2-((E)-4-Hydroxy-2-triethylsilanyl-but-2-enyl)-malonic acid tert-butyl ester methyl ester | 816417-16-0

• 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-((E)-4-Hydroxy-2-triethylsilanyl-but-2-enyl)-malonic acid tert-butyl ester methyl ester
• 英文别名: 3-O-tert-butyl 1-O-methyl 2-[(E)-4-hydroxy-2-triethylsilylbut-2-enyl]propanedioate
• CAS: 816417-16-0
• 化学式: C₁₈H₃₄O₅Si
• 分子量: 358.55
• InChiKey: IJSKRIIKEALJPD-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((E)-4-Hydroxy-2-triethylsilanyl-but-2-enyl)-malonic acid tert-butyl ester methyl ester 在 potassium tert-butylate 、 间氯过氧苯甲酸 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (1S,5S)-5-Triethylsilanyl-6-oxa-bicyclo[3.1.0]hex-2-ene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A stereoselective synthesis of silylated epoxycyclopentanols bearing four contiguous stereogenic centers

  摘要：

  A palladium-catalyzed Tsuji-Trost alkylation of (E)-2-triethylsilyl-1,4-diacetoxy-but-2-ene with tert-butyl methyl malonate has been performed in excellent chemo and stereoselectivities. The allylated product has been further transformed in few steps in silylated epoxycyclopentanols bearing four controlled stereogenic carbons. The key reaction is a mild tandem oxidation-aldolization induced by DMP or IBX reagents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.017
• 作为产物：
  描述：

  2-((E)-4-Acetoxy-2-triethylsilanyl-but-2-enyl)-malonic acid tert-butyl ester methyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-((E)-4-Hydroxy-2-triethylsilanyl-but-2-enyl)-malonic acid tert-butyl ester methyl ester
  参考文献：
  名称：

  A stereoselective synthesis of silylated epoxycyclopentanols bearing four contiguous stereogenic centers

  摘要：

  A palladium-catalyzed Tsuji-Trost alkylation of (E)-2-triethylsilyl-1,4-diacetoxy-but-2-ene with tert-butyl methyl malonate has been performed in excellent chemo and stereoselectivities. The allylated product has been further transformed in few steps in silylated epoxycyclopentanols bearing four controlled stereogenic carbons. The key reaction is a mild tandem oxidation-aldolization induced by DMP or IBX reagents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.017