(R)-4-[(E)-4-tert-Butoxycarbonylamino-3-oxo-4-(2-oxo-propylcarbamoyl)-but-1-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester | 500109-20-6

• 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: (R)-4-[(E)-4-tert-Butoxycarbonylamino-3-oxo-4-(2-oxo-propylcarbamoyl)-but-1-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
• 英文别名: benzyl (4R)-2,2-dimethyl-4-[(E)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3,5-dioxo-5-(2-oxopropylamino)pent-1-enyl]-1,3-oxazolidine-3-carboxylate
• CAS: 500109-20-6
• 化学式: C₂₆H₃₅N₃O₈
• 分子量: 517.579
• InChiKey: UBNAAHZADAPUCC-PGBQASKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-4-[(E)-4-tert-Butoxycarbonylamino-3-oxo-4-(2-oxo-propylcarbamoyl)-but-1-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 [(R)-1-Aza-bicyclo[3.1.0]hex-(2E)-ylidene-(2-oxo-propylcarbamoyl)-methyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Concise route to α-acylamino-β-keto amides: application to the synthesis of a simplified azinomycin A analogue

  摘要：

  Condensation of acid chlorides (alkyl, aryl or heteroaryl) with N,N'-dialkyl alpha-acylamino malonamides in the presence of magnesium ethoxide provides a direct route to alpha-acylamino-beta-keto amides in moderate to good yields (46-95%). Using this method, a concise route to an enantiomerically enriched 1-azabicyclo[3.1.0]hexane containing most of the elements of the 'right-hand' domain of azinomycin A has been developed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02420-6
• 作为产物：
  描述：

  [Bis-(2-hydroxy-propylcarbamoyl)-methyl]-carbamic acid tert-butyl ester 在 草酰氯 、 magnesium ethylate 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (R)-4-[(E)-4-tert-Butoxycarbonylamino-3-oxo-4-(2-oxo-propylcarbamoyl)-but-1-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
  参考文献：
  名称：

  Concise route to α-acylamino-β-keto amides: application to the synthesis of a simplified azinomycin A analogue

  摘要：

  Condensation of acid chlorides (alkyl, aryl or heteroaryl) with N,N'-dialkyl alpha-acylamino malonamides in the presence of magnesium ethoxide provides a direct route to alpha-acylamino-beta-keto amides in moderate to good yields (46-95%). Using this method, a concise route to an enantiomerically enriched 1-azabicyclo[3.1.0]hexane containing most of the elements of the 'right-hand' domain of azinomycin A has been developed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02420-6

文献信息

• Concise route to α-acylamino-β-keto amides: application to the synthesis of a simplified azinomycin A analogue
  作者：Jean-Yves Goujon、Michael Shipman

  DOI：10.1016/s0040-4039(02)02420-6

  日期：2002.12

  Condensation of acid chlorides (alkyl, aryl or heteroaryl) with N,N'-dialkyl alpha-acylamino malonamides in the presence of magnesium ethoxide provides a direct route to alpha-acylamino-beta-keto amides in moderate to good yields (46-95%). Using this method, a concise route to an enantiomerically enriched 1-azabicyclo[3.1.0]hexane containing most of the elements of the 'right-hand' domain of azinomycin A has been developed. (C) 2002 Elsevier Science Ltd. All rights reserved.