(Z,Z)-3,6-dodecadienyl 1-monoadipate | 124099-36-1

• 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: (Z,Z)-3,6-dodecadienyl 1-monoadipate
• 英文别名: 6-[(3Z,6Z)-dodeca-3,6-dienoxy]-6-oxohexanoic acid
• CAS: 124099-36-1
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: IJOWOOJWNFSENC-HZJYTTRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (Z,Z)-3,6-dodecadienyl 1-monoadipate 生成 (3Z,5E,7S)-3,5-dodecadiene-1,7-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：

  Triphenyl-[(Z)-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-phosphonium; iodide 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 (Z,Z)-3,6-dodecadienyl 1-monoadipate
  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

• Soybean lipoxygenase: Substrate structure and product selectivity
  作者：Gerhard Scheller、Elke Jaeger、Bettina Hoffmann、Marko Schmitt、Peter Schreier

  DOI：10.1021/jf00055a005

  日期：1995.7

  To study the influence of structural properties of the substrate on the selectivity of the dioxygenation catalyzed by soybean lipoxygenase (LOX), a number of synthesized (Z,Z)-3,6-dienyl 1-adipates with various distal residues were used and the kinetic parameters, the regioselectivity, and the enantioselectivity of product formation determined. Product analysis comprised the reduction of hydroperoxides, derivatization to their methyl esters, purification by silica gel chromatography, and subsequent HPLC separation of (Z,E)-1,3-hydroxydiene methyl esters using both achiral and chiral phases. Enantioseparations were performed by HPLC on chiral phases employing both underivatized products and naphthoylate derivatives. The calculation of the hydrophobicity difference between the distal and the proximal residues of the substrate was confirmed to be a quantitative parameter to predict the positional specificity of the enzymic catalysis. enantiomeric excess was observed only for 7-oxygenated products; 3-oxygenated products were found to be racemic.
• PLAMONDON, LOUIS;WUEST, JAMES D., J. ORG. CHEM., 56,(1991) N, C. 2076-2081
  作者：PLAMONDON, LOUIS、WUEST, JAMES D.

  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：——
• Enzymic asymmetric hydroxylation of pentadienols using soybean lipoxygenase
  作者：P. Zhang、Keith S. Kyler

  DOI：10.1021/ja00208a024

  日期：1989.12
• 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.