3-mesityl-3-oxo-propionitrile | 116283-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-mesityl-3-oxo-propionitrile
• 英文别名: 3-Oxo-3-(2.4.6-trimethyl-phenyl)-propionitril；3-Oxo-3-mesityl-propionsaeure-nitril；2,4,6-Trimethyl-beta-oxo-benzenepropanenitrile；3-oxo-3-(2,4,6-trimethylphenyl)propanenitrile
• CAS: 116283-33-1
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: HYAIHHYAUVGHGE-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  344.4±30.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-mesityl-3-oxo-propionitrile 在 盐酸 、 甲醇 作用下， 生成 3-mesityl-3-oxo-propionic acid-[2]pyridylamide
  参考文献：
  名称：

  Certain Azomethines in the Pyrimidazolone Series

  摘要：

  DOI：

  10.1021/ja01239a001
• 作为产物：
  描述：

  (Z)-2-Cyano-3-hydroxy-3-(2,4,6-trimethyl-phenyl)-acrylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以81%的产率得到3-mesityl-3-oxo-propionitrile
  参考文献：
  名称：

  Tyrphostins. II. Heterocyclic and .alpha.-substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2/neu tyrosine kinases

  摘要：

  We have previously described a novel series of low molecular weight protein tyrosine kinase inhibitors which we named tyrphostins. The characteristic active pharmacophore of these compounds was the hydroxy-cis-benzylidenemalononitrile moiety. In this article we describe three novel groups of tyrphostins: (i) one group has the phenolic moiety of the cis-benzylidenemalononitrile replaced either with other substituted benzenes or with heteroaromatic rings, (ii) another is a series of conformationally constrained derivatives of hydroxy-cis-benzylidenemalononitriles in which the malononitrile moiety is fixed relative to the aromatic ring, and (iii) two groups of compounds in which the position trans to the benzenemalononitrile has been substituted by ketones and amides. Among the novel tyrphostins examined we found inhibitors which discriminate between the highly homologous EGF receptor kinase (HER1) and ErbB2/neu kinase (HER2). These findings may lead to selective tyrosine kinase blockers for the treatment of diseases in which ErbB2/neu is involved.

  DOI：

  10.1021/jm00110a022

文献信息

• The Methylation of β-Ketonitriles
  作者：Reynold C. Fuson、Donald E. Wolf

  DOI：10.1021/ja01877a002

  日期：1939.8
• A Plan for Distinguishing between Some Five- and Six-membered Ring Ketones
  作者：William S. Johnson、Wesley E. Shelberg

  DOI：10.1021/ja01226a038

  日期：1945.10
• The Synthesis of Some 6-Substituted-2-thiouracils¹
  作者：Wilbur H. Miller、Alice M. Dessert、George W. Anderson

  DOI：10.1021/ja01182a020

  日期：1948.2
• 2-Carbonyl-3-hydroxy-alkenonitriles, their use as anti-arthritic agents and processes for their preparation
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0016277B1

  公开（公告）日：1981-12-02
• Autoimmune thyroiditis in non-obese subjects with initial diagnosis of Type 2 diabetes mellitus
  作者：M. Matějková-Běhanová、V. Zamrazil、K. Vondra、J. Vrbíková、P. Kučera、M. Hill、M. Anděl

  DOI：10.1007/bf03345512

  日期：2002.10

  Autoimmune thyroiditis is often associated with Type 1 diabetes mellitus (T1DM). In non-obese adult-onset diabetes diagnosed initially as Type 2 diabetes mellitus (T2DM), there is a proportion of cases with so far undiagnosed T1DM. The objective of this study was to estimate the frequency of autoimmune thyroiditis (AT) among non-obese (BMI <30.0 kg/m2) patients with T2DM and to compare the frequency of AT in subgroups of patients according to the presence of glutamic acid decarboxylase antibodies (GADA), insulin requirement, and post-breakfast C-peptide levels. The study included 118 adult patients (55 men and 63 women) with the initial diagnosis of T2DM and age at the onset of diabetes > 35 yr. Median of age was 66 yr (range 39-82), and median duration of diabetes was 9 (range 1-27) yr. AT was diagnosed using thyroid peroxidase antibodies, TG-antibodies, US and TSH levels. Nineteen per cent of the subjects were found to have AT, and the frequency of AT did not significantly differ between the groups of GADA+ and GADA- subjects. There was no difference in the frequency of AT between the group treated with hypoglycemic agents and/or diet and the group requiring insulin. The frequency of AT was higher in the group with post-breakfast C-peptide levels < or = 0.8 nmol/l compared to the group with post-breakfast C-peptide levels > 0.8 nmol/l (37% vs 16%), however the group with post-breakfast C-peptide levels < or = 0.8 nmol/l had longer duration of diabetes.