methyl 5-hydroxy-6-oxohexanoate dimethyl acetal | 104681-91-6

• 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: methyl 5-hydroxy-6-oxohexanoate dimethyl acetal
• 英文别名: Methyl 5-hydroxy-6,6-dimethoxyhexanoate
• CAS: 104681-91-6
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: MQPJKKCJKSUXOY-UHFFFAOYSA-N

物化性质

• 沸点：
  279.5±40.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-6-oxohexanoate dimethyl acetal 、 dihydroxyacetone phosphate disodium salt 在 sodium hydroxide 作用下， 生成 sodium 6-deoxy-6-ethylenecarboxyfructose 1-phosphate
  参考文献：
  名称：

  Diastereoselectivity (enantioselectivity) of aldol condensations catalyzed by rabbit muscle aldolase at C-2 of RCHOHCHO if R has an appropriately placed negatively charged group

  摘要：

  D-Fructose 1,6-bis(phosphate) aldolase from rabbit muscle (RAMA, E.C. 4.1.2.13) catalyzes the aldol condensation between dihydroxyacetone phosphate (DHAP) and various aldehydes; the products are ketosugars with 3(S),4(R) stereochemistry. When racemic alpha-hydroxy aldehydes are condensed with DHAP, two diastereomeric products are formed. This paper demonstrates that RAMA can kinetically resolve alpha-hydroxy aldehydes with a negative charge removed four or five atoms from the aldehydic center. Kinetic resolution of either uncharged alpha-hydroxy aldehydes, or of alpha-hydroxy aldehydes with a negative charge removed three or seven atoms from the aldehydic carbon, is generally not as successful.

  DOI：

  10.1021/jo00059a047
• 作为产物：
  描述：

  甲醇 、 6-氧代己酸甲酯 在 氢氧化钾 、 potassium iodide 作用下， 反应 1.5h， 以33%的产率得到methyl 5-hydroxy-6-oxohexanoate dimethyl acetal
  参考文献：
  名称：

  Shono, Tatsuya; Matsumura, Yoshihiro; Inoue, Kenji, Journal of the Chemical Society. Perkin transactions I, 1986, p. 73 - 78

  摘要：

  DOI：

文献信息

• SHONO, TATSUYA;MATSUMURA, YOSHIHIRO;INOUE, KENJI;IWASAKI, FUMIAKI, J. CHEM. SOC. PERKIN TRANS., 1986, N 1, 73-77
  作者：SHONO, TATSUYA、MATSUMURA, YOSHIHIRO、INOUE, KENJI、IWASAKI, FUMIAKI

  DOI：——

  日期：——
• Shono, Tatsuya; Matsumura, Yoshihiro; Inoue, Kenji, Journal of the Chemical Society. Perkin transactions I, 1986, p. 73 - 78
  作者：Shono, Tatsuya、Matsumura, Yoshihiro、Inoue, Kenji、Iwasaki, Fumiaki

  DOI：——

  日期：——
• Diastereoselectivity (enantioselectivity) of aldol condensations catalyzed by rabbit muscle aldolase at C-2 of RCHOHCHO if R has an appropriately placed negatively charged group
  作者：Watson J. Lees、George M. Whitesides

  DOI：10.1021/jo00059a047

  日期：1993.3

  D-Fructose 1,6-bis(phosphate) aldolase from rabbit muscle (RAMA, E.C. 4.1.2.13) catalyzes the aldol condensation between dihydroxyacetone phosphate (DHAP) and various aldehydes; the products are ketosugars with 3(S),4(R) stereochemistry. When racemic alpha-hydroxy aldehydes are condensed with DHAP, two diastereomeric products are formed. This paper demonstrates that RAMA can kinetically resolve alpha-hydroxy aldehydes with a negative charge removed four or five atoms from the aldehydic center. Kinetic resolution of either uncharged alpha-hydroxy aldehydes, or of alpha-hydroxy aldehydes with a negative charge removed three or seven atoms from the aldehydic carbon, is generally not as successful.