2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-2,3-dihydropyran-4-one | 184246-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-2,3-dihydropyran-4-one
• CAS: 184246-39-7
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: WYMZRZIVEIDAPW-VMPITWQZSA-N

物化性质

• 沸点：
  363.1±21.0 °C(predicted)
• 密度：
  1.244±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-2,3-dihydropyran-4-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 Lipase-30 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 7.0h， 生成 [(2S,4S)-2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-3,4-dihydro-2H-pyran-4-yl] acetate
  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：

  (2E)-2-甲基-3-(2-甲基-1,3-噻唑-4-基)丙烯醛 在 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-2,3-dihydropyran-4-one
  参考文献：
  名称：

  合成埃博霉素A的研究：使用氢吡喃模板管理无环立体化学关系。

  摘要：

  DOI：

  10.1021/jo961673w

文献信息

• Total Syntheses of Epothilones A and B
  作者：Dongfang Meng、Peter Bertinato、Aaron Balog、Dai-Shi Su、Ted Kamenecka、Erik J. Sorensen、Samuel J. Danishefsky

  DOI：10.1021/ja971946k

  日期：1997.10.1

  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.
• Studies toward a Synthesis of Epothilone A:  Use of Hydropyran Templates for the Management of Acyclic Stereochemical Relationships
  作者：Dongfang Meng、Erik J. Sorensen、Peter Bertinato、Samuel J. Danishefsky

  DOI：10.1021/jo961673w

  日期：1996.11.15