1-(1,3-benzoxazol-2-yl)-2-[5-chloro-2-(methylsulfonyl)-4-pyrimidinyl]-2-oxoethyl cyanide | 299218-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 1-(1,3-benzoxazol-2-yl)-2-[5-chloro-2-(methylsulfonyl)-4-pyrimidinyl]-2-oxoethyl cyanide
• 英文别名: 2-(1,3-Benzoxazol-2-yl)-3-(5-chloro-2-methylsulfonylpyrimidin-4-yl)-3-oxopropanenitrile
• CAS: 299218-28-3
• 化学式: C₁₅H₉ClN₄O₄S
• 分子量: 376.78
• InChiKey: NSSAFEXXJPYMFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(1,3-benzoxazol-2-yl)-2-[5-chloro-2-(methylsulfonyl)-4-pyrimidinyl]-2-oxoethyl cyanide 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以84%的产率得到3-(methylsulfonyl)-5-oxo-5H-benzo[d]pyrimido[4',5':5,6]pyrido[2,1-b][1,3]oxazole-6-carbonitrile
  参考文献：
  名称：

  Nucleophilic Substitution in Some 5-Chloropyrimidines. Synthesis and Properties of Condensed Pyridopyrimidines

  摘要：

  Reaction of hetarylacetonitriles 1 with 5-chloro-2-(methylsulfonyl)-4-pyrimidinecarbonyl chloride affords a series of new ketonitriles 3e-h. The reactions of compounds 3 with aliphatic amines were studied. In the reaction of 3c, d, g with aliphatic amines the replacement of methylsulfonyl group took place to give products 4. In the reaction of 3a with aliphatic amines 3-(NRR2)-R-1-5-oxo-5H-pyrimido-[4,5-c]quinolizin-6-yl cyanides 5a-d were formed. Compounds 3 cyclized into fused pyridopyrimidines 6-10 in the presence of Et3N and the displacement of methylsulfonyl group in 6, 7, 9 by amines was investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00181-2
• 作为产物：
  描述：

  1,3-苯并噁唑-2-乙腈 、 2-methylsulfonyl-5-chloropyrimidine-4-carboxylic acid chloride 在 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以87%的产率得到1-(1,3-benzoxazol-2-yl)-2-[5-chloro-2-(methylsulfonyl)-4-pyrimidinyl]-2-oxoethyl cyanide
  参考文献：
  名称：

  Nucleophilic Substitution in Some 5-Chloropyrimidines. Synthesis and Properties of Condensed Pyridopyrimidines

  摘要：

  Reaction of hetarylacetonitriles 1 with 5-chloro-2-(methylsulfonyl)-4-pyrimidinecarbonyl chloride affords a series of new ketonitriles 3e-h. The reactions of compounds 3 with aliphatic amines were studied. In the reaction of 3c, d, g with aliphatic amines the replacement of methylsulfonyl group took place to give products 4. In the reaction of 3a with aliphatic amines 3-(NRR2)-R-1-5-oxo-5H-pyrimido-[4,5-c]quinolizin-6-yl cyanides 5a-d were formed. Compounds 3 cyclized into fused pyridopyrimidines 6-10 in the presence of Et3N and the displacement of methylsulfonyl group in 6, 7, 9 by amines was investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00181-2

文献信息

• Nucleophilic Substitution in Some 5-Chloropyrimidines. Synthesis and Properties of Condensed Pyridopyrimidines
  作者：Yulian M. Volovenko、Evgeniy V. Blyumin

  DOI：10.1016/s0040-4020(00)00181-2

  日期：2000.7

  Reaction of hetarylacetonitriles 1 with 5-chloro-2-(methylsulfonyl)-4-pyrimidinecarbonyl chloride affords a series of new ketonitriles 3e-h. The reactions of compounds 3 with aliphatic amines were studied. In the reaction of 3c, d, g with aliphatic amines the replacement of methylsulfonyl group took place to give products 4. In the reaction of 3a with aliphatic amines 3-(NRR2)-R-1-5-oxo-5H-pyrimido-[4,5-c]quinolizin-6-yl cyanides 5a-d were formed. Compounds 3 cyclized into fused pyridopyrimidines 6-10 in the presence of Et3N and the displacement of methylsulfonyl group in 6, 7, 9 by amines was investigated. (C) 2000 Elsevier Science Ltd. All rights reserved.