tert-butyl N-[1,3-dioxo-1,3-bis(2-oxopropylamino)propan-2-yl]carbamate | 500109-32-0

• 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: tert-butyl N-[1,3-dioxo-1,3-bis(2-oxopropylamino)propan-2-yl]carbamate
• CAS: 500109-32-0
• 化学式: C₁₄H₂₃N₃O₆
• 分子量: 329.353
• InChiKey: JXWPJJUNCTZEAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[1,3-dioxo-1,3-bis(2-oxopropylamino)propan-2-yl]carbamate 在 palladium on activated charcoal 盐酸 、 氢气 、 magnesium ethylate 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 、 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 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到tert-butyl N-[1,3-dioxo-1,3-bis(2-oxopropylamino)propan-2-yl]carbamate
  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.