(Z)-(S)-3,8-Dihydroxy-6-iodo-oct-5-en-2-one | 477192-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(S)-3,8-Dihydroxy-6-iodo-oct-5-en-2-one
• CAS: 477192-60-2
• 化学式: C₈H₁₃IO₃
• 分子量: 284.094
• InChiKey: KBCGBAGRUHHILP-CDETVPHDSA-N

物化性质

• 沸点：
  406.2±45.0 °C(Predicted)
• 密度：
  1.718±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-(S)-3,8-Dihydroxy-6-iodo-oct-5-en-2-one 在 吡啶 、 咪唑 、 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 [(3Z,6S,7E)-3-iodo-7-methyl-8-(2-methyl-1,3-thiazol-4-yl)-6-triethylsilyloxyocta-3,7-dienyl] 2,2,2-trichloroethyl carbonate
  参考文献：
  名称：

  Probing the SAR of dEpoB via Chemical Synthesis:  A Total Synthesis Evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B

  摘要：

  A practical total synthesis of 26-(1,3-dioxolanyl)-12,13-desoxyepothilone B (26-dioxolanyl dEpoB) was accomplished in a highly convergent manner. A novel sequence was developed to produce the vinyl iodide segment 17 in high enantiomeric excess, which was used in a key B-alkyl Suzuki merger. Subsequently, a Yamaguchi macrocyclization formed the core lactone, while a selective oxidation and a late stage Noyori acetalization incorporated the dioxolane functionality. Sufficient amounts of synthetic 26-dioxolane dEpoB were produced using this sequence for an in vivo analysis in mice containing xenograft CCRF-CEM tumors.

  DOI：

  10.1021/jo020180q
• 作为产物：
  描述：

  (Z)-8-(tert-Butyl-diphenyl-silanyloxy)-6-iodo-oct-5-en-2-one 在 碘代三甲硅烷 、 氟化氢吡啶 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.83h， 生成 (Z)-(S)-3,8-Dihydroxy-6-iodo-oct-5-en-2-one
  参考文献：
  名称：

  Probing the SAR of dEpoB via Chemical Synthesis:  A Total Synthesis Evaluation of C26-(1,3-dioxolanyl)-12,13-desoxyepothilone B

  摘要：

  A practical total synthesis of 26-(1,3-dioxolanyl)-12,13-desoxyepothilone B (26-dioxolanyl dEpoB) was accomplished in a highly convergent manner. A novel sequence was developed to produce the vinyl iodide segment 17 in high enantiomeric excess, which was used in a key B-alkyl Suzuki merger. Subsequently, a Yamaguchi macrocyclization formed the core lactone, while a selective oxidation and a late stage Noyori acetalization incorporated the dioxolane functionality. Sufficient amounts of synthetic 26-dioxolane dEpoB were produced using this sequence for an in vivo analysis in mice containing xenograft CCRF-CEM tumors.

  DOI：

  10.1021/jo020180q