2-羟基戊酰胺 | 66461-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基戊酰胺
• 英文名称: α-hydroxyvaleramide
• 英文别名: N-propylglycolamide；2-hydroxyvaleramide；(+/-)-2-hydroxy-valeric acid amide；(+/-)-2-Hydroxy-valeriansaeure-amid；2-Hydroxypentanamide
• CAS: 66461-72-1
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: DPSHJKZKKFYEHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-羟基戊酸 、 2-羟基戊酰胺 在 盐酸 作用下， 生成 2-羟基戊酸甲酯
  参考文献：
  名称：

  一种2-羟基戊酸甲酯的合成方法

  摘要：

  一种2‑羟基戊酸甲酯的合成方法，包括步骤：1)取氰化氢和正丁醛，以碱作为催化剂至反应完毕，得到含有丁醛氢醇的反应液A；2)反应液A、甲醇加入水中，以金属氧化物作为催化剂至反应完毕，得到反应液B；3)反应液B经固液分离，分离的固相返回步骤2)循环使用，分离的液相通入酸，升温至50‑90℃，至反应完毕，得到反应液C；4)反应液C继续升温至回流状态，得到反应液D；5)反应液D经固液分离，分离的液相经精馏得到目标产物2‑羟基戊酸甲酯。本发明可有效降低酸用量并减少废水产生，并实现原料和催化剂的循环利用，适合工业化大规模生产。

  公开号：

  CN118063321A
• 作为产物：
  描述：

  2-羟基戊腈 在 nitrile hydratase from Nitriliruptor alkaliphilus 、 水 作用下， 生成 2-羟基戊酰胺
  参考文献：
  名称：

  固定化的氧化硝化酶和腈水合酶的一锅双酶级联反应合成脂肪族（S）-α-羟基羧酸酰胺

  摘要：

  Abstractmagnified imageA one‐pot bienzymatic cascade combining a hydroxynitrile lyase (Manihot esculenta, E.C. 4.1.2.10) and a nitrile hydratase (Nitriliruptor alkaliphilus, E.C. 4.2.1.84) for the synthesis of enantiopure aliphatic α‐hydroxycarboxylic amides from aldehydes is described. Both enzymes were immobilised as cross‐linked enzyme aggregates (CLEAs). Stability tests show that the nitrile hydratase CLEAs are sensitive to water‐immiscible organic solvents as well as to aldehydes and hydrogen cyanide (HCN), but are remarkably stable and show useful activity in acidic aqueous environments of pH 4–5. The cascade reactions are consequently carried out by using a portionwise feed of HCN and moderate concentrations of aldehyde in acidic aqueous buffer to suppress the uncatalysed hydrocyanation background reaction. After optimisation, this method was used to synthesise five different kinds of aliphatic α‐hydroxycarboxylic amides from the corresponding aldehydes with good yields and with enantiomeric purities comparable to those obtained for the α‐hydroxynitriles in the microaqueous hydrocyanation using hydroxynitrile lyase and an excess of HCN.

  DOI：

  10.1002/adsc.200800625

文献信息

• BIOCHEMISTRY OF THE USTILAGINALES: IV. THE CONFIGURATIONS OF SOME β–HYDROXYACIDS AND THE BIOREDUCTION OF β–KETOACIDS
  作者：R. U. Lemieux、Jacques Giguere

  DOI：10.1139/v51-076

  日期：1951.8.1

  The basis for the assignment of the above configurations is discussed. L-α-Hydroxy-n-valeramide was reduced with lithium aluminium hydride and the product was acetylated to yield L-1-acetamido-2-acetoxypentane. The enantiomorphic form of the latter compound was obtained through the Curtius degradation of D-β-hydroxy -n-caprohydrazide. The configurations assigned to the β-hydroxy-n-caprylic acids are

  β-酮-正己酸和β-酮-正-辛酸的植物化学还原产生相应的D-β-羟基酸。该观察结果与 β-酮丁酸生物还原为 L-β-羟基丁酸形成对比。讨论了分配上述配置的基础。L-α-羟基-n-戊酰胺用氢化铝锂还原，产物乙酰化得到L-1-乙酰氨基-2-乙酰氧基戊烷。后一种化合物的对映形式是通过 D-β-羟基-n-己酰肼的 Curtius 降解获得的。分配给 β-羟基-n-辛酸的构型基于同源化合物旋光度的 Levene-Marker 规则。因此，从乌司提酸衍生的β-羟基-正己酸和β-羟基-正-辛酸被证明属于L-系列。
• EREMEEV, I. V.;ZILBERMAN, E. N.;MIROSHNICHENKO, S. V., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 1982, 25, N 5, 558-562
  作者：EREMEEV, I. V.、ZILBERMAN, E. N.、MIROSHNICHENKO, S. V.

  DOI：——

  日期：——
• Synthesis of Aliphatic (S)-α-Hydroxycarboxylic Amides using a One-Pot Bienzymatic Cascade of Immobilised Oxynitrilase and Nitrile Hydratase
  作者：Sander van Pelt、Fred van Rantwijk、Roger A. Sheldon

  DOI：10.1002/adsc.200800625

  日期：2009.2

  Abstractmagnified imageA one‐pot bienzymatic cascade combining a hydroxynitrile lyase (Manihot esculenta, E.C. 4.1.2.10) and a nitrile hydratase (Nitriliruptor alkaliphilus, E.C. 4.2.1.84) for the synthesis of enantiopure aliphatic α‐hydroxycarboxylic amides from aldehydes is described. Both enzymes were immobilised as cross‐linked enzyme aggregates (CLEAs). Stability tests show that the nitrile hydratase CLEAs are sensitive to water‐immiscible organic solvents as well as to aldehydes and hydrogen cyanide (HCN), but are remarkably stable and show useful activity in acidic aqueous environments of pH 4–5. The cascade reactions are consequently carried out by using a portionwise feed of HCN and moderate concentrations of aldehyde in acidic aqueous buffer to suppress the uncatalysed hydrocyanation background reaction. After optimisation, this method was used to synthesise five different kinds of aliphatic α‐hydroxycarboxylic amides from the corresponding aldehydes with good yields and with enantiomeric purities comparable to those obtained for the α‐hydroxynitriles in the microaqueous hydrocyanation using hydroxynitrile lyase and an excess of HCN.