(1R,4R,5R)-1,5-dimethyl-4-hydroxy-10-oxa-bicyclo[4.3.1]dec-6-ene-7-carboxylic acid methyl ester | 1370458-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,4R,5R)-1,5-dimethyl-4-hydroxy-10-oxa-bicyclo[4.3.1]dec-6-ene-7-carboxylic acid methyl ester
• CAS: 1370458-34-6
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: FAORTRLDRRRQDT-ZDSQKVDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,4R,5R)-1,5-dimethyl-4-hydroxy-10-oxa-bicyclo[4.3.1]dec-6-ene-7-carboxylic acid methyl ester 在 potassium trimethylsilonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以2.8 mg的产率得到(-)-(R)-2-ethyl-6-(2-formylethyl)-5,6-dihydro-6-methyl-4H-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric and Highly Stereoselective Synthesis of the DEF-Ring Moiety of (−)-FR182877 and Its Derivative Inducing Mitotic Arrest

  摘要：

  The asymmetric and highly stereoselective synthesis of compound 1, which corresponds exactly to the DEF-ring moiety of (-)-FR182877, and the biological activities of its derivatives are described. All derivatives of 1 showed no activity in the tubulin polymerization assay, but one derivative was shown to have the ability to induce mitotic arrest by interfering with microtubule dynamics, and the cellular effects are similar to those of paclitaxel.

  DOI：

  10.1021/ol300615w
• 作为产物：
  描述：

  4-甲基-4-戊烯醛 在 咪唑 、 六甲基磷酰三胺 、 2,6-二叔丁基-4-甲基苯酚 、 三氟甲磺酸二丁硼 、 四丁基氟化铵 、 三甲基铝 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 122.17h， 生成 (1R,4R,5R)-1,5-dimethyl-4-hydroxy-10-oxa-bicyclo[4.3.1]dec-6-ene-7-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric and Highly Stereoselective Synthesis of the DEF-Ring Moiety of (−)-FR182877 and Its Derivative Inducing Mitotic Arrest

  摘要：

  The asymmetric and highly stereoselective synthesis of compound 1, which corresponds exactly to the DEF-ring moiety of (-)-FR182877, and the biological activities of its derivatives are described. All derivatives of 1 showed no activity in the tubulin polymerization assay, but one derivative was shown to have the ability to induce mitotic arrest by interfering with microtubule dynamics, and the cellular effects are similar to those of paclitaxel.

  DOI：

  10.1021/ol300615w