(E)-2-[1-methyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)allyl]malonic acid dimethyl ester | 1313878-04-4

• 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: (E)-2-[1-methyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)allyl]malonic acid dimethyl ester
• 英文别名: dimethyl 2-[(E)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-3-en-2-yl]propanedioate
• CAS: 1313878-04-4
• 化学式: C₁₅H₂₅BO₆
• 分子量: 312.171
• InChiKey: JYWSSJYCJHBCHP-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-2-[1-methyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)allyl]malonic acid dimethyl ester 在 sodium azide 、 copper(II) sulfate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以78%的产率得到(E)-2-(3-azido-1-methyl-allyl)malonic acid dimethyl ester
  参考文献：
  名称：

  Achieving Chemo-, Regio-, and Stereoselectivity in Palladium-Catalyzed Reaction of γ-Borylated Allylic Acetates

  摘要：

  Three-carbon highly functionalized gamma-borylated allylic acetates underwent a regio- and stereocontrolled Tsuji-Trost reaction in the presence of palladium complexes. An Ipso substitution of the acetate with complete stereoretention of the chiral center was achieved, leading to vinylic boronates with enantiomeric excesses above 99%.

  DOI：

  10.1021/ol201661s
• 作为产物：
  描述：

  丙二酸二甲酯 在 palladium diacetate 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 mineral oil 为溶剂， 生成 (E)-2-[1-methyl-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)allyl]malonic acid dimethyl ester
  参考文献：
  名称：

  Achieving Chemo-, Regio-, and Stereoselectivity in Palladium-Catalyzed Reaction of γ-Borylated Allylic Acetates

  摘要：

  Three-carbon highly functionalized gamma-borylated allylic acetates underwent a regio- and stereocontrolled Tsuji-Trost reaction in the presence of palladium complexes. An Ipso substitution of the acetate with complete stereoretention of the chiral center was achieved, leading to vinylic boronates with enantiomeric excesses above 99%.

  DOI：

  10.1021/ol201661s

文献信息

• Achieving Chemo-, Regio-, and Stereoselectivity in Palladium-Catalyzed Reaction of γ-Borylated Allylic Acetates
  作者：Krishna Kishore Kukkadapu、Aziz Ouach、Pedro Lozano、Michel Vaultier、Mathieu Pucheault

  DOI：10.1021/ol201661s

  日期：2011.8.5

  Three-carbon highly functionalized gamma-borylated allylic acetates underwent a regio- and stereocontrolled Tsuji-Trost reaction in the presence of palladium complexes. An Ipso substitution of the acetate with complete stereoretention of the chiral center was achieved, leading to vinylic boronates with enantiomeric excesses above 99%.