3-hydroxyphenethyl 2-((1S,3S,4R,E)-2-ethylidene-3,4-dihydroxycyclopentyl)acetate | 956964-09-3

• 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: 3-hydroxyphenethyl 2-((1S,3S,4R,E)-2-ethylidene-3,4-dihydroxycyclopentyl)acetate
• CAS: 956964-09-3
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: ZLBUNWSZPKWUIB-PUJIVUIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-hydroxyphenethyl 2-((1S,3S,4R,E)-2-ethylidene-3,4-dihydroxycyclopentyl)acetate 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (3S,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid 2-(3-hydroxyphenyl)ethyl ester
  参考文献：
  名称：

  Syntheses of (−)-Oleocanthal, a Natural NSAID Found in Extra Virgin Olive Oil, the (−)-Deacetoxy-Oleuropein Aglycone, and Related Analogues

  摘要：

  Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.

  DOI：

  10.1021/jo071146k
• 作为产物：
  描述：

  (-)-(3Ar,6ar)-四氢-2,2-二甲基-4H-环戊并-1,3-二氧代-4-酮 在 盐酸 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 lithium hydroxide 、 cerium(III) chloride 、 氢氟酸 、 四丁基氟化铵 、 Dimethylzinc 、 双(三甲基硅烷基)氨基钾 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 3-hydroxyphenethyl 2-((1S,3S,4R,E)-2-ethylidene-3,4-dihydroxycyclopentyl)acetate
  参考文献：
  名称：

  Syntheses of (−)-Oleocanthal, a Natural NSAID Found in Extra Virgin Olive Oil, the (−)-Deacetoxy-Oleuropein Aglycone, and Related Analogues

  摘要：

  Phenolic compounds extracted from extra virgin olive oil have attracted considerable recent attention. One of the components, (-)-oleocanthal (1), an inhibitor of the COX-1 and COX-2 enzymes, possesses similar potency as the NSAID ibuprofen. In this, a full account, we disclose the first- and now second-generation syntheses of both enantiomers of the oleocanthals, as well as the first synthesis of the closely related (-)-deacetoxy-oleuropein aglycone and a series of related analogues for structure activity studies. To demonstrate the utility of the second-generation synthesis, multigram quantities of (-)-oleocanthal were prepared in 10 steps (14% overall yield) from commercially available D-lyxose.

  DOI：

  10.1021/jo071146k