(3Z,6Z)-pentadeca-3,6-dien-1-ol | 130727-72-9

• 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: (3Z,6Z)-pentadeca-3,6-dien-1-ol
• CAS: 130727-72-9
• 化学式: C₁₅H₂₈O
• 分子量: 224.387
• InChiKey: KRKGYOLWKFJJJV-UTJQPWESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3Z,6Z)-pentadeca-3,6-dien-1-ol 在 吡啶 、 borate buffer 、 arachidonate 8-lipoxygenase 、 硫酸 、 氧气 、 对甲苯磺酰氯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (3Z,5E)-(S)-Pentadeca-3,5-diene-1,7-diol
  参考文献：
  名称：

  在大豆脂氧合酶对烯烃的酶促过氧化反应中，新的最小底物结构要求。

  摘要：

  脂肪酸类似物中的羧基或带电荷的头基对于大豆脂氧合酶-1催化的氧化反应中的结合和催化作用不是必不可少的结构要求。

  DOI：

  10.1016/s0960-894x(98)00680-5
• 作为产物：
  描述：

  壬醛 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (3Z,6Z)-pentadeca-3,6-dien-1-ol
  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

• Synthesis of methyl (1R,2S)-2-[(1′Z,4′Z,7′Z)-hexadeca-1′,4′,7′-trienyl]cyclopropanecarboxylate: a potential inhibitor of the enzyme 5-lipoxygenase
  作者：Paul I. Butler、Trafford Clarke、Colin Dell、John Mann

  DOI：10.1039/p19940001503

  日期：——

  We describe the synthesis of a novel cyclopropyl analogue of arachidonic acid via a convergent synthesis that employed methyl (1R,2S)-2-formylcyclopropanecarboxylate in conjunction with the ylide from (3Z,6Z)-pentadeca-3,6-dienyl(triphenyl)phosphonium iodide. This compound was designed to inhibit the enzyme 5-lipoxygenase after reaction to form a putative α-cyclopropylmethylene radical.

  我们描述了一种新的花生四烯酸环丙基类似物的合成，该合成通过使用（1 R，2 S）-2-甲酰基环丙烷甲酸甲酯与（3 Z，6 Z）-pentadeca-3,6-的叶立德一起使用的会聚合成来合成。二烯基（三苯基）碘化.。该化合物被设计成在反应形成抑制的α-环丙基亚甲基后抑制酶5-脂氧合酶。
• 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.
• New minimal substrate structural requirements in the enzymatic peroxidation of alkenes with soybean lipoxygenase
  作者：Mark J. Novak

  DOI：10.1016/s0960-894x(98)00680-5

  日期：1999.1

  A carboxylic or a charged head group in fatty acid analogs is not an essential structural requirement for binding and catalysis in soybean lipoxygenase-1 catalyzed oxidations.

  脂肪酸类似物中的羧基或带电荷的头基对于大豆脂氧合酶-1催化的氧化反应中的结合和催化作用不是必不可少的结构要求。