(2S)-2-ethyl-2,3-epoxypropanol | 131703-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S)-2-ethyl-2,3-epoxypropanol
• 英文别名: (s)-2-Ethylglycidol；[(2S)-2-ethyloxiran-2-yl]methanol
• CAS: 131703-68-9
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: NXPXQOGPODGJKY-YFKPBYRVSA-N

物化性质

• 沸点：
  160.4±8.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-ethyl-2,3-epoxypropanol 在 copper(l) iodide 、 对甲苯磺酸 、 臭氧 、 三苯基膦 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 54.25h， 生成 (4R)-4-ethyl-4,5-dihydroxypentanal acetonide
  参考文献：
  名称：

  Enantioselective syntheses of vinblastine, leurosidine, vincovaline and 20'-epi-vincovaline

  摘要：

  The binary indole-indoline alkaloids vinblastine (1), leurosidine (13), 20'-epi-vincovaline (14a), and vincovaline (14b) were obtained by coupling of vindoline (3) to the tetracyclic intermediates 7a, 7b or 22a, 22b, followed by reduction and cyclization steps (60% overall yield for these reactions). The intermediates were obtained by enantioselective establishment of C20' through a first-step Sharpless oxidation (10a,b) and followed by a subsequent diastereomeric separation (20a,b or 21a,b). Alternatively, enantioselective control of the key secodine-type cyclization in the reaction sequence provided the tetracyclic intermediates 54 and 60 for coupling to vindoline. Selective generation of the natural (1, 13, 14a,b) or unnatural (30, 34, 35a,b) atropisomeric forms of the alkaloids was achieved through alternative closures of ring D'. The natural products were also obtained from the higher energy atropisomers by conformational inversion on heating. For the vinblastine synthesis, the overall yield was 22%.

  DOI：

  10.1021/jo00002a008
• 作为产物：
  描述：

  2-Methylene-1-butanol 生成 (2S)-2-ethyl-2,3-epoxypropanol
  参考文献：
  名称：

  KUEHNE, MARTIN E.;MATSON, PATRICIA A.;BORNMANN, WILLIAM G., J. ORG. CHEM., 56,(1991) N, C. 513-528

  摘要：

  DOI：

文献信息

• Stereospecific synthesis of the top-half precursor to the antitumor agent vinblastine and a simple bisindole analogue.
  作者：Philip Magnus、José Mendoza

  DOI：10.1016/s0040-4039(00)91570-3

  日期：1992.2

  The stereospecific synthesis of a precursor to the top-half of vinblastine is described. Its non-oxidative coupling to m-methoxy-N,N-dimethylaniline provides access to the vinblastine analogue 18.

  描述了长春碱前半部分前体的立体定向合成。其非氧化偶合到米-甲氧基- N，N-二甲基苯胺提供对长春碱类似物18。
• Synthesis of Plakortone B and Analogs
  作者：M. F. Semmelhack、Richard J. Hooley、Christina M. Kraml

  DOI：10.1021/ol0618656

  日期：2006.11.9

  Use of a palladium-mediated alkoxycarbonylation/lactonization process provides a variable route to analogs of the plakortones. Four different analogs, including natural plakortone B, have been synthesized via this route.
• Magnus, Philip; Mendoza, José S.; Stamford, Andrew, Journal of the American Chemical Society, 1992, vol. 114, # 26, p. 10232 - 10245
  作者：Magnus, Philip、Mendoza, José S.、Stamford, Andrew、Ladlow, Mark、Willis, Paul

  DOI：——

  日期：——
• KUEHNE, MARTIN E.;MATSON, PATRICIA A.;BORNMANN, WILLIAM G., J. ORG. CHEM., 56,(1991) N, C. 513-528
  作者：KUEHNE, MARTIN E.、MATSON, PATRICIA A.、BORNMANN, WILLIAM G.

  DOI：——

  日期：——
• Enantioselective syntheses of vinblastine, leurosidine, vincovaline and 20'-epi-vincovaline
  作者：Martin E. Kuehne、Patricia A. Matson、William G. Bornmann

  DOI：10.1021/jo00002a008

  日期：1991.1

  The binary indole-indoline alkaloids vinblastine (1), leurosidine (13), 20'-epi-vincovaline (14a), and vincovaline (14b) were obtained by coupling of vindoline (3) to the tetracyclic intermediates 7a, 7b or 22a, 22b, followed by reduction and cyclization steps (60% overall yield for these reactions). The intermediates were obtained by enantioselective establishment of C20' through a first-step Sharpless oxidation (10a,b) and followed by a subsequent diastereomeric separation (20a,b or 21a,b). Alternatively, enantioselective control of the key secodine-type cyclization in the reaction sequence provided the tetracyclic intermediates 54 and 60 for coupling to vindoline. Selective generation of the natural (1, 13, 14a,b) or unnatural (30, 34, 35a,b) atropisomeric forms of the alkaloids was achieved through alternative closures of ring D'. The natural products were also obtained from the higher energy atropisomers by conformational inversion on heating. For the vinblastine synthesis, the overall yield was 22%.