3,3-二乙基氮杂环丁-2-酮 | 16006-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 3,3-二乙基氮杂环丁-2-酮
• 英文名称: 3,3-Diethyl-azetidin-2-on
• 英文别名: 3,3-Diethylazetidin-2-one
• CAS: 16006-10-3
• 化学式: C₇H₁₃NO
• mdl: MFCD01665381
• 分子量: 127.186
• InChiKey: XHMUOLXEAFNULF-UHFFFAOYSA-N

物化性质

• 沸点：
  91-96 °C(Press: 0.8 Torr)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933790090

反应信息

• 作为反应物：
  描述：

  3,3-二乙基氮杂环丁-2-酮 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 3,3-diethylazetidine
  参考文献：
  名称：

  Testa et al., Justus Liebigs Annalen der Chemie, 1959, vol. 626, p. 121

  摘要：

  DOI：
• 作为产物：
  描述：

  2-吖丁啶酮,4-(乙酰氧基)-3,3-二乙基- 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以28%的产率得到3,3-二乙基氮杂环丁-2-酮
  参考文献：
  名称：

  Design, Synthesis, and Enzymatic Evaluation of N-Acyloxyalkyl- and N¹-Oxazolidin-2,4-dion-5-yl-Substituted β-lactams as Novel Inhibitors of Human Leukocyte Elastase

  摘要：

  Human leukocyte elastase (HLE) is a serine protease that very efficiently degrades various tissue matrix proteins such as elastin. The imbalance between HLE and its endogenous inhibitors leads to excessive elastin proteolysis and is considered to be responsible for the onset of chronic obstructive pulmonary disease (COPD). A novel series of C-3-, C-4-, and N-1-substituted azetidin-2-ones were prepared as potential mechanism-based inhibitors of HLE to restore the protease/antiprotease imbalance. N-Acyloxyalkylazetidin-2-ones, 4, and their carbamate counterparts, 5, are weak HLE inhibitors, being 5 times less active than their bicyclic oxazolidin-2,4-dione-substituted analogues, 6, containing an electron-withdrawing substituent at C-4. Compounds 6 containing a C-4 substituent exist as two diastereomeric pairs of enantiomers, each pair presenting similar inhibitory activity against HLE. Comparative docking experiments with the C-4-substituted oxazolidin-2,4-dione inhibitors 6 suggest that only the 4R,5 ' S and 4S,5'S diastereomers consistently interact with the beta-lactam carbonyl carbon atom accessible to the serine hydroxyl oxygen.

  DOI：

  10.1021/jm0501331

文献信息

• The efficiency of C-4 substituents in activating the β-lactam scaffold towards serine proteases and hydroxide ion
  作者：Jalmira Mulchande、Luísa Martins、Rui Moreira、Margarida Archer、Tania F. Oliveira、Jim Iley

  DOI：10.1039/b706622h

  日期：——

  that second-order rate constants for the alkaline hydrolysis and elastase inactivation by N-carbamoyl monobactams are independent of the pKa of the leaving group at C-4. Indeed, the effect exerted by these substituents is purely inductive: electron-withdrawing substituents at C-4 of N-carbamoyl-3,3-diethylmonobactams increase the rate of alkaline hydrolysis and elastase inactivation, with Hammett pI

  通常认为在单bactams C-4处有一个离去基团是这些酰化剂基于机制抑制人白细胞弹性蛋白酶的必要条件。我们报告说，N-氨基甲酰基单bactams的碱性水解和弹性蛋白酶失活的二级速率常数与C-4上离去基团的pKa无关。实际上，这些取代基发挥的作用纯粹是感应性的：N-氨基甲酰基-3,3-二乙基单bactams C-4处的吸电子取代基可提高碱性水解和弹性蛋白酶的失活速率，哈米特pI值分别为3.4和2.5。 ，表明在过渡态中产生负电荷。当与化学过程相比时，这些pI值之间的大小差异与酶促反应的较早过渡状态一致。这些结果表明，弹性蛋白酶失活的限速步骤是四面体中间体的形成，并且β-内酰胺开环与离去基团离开C-4不协调。即使不存在与主要识别位点相互作用所需的C-3乙基，单bactamulfones仍然是有效的弹性蛋白酶抑制剂。对于一种这样的化合物，已经通过X射线晶体学检查了涉及猪胰弹性蛋白酶的1：1酶抑
• Au-Catalyzed Synthesis of 5,6-Dihydro-8<i>H</i>-indolizin-7-ones from <i>N</i>-(Pent-2-en-4-ynyl)-β-lactams
  作者：Yu Peng、Meng Yu、Liming Zhang

  DOI：10.1021/ol802159v

  日期：2008.11.20

  Au-catalyzed synthesis of 5,6-dihydro-8H-indolizin-7-ones from readily available N-(pent-2-en-4-ynyl)-beta-lactams is developed. In this reaction, a 5-exo-dig cyclization of the beta-lactam nitrogen to the Au-activated C-C triple bond is followed by heterolytic fragmentation of the amide bond, forming a highly nucleophilic acyl cation. An expedient formal synthesis of indolizidine 167B was easily achieved using this new method.
• Testa; Fontanella, Justus Liebigs Annalen der Chemie, 1959, vol. 625, p. 95,97
  作者：Testa、Fontanella

  DOI：——

  日期：——
• [EN] SUBSTITUTED AZETIDINONES AS ANTI-INFLAMMATORY AND ANTIDEGENERATIVE AGENTS
  申请人：MERCK & CO., INC.

  公开号：WO1993000332A1

  公开（公告）日：1993-01-07

  (EN) New substituted azetidinones of general formula (I) which have been found to be potent elastase inhibitors and thereby useful anti-inflammatory and antidegenerative agents are described.(FR) Nouvelles azétidinones substituées de la formule générale (I) dont on a découvert qu'elles constituent des inhibiteurs puissants d'élastase, et par conséquent sont utiles comme agents anti-inflamatoires et antidégénératifs.
• CN117185976
  申请人：——

  公开号：——

  公开（公告）日：——