(R)-3-Triisopropylsilanyloxy-hex-5-enoic acid ethyl ester | 1057657-78-9

• 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: (R)-3-Triisopropylsilanyloxy-hex-5-enoic acid ethyl ester
• CAS: 1057657-78-9
• 化学式: C₁₇H₃₄O₃Si
• 分子量: 314.541
• InChiKey: KTQWCLWKGZVVFP-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  21.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (R)-3-Triisopropylsilanyloxy-hex-5-enoic acid ethyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-3-Triisopropylsilanyloxy-hex-5-enal
  参考文献：
  名称：

  Concise Total Synthesis of (+)-Brefeldin A:  A Combined β-Lactone/Cross-Metathesis-Based Strategy

  摘要：

  A highly convergent total synthesis of (+)-brefeldin A that relies on a diastereoselective, beta-lactone-based cyclopentane synthesis combined with complex cross-metathesis reactions is described. The utility of beta-lactones for natural product synthesis and the versatility of cross-metathesis in this context were demonstrated, including the tolerance of an epimerizable aldehyde and a beta-lactone.

  DOI：

  10.1021/ol026438g
• 作为产物：
  描述：

  三异丙基硅基三氟甲磺酸酯 在 六甲基磷酰三胺 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (R)-3-Triisopropylsilanyloxy-hex-5-enoic acid ethyl ester
  参考文献：
  名称：

  Concise Total Synthesis of (+)-Brefeldin A:  A Combined β-Lactone/Cross-Metathesis-Based Strategy

  摘要：

  A highly convergent total synthesis of (+)-brefeldin A that relies on a diastereoselective, beta-lactone-based cyclopentane synthesis combined with complex cross-metathesis reactions is described. The utility of beta-lactones for natural product synthesis and the versatility of cross-metathesis in this context were demonstrated, including the tolerance of an epimerizable aldehyde and a beta-lactone.

  DOI：

  10.1021/ol026438g

文献信息

• A Sequential Two‐Component Etherification/Oxa‐Conjugate Addition Reaction: Asymmetric Synthesis of (+)‐Leucascandrolide A Macrolactone
  作者：P. Andrew Evans、William J. Andrews

  DOI：10.1002/anie.200801357

  日期：2008.7.7