α-benzylprolinamide | 133230-51-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: α-benzylprolinamide
• 英文别名: 2-Benzylpyrrolidine-2-carboxamide
• CAS: 133230-51-0
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: IEPQMGVXXMUGQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(trifluoroacetyl)-α-(3-hydroxy-n-propyl)phenylalaninamide 在 barium dihydroxide 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 生成 α-benzylprolinamide
  参考文献：
  名称：

  Synthesis of .alpha.-benzyl .gamma.-lactam, .alpha.-benzyl .delta.-lactam, and .alpha.-benzylproline derivatives as conformationally restricted analogs of phenylalaninamide

  摘要：

  The ready availability of N-(trifluoroacetyl)-alpha-allylphenylalaninamide (4) via a dehydration/hetero-Cope rearrangement/ammonolysis sequence starting with N-(trifluoroacetyl)phenylalanine allyl ester made it an attractive intermediate for elaboration into C-alpha to N- or C-alpha to N'bridged products as conformationally restricted phenylalaninamide analogues. Oxidative one-carbon degradation of the side-chain olefin followed by acid-catalyzed silane reduction afforded C-alpha to N'-bridged gamma-lactam. Hydroboration/oxidation of the side-chain olefin provided an intermediate that could be cyclized selectively either to a delta-lactam or a proline analogue depending on choice of dehydrating conditions. For preparation of a target dipeptide containing the alpha-substituted proline moiety, a preferred route involved N-deprotection of 4 and coupling to Boc-Asp(OBn)-OH to give a dipeptide intermediate, which similarly could be elaborated selectively to either the alpha-benzyl delta-lactam analogue or the alpha-benzylproline analogue.

  DOI：

  10.1021/jo00012a022

文献信息

• 2-Carboxamide Cycloamino Ureas
  申请人：FAIRHURST Robin Alec

  公开号：US20110003786A1

  公开（公告）日：2011-01-06

  The present invention relates to compounds of formula I and salts thereof, wherein the substituents are as defined in the description, to compositions and use of the compounds in the treatment of diseases ameloriated by inhibition of phosphatidylinositol 3-kinase.

  本发明涉及公式I的化合物及其盐，其中取代基如描述中所定义，以及该化合物在治疗通过抑制磷脂酰肌醇3-激酶改善的疾病中的应用。
• Organic Compounds
  申请人：Caravatti Giorgio

  公开号：US20090163469A1

  公开（公告）日：2009-06-25

  The present invention relates to compounds of formula I and its salts, wherein the substituents are as defined in the description, to compositions and use of the compounds in the treatment of diseases ameloriated by inhibition of phosphatidylinositol 3-kinase.

  本发明涉及公式I的化合物及其盐，其中取代基如描述中所定义，以及该化合物在治疗通过抑制磷脂酰肌醇3-激酶改善的疾病中的应用。
• HOLLADAY, M. W.;NADZAN, A. M., J. ORG. CHEM., 56,(1991) N2, C. 3900-3905
  作者：HOLLADAY, M. W.、NADZAN, A. M.

  DOI：——

  日期：——
• THIAZOLE DERIVATIVES USED AS PI 3 KINASE INHIBITORS
  申请人：Novartis AG

  公开号：EP2240475B1

  公开（公告）日：2013-09-25
• 2-CARBOXAMIDE CYCLOAMINO UREAS USEFUL AS PI3K INHIBITORS
  申请人：Novartis AG

  公开号：EP2448946A1

  公开（公告）日：2012-05-09