2,4-dimethylbenzyl isocyanate | 56651-59-3

• 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: 2,4-dimethylbenzyl isocyanate
• 英文别名: 2,4-Dimethyl-benzylisocyanat；1-(isocyanatomethyl)-2,4-dimethylbenzene
• CAS: 56651-59-3
• 化学式: C₁₀H₁₁NO
• mdl: MFCD21880248
• 分子量: 161.203
• InChiKey: ATLVTMVEYQOHCH-UHFFFAOYSA-N

物化性质

• 沸点：
  115-117 °C(Press: 9 Torr)
• 密度：
  1.0402 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dimethylbenzyl isocyanate 在 4-二甲氨基吡啶 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 4-[1-(2,4-Dimethyl-benzylcarbamoyl)-3,3-diethyl-4-oxo-azetidin-2-yloxy]-benzoic acid
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003
• 作为产物：
  描述：

  (2,4-dimethyl-phenyl)-acetyl chloride 在 sodium azide 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 1.0h， 生成 2,4-dimethylbenzyl isocyanate
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003

文献信息

• Chemistry of Isocyanic Acid. I. Reactions of Isocyanic Acid with Carbonyl Compounds
  作者：F. W. Hoover、H. B. Stevenson、H. S. Rothrock

  DOI：10.1021/jo01042a020

  日期：1963.7
• Kozhushko, B. N.; Lomakina, A. V.; Paliichuk, Yu. A., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 654 - 660
  作者：Kozhushko, B. N.、Lomakina, A. V.、Paliichuk, Yu. A.、Shokol, V. A.

  DOI：——

  日期：——
• KOZHUSHKO, B. N.;LOMAKINA, A. V.;PALIJCHUK, YU. A.;SHOKOL, V. A., ZH. ORGAN. XIMII, 1984, 20, N 4, 721-727
  作者：KOZHUSHKO, B. N.、LOMAKINA, A. V.、PALIJCHUK, YU. A.、SHOKOL, V. A.

  DOI：——

  日期：——