4-((E)-(S)-6-Iodo-3-methoxymethoxy-2-methyl-hex-1-en-5-ynyl)-2-methyl-thiazole | 186692-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-((E)-(S)-6-Iodo-3-methoxymethoxy-2-methyl-hex-1-en-5-ynyl)-2-methyl-thiazole
• CAS: 186692-80-8
• 化学式: C₁₃H₁₆INO₂S
• 分子量: 377.246
• InChiKey: WLIYHXYLYVNRLS-RSPDNQDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  31.35
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-((E)-(S)-6-Iodo-3-methoxymethoxy-2-methyl-hex-1-en-5-ynyl)-2-methyl-thiazole 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 bis(cyclohexanyl)borane 、 potassium carbonate 、 溶剂黄146 、 苯硫酚 、 三乙胺 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 9.25h， 生成
  参考文献：
  名称：

  Total Syntheses of Epothilones A and B

  摘要：

  Convergent, stereocontrolled total syntheses of the microtubule-stabilizing macrolides epothilones A (2) and B (3) have been achieved. Four distinct ring-forming strategies were pursued (see Scheme 1). Of these four, three were reduced to practice. In one approach, the action of a base on a substance possessing an acetate ester and a nonenolizable aldehyde brought about a remarkably effective macroaldolization see (89 --> 90 + 91; 99 --> 100 + 101), simultaneously creating the C2-C3 bond and the hydroxyl-bearing stereocenter at C-3. Alternatively, the 16-membered macrolide of the epothilones could be fashioned through a C12-C13 ring-closing olefin metathesis (e.g. see 111 --> 90 + 117; 122 --> 105 + 123) and through macrolactonization of the appropriate hydroxy acid (e.g. see 88 --> 93). The application of a stereospecific B-alkyl Suzuki coupling strategy permitted the establishment of a cis C12-C13 olefin, thus setting the stage for an eventual site-and diastereoselective epoxidation reaction (see 96 --> 2; 106 --> 3). The development of a novel cyclopropane solvolysis strategy for incorporating the geminal methyl groups of the epothilones (see 39 --> 40 --> 41), and the use of Lewis acid catalyzed diene-aldehyde cyclocondensation (LACDAC) (see 35 + 36 --> 37) and asymmetric allylation (see 10 --> 76) methodology are also noteworthy.

  DOI：

  10.1021/ja971946k
• 作为产物：
  描述：

  4-((E)-(S)-3-Methoxymethoxy-2-methyl-6-trimethylsilanyl-hex-1-en-5-ynyl)-2-methyl-thiazole 在 N-碘代丁二酰亚胺 、 silver nitrate 作用下， 以 丙酮 为溶剂， 以64%的产率得到4-((E)-(S)-6-Iodo-3-methoxymethoxy-2-methyl-hex-1-en-5-ynyl)-2-methyl-thiazole
  参考文献：
  名称：

  Total Syntheses of Epothilones A and B

  摘要：

  Convergent, stereocontrolled total syntheses of the microtubule-stabilizing macrolides epothilones A (2) and B (3) have been achieved. Four distinct ring-forming strategies were pursued (see Scheme 1). Of these four, three were reduced to practice. In one approach, the action of a base on a substance possessing an acetate ester and a nonenolizable aldehyde brought about a remarkably effective macroaldolization see (89 --> 90 + 91; 99 --> 100 + 101), simultaneously creating the C2-C3 bond and the hydroxyl-bearing stereocenter at C-3. Alternatively, the 16-membered macrolide of the epothilones could be fashioned through a C12-C13 ring-closing olefin metathesis (e.g. see 111 --> 90 + 117; 122 --> 105 + 123) and through macrolactonization of the appropriate hydroxy acid (e.g. see 88 --> 93). The application of a stereospecific B-alkyl Suzuki coupling strategy permitted the establishment of a cis C12-C13 olefin, thus setting the stage for an eventual site-and diastereoselective epoxidation reaction (see 96 --> 2; 106 --> 3). The development of a novel cyclopropane solvolysis strategy for incorporating the geminal methyl groups of the epothilones (see 39 --> 40 --> 41), and the use of Lewis acid catalyzed diene-aldehyde cyclocondensation (LACDAC) (see 35 + 36 --> 37) and asymmetric allylation (see 10 --> 76) methodology are also noteworthy.

  DOI：

  10.1021/ja971946k

文献信息

• Balog, Aaron; Meng, Dongfang; Kamenecka, Ted, Angewandte Chemie, 1996, vol. 108, # 23/24, p. 2976 - 2978
  作者：Balog, Aaron、Meng, Dongfang、Kamenecka, Ted、Bertinato, Peter、Su, Dai-Shi、et al.

  DOI：——

  日期：——