4-chloro-5-ethylisoxazolo[5,4-d]pyrimidine | 190263-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-chloro-5-ethylisoxazolo[5,4-d]pyrimidine
• 英文别名: 4-Chloro-3-ethylisoxazolo[5,4-d]pyrimidine；4-chloro-3-ethyl-[1,2]oxazolo[5,4-d]pyrimidine
• CAS: 190263-05-9
• 化学式: C₇H₆ClN₃O
• mdl: MFCD14780446
• 分子量: 183.597
• InChiKey: YHSDXFZNFDMMFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-5-ethylisoxazolo[5,4-d]pyrimidine 在 sodium hydride 、 硫脲 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 生成 4-thiocyanato-3-ethylisoxazolo[5,4-d]pyrimidine
  参考文献：
  名称：

  Electrophilic Cyanations. I. Synthesis of Thiocyanatoheteroarenes and Tosylheteroarenes from Mercaptoheteroarenes Using p-Toluenesulfonyl Cyanide

  摘要：

  Mercaptoheteroarenes (1) underwent electrophilic cyanation with p-toluenesulfonyl cyanide (TsCN) in THF in the presence of NaH to give the corresponding thiocyanatoheteroarenes (2) in moderate to good yields. In DMF, tosylheteroarenes (4) were formed by substitution with p-toluenesulfinate ion through thiocyanatoheteroarenes (2).

  DOI：

  10.3987/com-97-7740
• 作为产物：
  描述：

  3-乙基[1,2]恶唑并[5,4-d]嘧啶-4(5H)-酮 在 三氯氧磷 作用下， 反应 2.0h， 生成 4-chloro-5-ethylisoxazolo[5,4-d]pyrimidine
  参考文献：
  名称：

  Aroylation of Fused Pyrimidines; Synthesis of 4-Aroylfuro[2,3-d]-, 4-Aroylthieno[2,3-d]-, and 4-Aroylisoxazolo[5,4-d]pyrimidines

  摘要：

  4-Aroylfuro[2,3-d]-(4), 4-aroylthieno[2,3-d]-(7 and 8), and 4-aroylisoxazolo[5,4-d]pyrimidines (13) were synthesized by aroylation of the fused chloro-(3a and 12) or bromopyrimidines (3b, 5, and 6) with arenecarbaldehydes (2) catalyzed by an imidazolium salt (1a). The fused aroylpyrimidines (4 and 7) were also synthesized by oxidative decyanation of alpha-phenylheteroareneacetonitriles (10 and 11).

  DOI：

  10.3987/com-97-7914

文献信息

• Regioselective synthesis of substituted isoxazolo[5,4-d]pyrimidines
  作者：Sergey B. Alyabiev、Dmitri V. Kravchenko、Alexandre V. Ivachtchenko

  DOI：10.1016/j.mencom.2008.05.011

  日期：2008.5

  A convenient regioselective synthesis of new N- and O-substituted isoxazolo[5,4-d]pyrimidine derivatives is described.