ethyl 3-hydroxy-3-phenylpropionate-d2 | 166280-30-4

• 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: ethyl 3-hydroxy-3-phenylpropionate-d2
• CAS: 166280-30-4
• 化学式: C₁₁H₁₄O₃
• 分子量: 196.214
• InChiKey: DVIBDQWVFHDBOP-MGVXTIMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-3-phenylpropionate-d2 在 palladium on activated charcoal 氘代甲醇-d 、 氘代乙腈 、 氢气 、 三甲基铝 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 4-phenyl N-(tosyloxy)-2-azetidinone-4-d2
  参考文献：
  名称：

  Potent mechanism-based inhibition of the TEM-1 .beta.-lactamase by novel N-sulfonyloxy .beta.-lactams

  摘要：

  A novel class of N-sulfonyloxy beta-lactam molecules are described as potent mechanism-based inactivators for the bacterial TEM-1 beta-lactamase, a prototypic class A enzyme. These molecules inactivate the enzyme with k(inact)/K-i values in the range of 1-7 x 10(4) M(-1) s(-1) and partition ratios (i.e., k(cat)/k(inact)) of 2-7. The mechanism of action of these inactivators was investigated. These molecules acylate the active-site serine of the TEM-1 beta-lactamase, a process that results in the release of the sulfonate attached to the lactam nitrogen, giving rise to a proposed beta-amino cinnamoyl derivative as the inhibitory species. This species undergoes gradual hydrolysis with concomitant recovery of activity, the rate constants for which were evaluated.

  DOI：

  10.1021/ja00127a005
• 作为产物：
  描述：

  ethyl benzoylacetate-d2 在 sodium tetrahydroborate 、 氘代甲醇-d 作用下， 反应 0.5h， 以71%的产率得到ethyl 3-hydroxy-3-phenylpropionate-d2
  参考文献：
  名称：

  Potent mechanism-based inhibition of the TEM-1 .beta.-lactamase by novel N-sulfonyloxy .beta.-lactams

  摘要：

  A novel class of N-sulfonyloxy beta-lactam molecules are described as potent mechanism-based inactivators for the bacterial TEM-1 beta-lactamase, a prototypic class A enzyme. These molecules inactivate the enzyme with k(inact)/K-i values in the range of 1-7 x 10(4) M(-1) s(-1) and partition ratios (i.e., k(cat)/k(inact)) of 2-7. The mechanism of action of these inactivators was investigated. These molecules acylate the active-site serine of the TEM-1 beta-lactamase, a process that results in the release of the sulfonate attached to the lactam nitrogen, giving rise to a proposed beta-amino cinnamoyl derivative as the inhibitory species. This species undergoes gradual hydrolysis with concomitant recovery of activity, the rate constants for which were evaluated.

  DOI：

  10.1021/ja00127a005