Hexanedioic acid mono-((3Z,6Z)-heptadeca-3,6-dienyl) ester | 130727-91-2

• 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: Hexanedioic acid mono-((3Z,6Z)-heptadeca-3,6-dienyl) ester
• 英文别名: 6-[(3Z,6Z)-heptadeca-3,6-dienoxy]-6-oxohexanoic acid
• CAS: 130727-91-2
• 化学式: C₂₃H₄₀O₄
• 分子量: 380.568
• InChiKey: ICUTUXKWYSJIHS-HDXUUTQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  27
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Hexanedioic acid mono-((3Z,6Z)-heptadeca-3,6-dienyl) ester 生成 (4E,6Z)-Hexadeca-4,6-diene-1,3-diol
  参考文献：
  名称：

  DATCHEVA, VIOLETA K.;KISS, KATALIN;SOLOMON, LISA;KYLER, KEITH S., J. AMER. CHEM. SOC., 113,(1991) N, C. 270-274

  摘要：

  DOI：
• 作为产物：
  描述：

  十一醛 在 吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 Hexanedioic acid mono-((3Z,6Z)-heptadeca-3,6-dienyl) ester
  参考文献：
  名称：

  Asymmetric hydroxylation with lipoxygenase: the role of group hydrophobicity on regioselectivity

  摘要：

  Changes in the regioselectivity for the lipoxygenase 1 catalyzed oxidation of the unnatural substrates 5a-f [(Z,-Z)-HOOC(CH2)4C( = O)O(CH = CHCH2CH = CHR; R, a-f = n-C5H11-n-C10H21[ to afford regioisomeric diols 3 ](Z,E)-HOCH2CH2CH = CHCH = CHCH(OH)R[ and 4 ](E,Z)-HOCH2CH2CH(OH)CH = CH = CHR] as a function of the hydrophobicity of the distal R group were investigated. The results demonstrate that the ratio of products 3/4 decreases steadily as the hydrophobicity of the distal group is increased incrementally from n-C5H11 to n-C10H21. Conversley, changes in the proximal group hydrophobicity by varying the prosthetic modifier for substrates 6a-e {(Z,Z)-HOOC(CH2)xC-(= O)O(CH2)2CH = CHCH2H = CHC8H17; X, a-e = 2-6) gave opposite changes in the regiospecificity of oxidation. For example, increasing the hydrophobicity of the proximal group from X = 4 = 6 led to an increase in the regioselective formation of diol 3. Decreasing the value of X led to preferential formation of diol 4. Hence, the regiochemical outcome of the enzyme-catalyzed reaction appears to be influenced by the hydrophobic differential between the proximal and distal groups. The data suggests that optimization of the regioselectivity for new substrates can be achieved by careful selection of modifier groups used in the design of substrate structure.

  DOI：

  10.1021/ja00001a039

文献信息

• HUFFMAN, JOHN W.;JOYNER, H. HOWARD;LEE, MELISSA D.;JORDAN, ROBERT D.;PENN+, J. ORG. CHEM., 56,(1991) N, C. 2081-2086
  作者：HUFFMAN, JOHN W.、JOYNER, H. HOWARD、LEE, MELISSA D.、JORDAN, ROBERT D.、PENN+

  DOI：——

  日期：——
• DATCHEVA, VIOLETA K.;KISS, KATALIN;SOLOMON, LISA;KYLER, KEITH S., J. AMER. CHEM. SOC., 113,(1991) N, C. 270-274
  作者：DATCHEVA, VIOLETA K.、KISS, KATALIN、SOLOMON, LISA、KYLER, KEITH S.

  DOI：——

  日期：——
• Asymmetric hydroxylation with lipoxygenase: the role of group hydrophobicity on regioselectivity
  作者：Violeta K. Datcheva、Katalin Kiss、Lisa Solomon、Keith S. Kyler

  DOI：10.1021/ja00001a039

  日期：1991.1

  Changes in the regioselectivity for the lipoxygenase 1 catalyzed oxidation of the unnatural substrates 5a-f [(Z,-Z)-HOOC(CH2)4C( = O)O(CH = CHCH2CH = CHR; R, a-f = n-C5H11-n-C10H21[ to afford regioisomeric diols 3 ](Z,E)-HOCH2CH2CH = CHCH = CHCH(OH)R[ and 4 ](E,Z)-HOCH2CH2CH(OH)CH = CH = CHR] as a function of the hydrophobicity of the distal R group were investigated. The results demonstrate that the ratio of products 3/4 decreases steadily as the hydrophobicity of the distal group is increased incrementally from n-C5H11 to n-C10H21. Conversley, changes in the proximal group hydrophobicity by varying the prosthetic modifier for substrates 6a-e (Z,Z)-HOOC(CH2)xC-(= O)O(CH2)2CH = CHCH2H = CHC8H17; X, a-e = 2-6) gave opposite changes in the regiospecificity of oxidation. For example, increasing the hydrophobicity of the proximal group from X = 4 = 6 led to an increase in the regioselective formation of diol 3. Decreasing the value of X led to preferential formation of diol 4. Hence, the regiochemical outcome of the enzyme-catalyzed reaction appears to be influenced by the hydrophobic differential between the proximal and distal groups. The data suggests that optimization of the regioselectivity for new substrates can be achieved by careful selection of modifier groups used in the design of substrate structure.