(S)-but-3-en-2-yl acetoacetate | 1037025-53-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (S)-but-3-en-2-yl acetoacetate
• 英文别名: [(2S)-but-3-en-2-yl] 3-oxobutanoate
• CAS: 1037025-53-8
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: CVWKTKTYWDIBJV-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-but-3-en-2-yl acetoacetate 在 磺酰氯 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 (S)-but-3-en-2-yl 2-chloroacetoacetate
  参考文献：
  名称：

  Enantiopure furo[3,4-c]pyrazole derivatives by intramolecular nitrilimine cycloaddition: a stereoselectivity rationale based upon MP2 calculations

  摘要：

  Silver carbonate treatment of hydrazonoyl chloride 4 promoted the in situ generation of the corresponding nitrilimine bearing a stereocentre at the alpha-position of the ethylenic dipolarophile. Intramolecular cycloaddition of the latter intermediate involves the formation of 4-(S)-methyl-6-oxo-3,3a,4,5-tetra hydro-furo[3,4-c]pyrazole derivatives with very good yield and diastereoselectivity. Full rationalization of the experimentally observed stereoselectivity has been pursued by means of MP2 calculations. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.007
• 作为产物：
  描述：

  (2S)-丁-3-烯-2-醇 、 2,2,6-三甲基-4H-1,3-二英-4-酮 以 xylene 为溶剂， 反应 1.5h， 以93%的产率得到(S)-but-3-en-2-yl acetoacetate
  参考文献：
  名称：

  Enantiopure furo[3,4-c]pyrazole derivatives by intramolecular nitrilimine cycloaddition: a stereoselectivity rationale based upon MP2 calculations

  摘要：

  Silver carbonate treatment of hydrazonoyl chloride 4 promoted the in situ generation of the corresponding nitrilimine bearing a stereocentre at the alpha-position of the ethylenic dipolarophile. Intramolecular cycloaddition of the latter intermediate involves the formation of 4-(S)-methyl-6-oxo-3,3a,4,5-tetra hydro-furo[3,4-c]pyrazole derivatives with very good yield and diastereoselectivity. Full rationalization of the experimentally observed stereoselectivity has been pursued by means of MP2 calculations. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.007

文献信息

• Enantiopure furo[3,4-c]pyrazole derivatives by intramolecular nitrilimine cycloaddition: a stereoselectivity rationale based upon MP2 calculations
  作者：Giorgio Molteni、Alessandro Ponti

  DOI：10.1016/j.tetasy.2008.05.007

  日期：2008.6

  Silver carbonate treatment of hydrazonoyl chloride 4 promoted the in situ generation of the corresponding nitrilimine bearing a stereocentre at the alpha-position of the ethylenic dipolarophile. Intramolecular cycloaddition of the latter intermediate involves the formation of 4-(S)-methyl-6-oxo-3,3a,4,5-tetra hydro-furo[3,4-c]pyrazole derivatives with very good yield and diastereoselectivity. Full rationalization of the experimentally observed stereoselectivity has been pursued by means of MP2 calculations. (C) 2008 Elsevier Ltd. All rights reserved.