7,8-O-isopropylidene-7(R),8-dihydroxyoctanoic acid | 146943-57-9

• 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: 7,8-O-isopropylidene-7(R),8-dihydroxyoctanoic acid
• 英文别名: 6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]hexanoic acid
• CAS: 146943-57-9
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: BBJIQQQBNCXREV-VIFPVBQESA-N

物化性质

• 沸点：
  327.0±17.0 °C(predicted)
• 密度：
  1.042±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 7,8-O-isopropylidene-7(R),8-dihydroxyoctanoic acid 在 Dowex 50W-X₈ 、 氢气 作用下， 反应 24.0h， 以85%的产率得到methyl 7(S),8-dihydroxyoctanoate
  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：

  4-羧丁基三苯基溴化膦 在 platinum on activated charcoal 氢气 、 双(三甲基硅烷基)氨基钾 作用下， 以 正己烷 为溶剂， 反应 2.75h， 生成 7,8-O-isopropylidene-7(R),8-dihydroxyoctanoic acid
  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

文献信息

• 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.