(-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]-acrylic acid methyl ester | 1370458-31-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]-acrylic acid methyl ester
• 英文别名: methyl (4S,5S)-3-hydroxy-4,8-dimethyl-2-methylidene-5-triethylsilyloxynon-8-enoate
• CAS: 1370458-31-3
• 化学式: C₁₉H₃₆O₄Si
• 分子量: 356.578
• InChiKey: DWCSQEUCSSEGQA-OEQNEYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]-acrylic acid methyl ester 在 盐酸 、 Otera's catalyst 、 2,6-二叔丁基-4-甲基苯酚 、 2-氯-1-甲基吡啶碘化物 、 水 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 143.17h， 生成 (-)-(2R,4aR,7S,8R,8aR)-2,7-ethano-2,8-dimethyl-8a-methoxyhexahydropyrano[4.3-b]pyran-5(7H)-one
  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 、 三氟甲磺酸二丁硼 、 三甲基铝 、 二异丁基氢化铝 、 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 17.17h， 生成 (-)-2-[(2S,3S)-2,6-dimethyl-1-hydroxy-3-triethylsilanyloxyhepta-6-enyl]-acrylic 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

文献信息

• Asymmetric and Highly Stereoselective Synthesis of the DEF-Ring Moiety of (−)-FR182877 and Its Derivative Inducing Mitotic Arrest
  作者：Yu Kobayakawa、Yusuke Mori、Hideki Okajima、Yasuhiko Terada、Masahisa Nakada

  DOI：10.1021/ol300615w

  日期：2012.4.20

  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.