(S)-3-hydroxy-5-hexen-2-one | 252265-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-hydroxy-5-hexen-2-one
• 英文别名: (3S)-3-hydroxyhex-5-en-2-one
• CAS: 252265-28-4
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: XQUYLAGLGAHCHT-LURJTMIESA-N

物化性质

• 沸点：
  193.3±20.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-3-hydroxy-5-hexen-2-one 在 Grubbs catalyst first generation 、 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-(S)-10-[(E)-1-Methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one
  参考文献：
  名称：

  Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylation

  摘要：

  An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01659-7
• 作为产物：
  描述：

  5-已烯-2-酮 在 α-AD mix {K4[Fe(CN)6], OsO4, Na2CO3, (DHQ)2-PHAL} 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (S)-3-hydroxy-5-hexen-2-one
  参考文献：
  名称：

  Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylation

  摘要：

  An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01659-7

文献信息

• A New Route to Protected Acyloins and Their Enzymatic Resolution with Lipases
  作者：Günther Scheid、Wouter Kuit、Eelco Ruijter、Romano V. A. Orru、Erik Henke、Uwe Bornscheuer、Ludger A. Wessjohann

  DOI：10.1002/ejoc.200300338

  日期：2004.3

  synthesised by a straight-forward new method through alkylation of tert-butyl 2-acyloxyacetoacetates 3, followed by chemoselective dealkoxy-carbonylation of the tert-butyloxycarbonyl group in the presence of other ester groups. Subsequent hydrolysis of (±)-5 can be achieved with base to give racemic acyloins 6, or with lipase catalysis to afford the corresponding non-racemic acyloins (S)-6. The remaining (R)-acyloin

  一系列 16 种不同的 3-酰氧基甲基酮，酰基乙酸酯和丁酸酯 (±)-5，通过一种直接的新方法通过 2-酰氧基乙酰乙酸叔丁酯 3 的烷基化合成，然后是化学选择性脱烷氧基羰基化叔丁氧羰基在其他酯基团的存在下。(±)-5 的后续水解可以用碱实现，得到外消旋 acyloins 6，或用脂肪酶催化，得到相应的非外消旋 acyloins (S)-6。剩余的(R)-丙烯酰基酯5可以外消旋并重新进行该程序，或化学水解。使用六种测试酶中的两种酶进行动力学拆分，CAL-B 和 BCL (PS) 脂肪酶，选择性地进行 [对映异构体比 (E) 值介于 50 和 > 200 之间]，并且大多数 acyloins (S)-6 以非常高对映体过量（高达 > 99% ee)。© Wiley-VCH Verlag GmbH & Co. KGaA，德国魏因海姆 69451，2004 年。
• Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylation
  作者：Monika Quitschalle、Markus Kalesse

  DOI：10.1016/s0040-4039(99)01659-7

  日期：1999.10

  An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. All rights reserved.