(2S,5R)-2-(dibenzofuran-3-ylmethyl)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine | 693228-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (2S,5R)-2-(dibenzofuran-3-ylmethyl)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine
• CAS: 693228-09-0
• 化学式: C₂₂H₂₄N₂O₃
• 分子量: 364.444
• InChiKey: VWADYEQJCVPSAI-FXAWDEMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5R)-2-(dibenzofuran-3-ylmethyl)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine 在 三氟乙酸 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 2-amino-3-(dibenzofuran-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  A Concise, High Yield Synthesis of the Selective ECE‐Inhibitor, CGS 35066

  摘要：

  A highly efficient synthesis of the selective endothelin-converting enzyme, CGS 35066 is described. The key steps involved a Pd-catalyzed coupling of the phenyl rings of a diphenyl ether, and the use of the Schollkopf reagent, (2R)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine as a chiral auxiliary furnishing a dibenzofuranylmethyl substituted amino ester in high (>98%) enantiomeric purity, which was then carried forward to complete the synthesis of the ECE inhibitor CGS 35066.

  DOI：

  10.1081/scc-120028350
• 作为产物：
  描述：

  3-苯氧基苄基乙酸酯 在 palladium diacetate 、 lithium hydroxide 、 正丁基锂 、 氢溴酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 氯仿 为溶剂， 反应 21.67h， 生成 (2S,5R)-2-(dibenzofuran-3-ylmethyl)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazine
  参考文献：
  名称：

  A Concise, High Yield Synthesis of the Selective ECE‐Inhibitor, CGS 35066

  摘要：

  A highly efficient synthesis of the selective endothelin-converting enzyme, CGS 35066 is described. The key steps involved a Pd-catalyzed coupling of the phenyl rings of a diphenyl ether, and the use of the Schollkopf reagent, (2R)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine as a chiral auxiliary furnishing a dibenzofuranylmethyl substituted amino ester in high (>98%) enantiomeric purity, which was then carried forward to complete the synthesis of the ECE inhibitor CGS 35066.

  DOI：

  10.1081/scc-120028350

文献信息

• A Concise, High Yield Synthesis of the Selective ECE‐Inhibitor, CGS 35066
  作者：Abdul H. Fauq、Murad A. Khan、Christopher Eckman

  DOI：10.1081/scc-120028350

  日期：2004.12.31

  A highly efficient synthesis of the selective endothelin-converting enzyme, CGS 35066 is described. The key steps involved a Pd-catalyzed coupling of the phenyl rings of a diphenyl ether, and the use of the Schollkopf reagent, (2R)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine as a chiral auxiliary furnishing a dibenzofuranylmethyl substituted amino ester in high (>98%) enantiomeric purity, which was then carried forward to complete the synthesis of the ECE inhibitor CGS 35066.