2,5-di((S)-sec-butyl)-3-chloropyrazine | 1429637-78-4

• 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: 2,5-di((S)-sec-butyl)-3-chloropyrazine
• 英文别名: 2,5-bis[(2S)-butan-2-yl]-3-chloropyrazine
• CAS: 1429637-78-4
• 化学式: C₁₂H₁₉ClN₂
• 分子量: 226.749
• InChiKey: MCTAFUUCPZHXMN-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-di((S)-sec-butyl)-3-chloropyrazine 在 双氧水 、 间氯过氧苯甲酸 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,5-di((S)-sec-butyl)-3,6-bis(2-(trimethylsilyl)ethoxy)pyrazine 1,4-dioxide
  参考文献：
  名称：

  Convergent Synthesis and Structural Confirmation of Phellodonin and Sarcodonin ε

  摘要：

  The first synthesis of members of the sarcodonin family, phellodonin and sarcodonin epsilon, is reported herein. This verifies that the unprecedented and seemingly unstable N,N-dioxide-containing benzodioxazine framework can be constructed in the laboratory and lends further support to the proposed structures. The key step in the synthesis involves a biomimetic hetero-Diels-Alder reaction between a pyrazine N-oxide and an ortho-quinone.

  DOI：

  10.1021/ol400709f
• 作为产物：
  描述：

  L-异亮氨酸 在 三氯氧磷 作用下， 以 乙二醇 为溶剂， 反应 30.0h， 生成 2,5-di((S)-sec-butyl)-3-chloropyrazine
  参考文献：
  名称：

  Convergent Synthesis and Structural Confirmation of Phellodonin and Sarcodonin ε

  摘要：

  The first synthesis of members of the sarcodonin family, phellodonin and sarcodonin epsilon, is reported herein. This verifies that the unprecedented and seemingly unstable N,N-dioxide-containing benzodioxazine framework can be constructed in the laboratory and lends further support to the proposed structures. The key step in the synthesis involves a biomimetic hetero-Diels-Alder reaction between a pyrazine N-oxide and an ortho-quinone.

  DOI：

  10.1021/ol400709f

文献信息

• Convergent Synthesis and Structural Confirmation of Phellodonin and Sarcodonin ε
  作者：Ippei Usui、David W. Lin、Takeshi Masuda、Phil S. Baran

  DOI：10.1021/ol400709f

  日期：2013.5.3

  The first synthesis of members of the sarcodonin family, phellodonin and sarcodonin epsilon, is reported herein. This verifies that the unprecedented and seemingly unstable N,N-dioxide-containing benzodioxazine framework can be constructed in the laboratory and lends further support to the proposed structures. The key step in the synthesis involves a biomimetic hetero-Diels-Alder reaction between a pyrazine N-oxide and an ortho-quinone.