tert-butyl 1,4-dioxo-1H-benzo[d][1,2]oxazine-3(4H)-carboxylate | 31583-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: tert-butyl 1,4-dioxo-1H-benzo[d][1,2]oxazine-3(4H)-carboxylate
• 英文别名: tert-butyl 1,4-dioxo-1,4-dihydro-3H-benzo[d][1,2]oxazine-3-carboxylate；3-t-Butyloxycarbonyl-1,4-dioxo-3,4-dihydro-benzo-1,2-oxazin；1,4-dioxo-1,4-dihydro-benzo[d][1,2]oxazine-3-carboxylic acid tert-butyl ester；Tert-butyl 1,4-dioxo-2,3-benzoxazine-3-carboxylate
• CAS: 31583-38-7
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: BXVKMDGLLVDDHI-UHFFFAOYSA-N

物化性质

• 沸点：
  366.8±25.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 1,4-dioxo-1H-benzo[d][1,2]oxazine-3(4H)-carboxylate 在 盐酸 作用下， 以 乙醚 、 硝基甲烷 为溶剂， 生成 benzo-3-methyl-2,3-oxazine-1,4-dione
  参考文献：
  名称：

  Synthese von 1,4-Dioxo-3,4-dihydro-benzo[d]-1,2-oxazin (O,N-Phthaloyl-hydroxylamin)¹

  摘要：

  DOI：

  10.1055/s-1971-21685
• 作为产物：
  描述：

  N-羟基氨基甲酸叔丁酯 、 邻苯二甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以56%的产率得到tert-butyl 1,4-dioxo-1H-benzo[d][1,2]oxazine-3(4H)-carboxylate
  参考文献：
  名称：

  炔烃邻苯二甲酸酯的立体选择性合成

  摘要：

  制备了N，O-二酰基羟胺衍生物4，并研究了其与亲核试剂的反应性。与环状或无环酮的烯醇锂反应时，4立体选择性地转化为相应的亚烷基苯酞。可以通过改变反应介质的极性和在酸性条件下异构化的产物来改变转化的立体化学结果。

  DOI：

  10.1021/acs.orglett.6b01203

文献信息

• Kinetics of Action of a Two-Stage Pro-Inhibitor of Serine β-Lactamases
  作者：Ronak Tilvawala、R. F. Pratt

  DOI：10.1021/bi400873r

  日期：2013.10.8

  beta-Lactamase inhibitors are important in medicine in the protection of beta-lactam antibiotics from beta-lactamase-catalyzed destruction. The most effective inhibitors of serine beta-lactamases covalently modify the enzyme active site. We have recently studied O-acyl and O-phosphyl hydroxamates as a new class of such inhibitors. In this paper, we describe our studies of the N-acyl derivatives of a cyclic O-acyl hydroxamic acid, 3H-benzo[d][1,2]oxazine-1,4-dione, and, in particular, the N-tert-butoxycarbonyl derivative. This compound is not a beta-lactamase inhibitor itself but undergoes spontaneous hydrolysis in aqueous solution, yielding an O-phthaloyl hydroxamic acid, which is a beta-lactamase inhibitor. This compound spontaneously, but reversibly, cyclizes in solution to form phthalic anhydride, which is also a beta-lactamase inhibitor. Both inhibitors react to form the same transiently stable phthaloyl-enzyme complex. Thus, we have a two-step cascade, beginning with a pro-inhibitor, in which each step leads to a different inhibitor, presumably with different enzyme specificities. The kinetics of these transformations have been elucidated in detail. The phthaloyl derivatives, where the free carboxylate is important for facile reaction with the enzyme, represent a new lead for serine beta-lactamase inhibitors. Analogues can be conveniently constructed in situ by reaction of nucleophiles with phthalic anhydrides and then screened for activity. Active hits may then become new leads.