2-amino-3-(dibenzofuran-3-yl)-propionic acid methyl ester | 367942-22-1

• 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: 2-amino-3-(dibenzofuran-3-yl)-propionic acid methyl ester
• 英文别名: methyl (2S)-2-amino-3-dibenzofuran-3-ylpropanoate
• CAS: 367942-22-1
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: NRONJZHBKONRLP-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2-amino-3-(dibenzofuran-3-yl)-propionic acid methyl ester 在 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 hexahydrotriazine 2-[3,5-bis(2-dibenzofuran-3-yl-1-methoxycarbonylethyl)-[1,3,5]triazinan-1-yl]-3-dibenzofuran-3-ylpropionic acid
  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 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 氯仿 、 乙腈 为溶剂， 反应 26.67h， 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

文献信息

• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSES ORGANIQUES
  申请人：NOVARTIS AG

  公开号：WO2001077095A2

  公开（公告）日：2001-10-18

  Novel thiol derivatives of formula (I) wherein variables R1, R2, R3, R4, A, X, and Y have the meanings as defined hereinbefore; disulfide derivatives derived from said compounds wherein R1 is hydrogen; and pharmaceutically acceptable salts thereof; said compounds being useful as endothelin converting enzyme inhibitors.
• 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.