dimethyl (4R)-3-hydroxy-3-(hydroxymethyl)-4-vinylcyclopentane-1,1-dicarboxylate | 943248-08-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: dimethyl (4R)-3-hydroxy-3-(hydroxymethyl)-4-vinylcyclopentane-1,1-dicarboxylate
• CAS: 943248-08-6
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: VFUCHHSHKXPFTG-KBPLZSHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl (4R)-3-hydroxy-3-(hydroxymethyl)-4-vinylcyclopentane-1,1-dicarboxylate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以100%的产率得到dimethyl (4S)-4-ethyl-3-hydroxy-3-(hydroxymethyl)cyclopentane-1,1-dicarboxylate
  参考文献：
  名称：

  Palladium-catalyzed intra-molecular olefin insertion reaction of α-alkenyl-α-acyloxytrialkylsilane. Synthesis of optically active carbocycle

  摘要：

  Pd-catalyzed intra-molecular olefin insertion/carbonylation reaction of optically active alpha-alkenyl-alpha-acyloxysilanes is described. The reactions proceeded in a stereoselective manner to give five- and six-membered optically active carbocycles having (E)-vinylsilane in their side chains. Under CO condition, optically active carbocycles containing one-carbon homologated side chain were produced by Pd-catalyzed tandem olefin insertion-carbonylation reaction. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.029
• 作为产物：
  描述：

  dimethyl (3R)-3-[(E)-2-[tert-butyl(dimethyl)silyl]ethenyl]-4-methylidenecyclopentane-1,1-dicarboxylate 在 四氧化锇 、 N-甲基吲哚酮 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 dimethyl (4R)-3-hydroxy-3-(hydroxymethyl)-4-vinylcyclopentane-1,1-dicarboxylate
  参考文献：
  名称：

  Palladium-catalyzed intra-molecular olefin insertion reaction of α-alkenyl-α-acyloxytrialkylsilane. Synthesis of optically active carbocycle

  摘要：

  Pd-catalyzed intra-molecular olefin insertion/carbonylation reaction of optically active alpha-alkenyl-alpha-acyloxysilanes is described. The reactions proceeded in a stereoselective manner to give five- and six-membered optically active carbocycles having (E)-vinylsilane in their side chains. Under CO condition, optically active carbocycles containing one-carbon homologated side chain were produced by Pd-catalyzed tandem olefin insertion-carbonylation reaction. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.029