2-羟基戊醛 | 87503-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-羟基戊醛
• 英文名称: 2-hydroxylpentanal
• 英文别名: 2-hydroxy-valeraldehyde；2-Hydroxy-pentanal-(1)；2-Hydroxy-valeraldehyd；2-Hydroxypentanal
• CAS: 87503-46-6
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: SUTLBTHMXYSMSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-羟基戊醛 在 copper acetylacetonate 、 氧气 、 sodium hydroxide 、 1,3-bis(2,4,6-trimethylphenyl)imidazolidine 作用下， 以 水 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以99%的产率得到2-羟基戊酸
  参考文献：
  名称：

  催化费林反应：水中铜催化的醛的高效好氧氧化

  摘要：

  报道了均相铜催化的醛的好氧氧化的第一个例子。该方法利用大气中的氧气作为唯一的氧化剂，在极其温和的水性条件下进行，并涵盖了各种功能化醛类。色谱法通常对于产品纯化不是必需的。

  DOI：

  10.1002/anie.201604847
• 作为产物：
  描述：

  1,1-dimethoxy-pentan-2-ol 在 Dowex AG-50W-X₈ (H(+) form) 水 作用下， 反应 36.0h， 生成 2-羟基戊醛
  参考文献：
  名称：

  Substrate specificity and carbohydrate synthesis using transketolase

  摘要：

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.

  DOI：

  10.1021/jo00048a023

文献信息

• Levene; Walti, Journal of Biological Chemistry, 1931, vol. 94, p. 365
  作者：Levene、Walti

  DOI：——

  日期：——
• Catalytic Fehling's Reaction: An Efficient Aerobic Oxidation of Aldehyde Catalyzed by Copper in Water
  作者：Mingxin Liu、Chao-Jun Li

  DOI：10.1002/anie.201604847

  日期：2016.8.26

  The first example of homogeneous copper‐catalyzed aerobic oxidation of aldehydes is reported. This method utilizes atmospheric oxygen as the sole oxidant, proceeds under extremely mild aqueous conditions, and covers a wide range of various functionalized aldehydes. Chromatography is generally not necessary for product purification.

  报道了均相铜催化的醛的好氧氧化的第一个例子。该方法利用大气中的氧气作为唯一的氧化剂，在极其温和的水性条件下进行，并涵盖了各种功能化醛类。色谱法通常对于产品纯化不是必需的。
• Substrate specificity and carbohydrate synthesis using transketolase
  作者：Yoshihiro Kobori、David C. Myles、George M. Whitesides

  DOI：10.1021/jo00048a023

  日期：1992.10

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.