(1'E,3'E)-4-(4'-(Methoxycarbonyl)-2'-methyl-1',3'-butadienyl)-2-methyloxazole | 139630-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1'E,3'E)-4-(4'-(Methoxycarbonyl)-2'-methyl-1',3'-butadienyl)-2-methyloxazole
• 英文别名: 2,4-Pentadienoic acid, 4-methyl-5-(2-methyl-4-oxazolyl)-, methyl ester, (E,E)-；methyl (2E,4E)-4-methyl-5-(2-methyl-1,3-oxazol-4-yl)penta-2,4-dienoate
• CAS: 139630-92-5
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: JUDQPVBQXAQLOR-DVBIZMGNSA-N

物化性质

• 沸点：
  324.7±25.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1'E,3'E)-4-(4'-(Methoxycarbonyl)-2'-methyl-1',3'-butadienyl)-2-methyloxazole 在 manganese(IV) oxide 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 40.5h， 生成 Methyl (1R(1'E,3'E,5'E),2S,3S,5S)-3-O-(tert-butyldiphenylsilyl)-1-(1',5'-dimethyl-6'-(2-methyloxazol-4-yl)-1',3',5'-hexatrienyl)-2-methyl-2,4-dideoxymannopyranoside
  参考文献：
  名称：

  Synthesis of the lower subunit of rhizoxin

  摘要：

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.

  DOI：

  10.1021/jo00034a010
• 作为产物：
  描述：

  2-甲基-4-恶唑甲酸乙酯 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 苯 为溶剂， 反应 47.71h， 生成 (1'E,3'E)-4-(4'-(Methoxycarbonyl)-2'-methyl-1',3'-butadienyl)-2-methyloxazole
  参考文献：
  名称：

  Synthesis of the lower subunit of rhizoxin

  摘要：

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.

  DOI：

  10.1021/jo00034a010

文献信息

• Synthesis of the lower subunit of rhizoxin
  作者：Dale L. Boger、Timothy T. Curran

  DOI：10.1021/jo00034a010

  日期：1992.4

  Full details of a study leading to a synthesis of the optically active C13-C26 lower subunit of rhizoxin including the side-chain chromophore characteristic of the full class of antimitotic agents are described. A key element of the synthesis is the stereoselective introduction of the C18-C19 trisubstituted olefin through use of a Wadsworth-Horner-Emmons condensation of 3 with beta-keto phosphonate 38 bearing resident functionality suitable for the diastereoselective introduction of C15-C17 employing a hydroxyl-directed reduction of the resultant beta-hydroxy ketone.