(5E,7E,9E)-(2S,3S)-2-Hydroxy-3,5,9-trimethyl-10-(2-methyl-oxazol-4-yl)-deca-5,7,9-trien-4-one | 139631-06-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5E,7E,9E)-(2S,3S)-2-Hydroxy-3,5,9-trimethyl-10-(2-methyl-oxazol-4-yl)-deca-5,7,9-trien-4-one
• CAS: 139631-06-4
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: FXUYEUYKMHFWNR-PNLBTRILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.33
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5E,7E,9E)-(2S,3S)-2-Hydroxy-3,5,9-trimethyl-10-(2-methyl-oxazol-4-yl)-deca-5,7,9-trien-4-one 在 4-甲基苯磺酸吡啶 、 tetramethylammonium triacetoxyborohydride 作用下， 以 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 生成 2-Methyl-4-[(1E,3E,5E)-2-methyl-6-((4R,5S,6S)-2,2,5,6-tetramethyl-[1,3]dioxan-4-yl)-hepta-1,3,5-trienyl]-oxazole
  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：

  (1'E,3'E)-4-(5'-Hydroxy-2'-methyl-1',3'-pentadienyl)-2-methyloxazole 在 manganese(IV) oxide 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (5E,7E,9E)-(2S,3S)-2-Hydroxy-3,5,9-trimethyl-10-(2-methyl-oxazol-4-yl)-deca-5,7,9-trien-4-one
  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