(S)-2-hydroxy-4-pentenoic acid | 38996-05-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-hydroxy-4-pentenoic acid
• 英文别名: (S)-3-hydroxy-4-pentenoic acid；3(S)-hydroxy-4-pentenoic acid；[S,(+)]-3-Hydroxy-4-pentenoic acid；(3S)-3-hydroxypent-4-enoic acid
• CAS: 38996-05-3
• 化学式: C₅H₈O₃
• 分子量: 116.117
• InChiKey: AINRQBNLOBQURT-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxy-4-pentenoic acid 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (S)-1,3-dihydroxy-4-pentene
  参考文献：
  名称：

  Homochiral 4-hydroxy-5-hexenoic acids and their derivatives and homologues from carbohydrates

  摘要：

  Efficient routes to chiral 4-hydroxy-5-hexenoic acids and lactones from D-gluconic acid-delta -lactone and L-mannonic acid-gamma -lactone are described. In this approach, the starting lactones are converted to 2,6-dibromo compounds that readily undergo zinc mediated elimination to generate the terminal alkene group in concert with 2-deoxygenation. The integrity of the remaining stereocenters is preserved during the reaction. The related important pharmaceutical intermediates (S)-3-hydroxy-4-pentenoic acid and (S)-1.3-dihydroxy-4-pentene were also prepared from 2-deoxyribose via the corresponding aldonolactone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00053-2
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 氢溴酸 、 溴 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 19.0h， 生成 (S)-2-hydroxy-4-pentenoic acid
  参考文献：
  名称：

  Homochiral 4-hydroxy-5-hexenoic acids and their derivatives and homologues from carbohydrates

  摘要：

  Efficient routes to chiral 4-hydroxy-5-hexenoic acids and lactones from D-gluconic acid-delta -lactone and L-mannonic acid-gamma -lactone are described. In this approach, the starting lactones are converted to 2,6-dibromo compounds that readily undergo zinc mediated elimination to generate the terminal alkene group in concert with 2-deoxygenation. The integrity of the remaining stereocenters is preserved during the reaction. The related important pharmaceutical intermediates (S)-3-hydroxy-4-pentenoic acid and (S)-1.3-dihydroxy-4-pentene were also prepared from 2-deoxyribose via the corresponding aldonolactone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00053-2

文献信息

• Substrate Evaluation of<i>Rhodococcus erythropolis</i>SET1, a Nitrile Hydrolysing Bacterium, Demonstrating Dual Activity Strongly Dependent on Nitrile Sub-Structure
  作者：Tracey M. Coady、Lee V. Coffey、Catherine O'Reilly、Claire M. Lennon

  DOI：10.1002/ejoc.201403201

  日期：2015.2

  Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position

  红球菌 SET1 是一种新型腈水解细菌分离株，已使用 34 种腈、33 种手性和 1 种前手性进行了评估。这些底物主要由 β-羟基腈组成，在 β 位具有不同的烷基和芳基，并且在几种化合物中含有与腈不同的 α 取代基。在 α 位没有取代的 β-羟基腈的情况下，由于分离物的腈水解酶活性，酸是获得的主要产物，以及生物转化后回收的腈。出乎意料的是，当 β-羟基腈在该位置具有乙烯基时，发现酰胺是主要的水解产物。为了进一步探索这种行为，评估了在 α 位置包含吸电子基团的其他相关底物，在 SET1 存在下的生物转化过程中也观察到了酰胺。因此，这种新的分离物也证明了对似乎是底物依赖性的腈类的 NHase 活性。
• Radical routes to indolizidines. Synthesis of (-)-slaframine
  作者：Spencer Knapp、Frank S. Gibson

  DOI：10.1021/jo00044a011

  日期：1992.8

  The synthesis of (-)-slaframine (5) was executed in 11 steps and 25% overall yield from resolved 3(S)-hydroxy-4-pentenamide (22). Two cyclization reactions were used to form the indolizidine skeleton and also to provide the necessary stereocontrol at C-8a and C-6 of the natural product. "Iodolactamization" of 22 gave selectively the cis-pyrrolidinone 21. Later in the synthesis, a silane-mediated radical cyclization of the phenylseleno lactam 33 gave selectively the 6-alpha-hydroxyindolizidinone 35a, an event predictable from model studies-such as 14c --> 15c. Replacement of hydroxy with azido and reduction of the lactam carbonyl gave "slaframine azide", 38, a stable and easily convertible immediate precursor to 5.
• Graef, Silke; Braun, Manfred, Liebigs Annalen der Chemie, 1993, # 10, p. 1091 - 1098
  作者：Graef, Silke、Braun, Manfred

  DOI：——

  日期：——
• Homochiral 4-hydroxy-5-hexenoic acids and their derivatives and homologues from carbohydrates
  作者：Jie Song、Rawle I. Hollingsworth

  DOI：10.1016/s0957-4166(01)00053-2

  日期：2001.3

  Efficient routes to chiral 4-hydroxy-5-hexenoic acids and lactones from D-gluconic acid-delta -lactone and L-mannonic acid-gamma -lactone are described. In this approach, the starting lactones are converted to 2,6-dibromo compounds that readily undergo zinc mediated elimination to generate the terminal alkene group in concert with 2-deoxygenation. The integrity of the remaining stereocenters is preserved during the reaction. The related important pharmaceutical intermediates (S)-3-hydroxy-4-pentenoic acid and (S)-1.3-dihydroxy-4-pentene were also prepared from 2-deoxyribose via the corresponding aldonolactone. (C) 2001 Elsevier Science Ltd. All rights reserved.