-3-phenyl-N-(1'-phenylethyl)propionamide
  参考文献：
  名称：

  Synthesis and evaluation of α,α-disubstituted-3-mercaptopropanoic acids as inhibitors for carboxypeptidase A and implications with respect to enzyme inhibitor design

  摘要：

  2-Ethyl-2-meth% 1-3-mercaptopropanoic acid (6) and 2-benzyl-2-methyl-3-mercaptopropanoic acid (7) were synthesized and evaluated as inhibitors for carboxypeptidase A (CPA), a prototypical zinc protease with the expectation that the binding affinities of these inhibitors would be augmented over those of 2-ethyl-3-methylsuccinic acid (2) and 2-benzyl-3-methylsuccinic acid (3), respectively, in light of the fact that the sulfhydryl group is a better zinc coordinating moiety than the carboxylate group. Contrary to the expectation. however. the inhibitory potency of 6 was not improved and that of 7 was rather attenuated by the replacement. A probable explanation for the unexpected results is offered. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.017
• 作为产物：
  描述：

  2-benzyl-2-methylmalonic acid diethyl ester 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-acetoxymethyl-2-methyl-3-phenylpropanol
  参考文献：
  名称：

  Synthesis and evaluation of α,α-disubstituted-3-mercaptopropanoic acids as inhibitors for carboxypeptidase A and implications with respect to enzyme inhibitor design

  摘要：

  2-Ethyl-2-meth% 1-3-mercaptopropanoic acid (6) and 2-benzyl-2-methyl-3-mercaptopropanoic acid (7) were synthesized and evaluated as inhibitors for carboxypeptidase A (CPA), a prototypical zinc protease with the expectation that the binding affinities of these inhibitors would be augmented over those of 2-ethyl-3-methylsuccinic acid (2) and 2-benzyl-3-methylsuccinic acid (3), respectively, in light of the fact that the sulfhydryl group is a better zinc coordinating moiety than the carboxylate group. Contrary to the expectation. however. the inhibitory potency of 6 was not improved and that of 7 was rather attenuated by the replacement. A probable explanation for the unexpected results is offered. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.017

文献信息

• Synthesis and evaluation of α,α-disubstituted-3-mercaptopropanoic acids as inhibitors for carboxypeptidase A and implications with respect to enzyme inhibitor design
  作者：Hyun Soo Lee、Dong H Kim

  DOI：10.1016/j.bmc.2003.08.017

  日期：2003.11

  2-Ethyl-2-meth% 1-3-mercaptopropanoic acid (6) and 2-benzyl-2-methyl-3-mercaptopropanoic acid (7) were synthesized and evaluated as inhibitors for carboxypeptidase A (CPA), a prototypical zinc protease with the expectation that the binding affinities of these inhibitors would be augmented over those of 2-ethyl-3-methylsuccinic acid (2) and 2-benzyl-3-methylsuccinic acid (3), respectively, in light of the fact that the sulfhydryl group is a better zinc coordinating moiety than the carboxylate group. Contrary to the expectation. however. the inhibitory potency of 6 was not improved and that of 7 was rather attenuated by the replacement. A probable explanation for the unexpected results is offered. (C) 2003 Elsevier Ltd. All rights reserved.