2-((1S,2R)-1,2-Dimethyl-4-trimethylsilanyl-but-3-ynyl)-malonic acid diethyl ester | 378250-87-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-((1S,2R)-1,2-Dimethyl-4-trimethylsilanyl-but-3-ynyl)-malonic acid diethyl ester
• 英文别名: diethyl 2-[(2S,3R)-3-methyl-5-trimethylsilylpent-4-yn-2-yl]propanedioate
• CAS: 378250-87-4
• 化学式: C₁₆H₂₈O₄Si
• 分子量: 312.481
• InChiKey: KUAGAKNQUZDTPJ-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((1S,2R)-1,2-Dimethyl-4-trimethylsilanyl-but-3-ynyl)-malonic acid diethyl ester 在 盐酸 作用下， 反应 2.0h， 以85%的产率得到(2R,3R)-2,3-dimethylpentanedioic acid
  参考文献：
  名称：

  Highly Stereoselective Asymmetric Construction of an Acyclic Carbon Skeleton Having Two Adjacent Alkyl Substituents by Michael Addition of Optically Active Allenyltitaniums to Alkylidenemalonates

  摘要：

  [GRAPHICS]Enantio-enriched allenyltitaniums prepared in situ by the reaction of optically active secondary propargyl phosphates with a divalent titanium reagent Ti(O-i-Pr)(4)/2i-PrMgCl react readily with alkylidenemalonates with excellent regio- and diastereoselectivities to afford the Michael addition products with a high optical purity, thus opening up a new asymmetric method for construction of an acyclic carbon skeleton bearing two adjacent alkyl substituents.

  DOI：

  10.1021/ol016652p
• 作为产物：
  描述：

  亚乙基丙二酸二乙酯 、 diethyl (S)-1-trimethylsilyl-1-butyn-3-yl phosphate 在 titanium(IV) isopropylate 、 异丙基氯化镁 作用下， 以 乙醚 为溶剂， 生成 、 2-((1S,2R)-1,2-Dimethyl-4-trimethylsilanyl-but-3-ynyl)-malonic acid diethyl ester
  参考文献：
  名称：

  Highly Stereoselective Asymmetric Construction of an Acyclic Carbon Skeleton Having Two Adjacent Alkyl Substituents by Michael Addition of Optically Active Allenyltitaniums to Alkylidenemalonates

  摘要：

  [GRAPHICS]Enantio-enriched allenyltitaniums prepared in situ by the reaction of optically active secondary propargyl phosphates with a divalent titanium reagent Ti(O-i-Pr)(4)/2i-PrMgCl react readily with alkylidenemalonates with excellent regio- and diastereoselectivities to afford the Michael addition products with a high optical purity, thus opening up a new asymmetric method for construction of an acyclic carbon skeleton bearing two adjacent alkyl substituents.

  DOI：

  10.1021/ol016652p

文献信息

• Highly Stereoselective Asymmetric Construction of an Acyclic Carbon Skeleton Having Two Adjacent Alkyl Substituents by Michael Addition of Optically Active Allenyltitaniums to Alkylidenemalonates
  作者：Yongcheng Song、Sentaro Okamoto、Fumie Sato

  DOI：10.1021/ol016652p

  日期：2001.11.1

  [GRAPHICS]Enantio-enriched allenyltitaniums prepared in situ by the reaction of optically active secondary propargyl phosphates with a divalent titanium reagent Ti(O-i-Pr)(4)/2i-PrMgCl react readily with alkylidenemalonates with excellent regio- and diastereoselectivities to afford the Michael addition products with a high optical purity, thus opening up a new asymmetric method for construction of an acyclic carbon skeleton bearing two adjacent alkyl substituents.