4(S)-4-<(1-Methoxy-1-methylethyl)dioxy>-2(E)-nonenal | 134391-24-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4(S)-4-<(1-Methoxy-1-methylethyl)dioxy>-2(E)-nonenal
• 英文别名: 4(S)-<(1-Methoxy-1-methylethyl)dioxy>-2(E)-nonenal；4(S)-4-[(1-Methoxy-1-methylethyl)dioxy]-2(E)-nonenal；(E,4S)-4-(2-methoxypropan-2-ylperoxy)non-2-enal
• CAS: 134391-24-5
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: LBZTYFRQSWGBGF-OANVXVOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4(S)-4-<(1-Methoxy-1-methylethyl)dioxy>-2(E)-nonenal 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 (2E,4E)-(S)-6-Hydroperoxy-2-methyl-undeca-2,4-dienoic acid ethyl ester
  参考文献：
  名称：

  A new synthon for optically active diene hydroperoxides

  摘要：

  The olefination of an enzymatically derived gamma-peroxy-alpha,beta-unsaturated aldehyde (1) allows the synthesis of optically active diene hydroperoxides in high enantiomeric excess. The application of this method to the synthesis of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid methyl ester is presented.

  DOI：

  10.1021/jo00013a001
• 作为产物：
  描述：

  Methyl 13(S)-<(1-methoxy-1-methylethyl)dioxy>-9(Z),11(E)-octadecadienoate 在 臭氧 、 三苯基膦 作用下， 生成 4(S)-4-<(1-Methoxy-1-methylethyl)dioxy>-2(E)-nonenal
  参考文献：
  名称：

  A new synthon for optically active diene hydroperoxides

  摘要：

  The olefination of an enzymatically derived gamma-peroxy-alpha,beta-unsaturated aldehyde (1) allows the synthesis of optically active diene hydroperoxides in high enantiomeric excess. The application of this method to the synthesis of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid methyl ester is presented.

  DOI：

  10.1021/jo00013a001

文献信息

• A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE
  作者：Patrick Dussault、In Quen Lee

  DOI：10.1021/jo00106a037

  日期：1995.1

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.
• DUSSAULT, PATRICK;LEE, IN QUEN;KREIFELS, SCOTT, J. ORG. CHEM., 56,(1991) N3, C. 4087-4089
  作者：DUSSAULT, PATRICK、LEE, IN QUEN、KREIFELS, SCOTT

  DOI：——

  日期：——
• An organometallic approach to peroxy ketals
  作者：Patrick Dussault、Ayman Sahli、Thane Westermeyer

  DOI：10.1021/jo00072a032

  日期：1993.9

  A new method for peroxyketal synthesis is presented based upon formation of carbon-carbon bonds in the presence of a protected hydroperoxide. The 2-methoxypropyl perketal of 4(S)-hydroperoxy-2(E)-nonenal (2) undergoes reaction with a variety of metal hydrides and organometallic reagents to produce 4-peroxy 2-enols in good to excellent yields via chemoselective addition to the carbonyl carbon. Oxidation of the allylic alcohol to the 4-peroxy 2-enone is followed by deprotection to furnish a single enantiomer of a 4-hydroxyperoxy 2(E)-enone. Photochemical isomerization by the method of Snider induces spontaneous cyclization to epimeric 3-hydroxy-1,2-dioxins (hydroxy endoperoxides). Acidic methanolysis furnishes readily separable diastereomeric perketals as single enantiomers.
• A new synthon for optically active diene hydroperoxides
  作者：Patrick Dussault、In Quen Lee、Scott Kreifels

  DOI：10.1021/jo00013a001

  日期：1991.6

  The olefination of an enzymatically derived gamma-peroxy-alpha,beta-unsaturated aldehyde (1) allows the synthesis of optically active diene hydroperoxides in high enantiomeric excess. The application of this method to the synthesis of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid methyl ester is presented.