9-Hydroxy-9-phenyl-nonanoic acid | 103187-35-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 9-Hydroxy-9-phenyl-nonanoic acid
• CAS: 103187-35-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: QPHBTNSBGULLIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  18.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  9-Hydroxy-9-phenyl-nonanoic acid 在 三氟化硼乙醚 、 三氯化铁 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 9-Phenyl-9-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)nonanoic acid
  参考文献：
  名称：

  Quinones. 4. Novel eicosanoid antagonists: synthesis and pharmacological evaluation

  摘要：

  A new series of omega-phenyl-omega-quinonylalkanoic acids and related compounds was synthesized. The compounds were tested for their inhibitory effects on U-44069-induced contraction of the rabbit aorta. (+/- )-7-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid (4d) (AA-2414) with pA2 value of 8.28 was one of the most potent compounds. Compound 4d inhibited U-46619-induced contraction of the guinea pig lung (pA2 = 8.29) and U-44069-induced aggregation of the guinea pig platelet (IC50 = 3.5 x 10(-7) M). Compound 4d displaced the binding of [3H]U-46619 to guinea pig platelets (IC50 = 7.4 x 10(-9) M). Compound 4d also showed very potent inhibitory effects with an MED of 0.3 mg/kg (po) on U-46619-, LTD4-, PAF-, or IgG1-induced bronchoconstriction in guinea pigs. The enantiomers of 4d were prepared. The R-(+) isomer 8a was active in both in vitro and in vivo tests, but the S-(-) isomer 8b was much less active. We concluded that the antiasthmatic effects of 4d were based mainly on the TXA2 receptor antagonistic action. In addition, compound 4d showed potent inhibitory effects on PGD2-, PGF2 alpha-, and 11-epi-PGF2 alpha-induced contraction of the guinea pig tracheal strips. The diverse inhibitory effects might be expressed in terms of eicosanoid-antagonistic activity.

  DOI：

  10.1021/jm00129a030
• 作为产物：
  描述：

  在 1-羟基环己基苯基甲酮 、 水 、 sodium t-butanolate 作用下， 以 二氯甲烷 为溶剂， 以69 %的产率得到9-Hydroxy-9-phenyl-nonanoic acid
  参考文献：
  名称：

  用 1-羟基环己基苯基酮将伯醇和醛氧化成羧酸

  摘要：

  伯醇氧化成相应的羧酸是有机合成中基本且有用的反应之一。在本文中，我们报告了通过 1-羟基环己基苯基酮介导的氢化物转移反应将伯醇和醛氧化为酸的综合结果。在叔丁醇钠的强碱性条件下，室温氧化可耐受一系列官能团，包括脆弱的叔丁亚磺酰胺、胺、硫化物、烯烃和杂环，并提供良好至优异的产率。最重要的是，我们的氧化过程可以应用于在仲醇存在下将伯醇和醛化学选择性氧化为羧酸。

  DOI：

  10.1021/acs.joc.3c00096

文献信息

• Quinones. 4. Novel eicosanoid antagonists: synthesis and pharmacological evaluation
  作者：Mitsuru Shiraishi、Kaneyoshi Kato、Shinji Terao、Yasuko Ashida、Zenichi Terashita、Go Kito

  DOI：10.1021/jm00129a030

  日期：1989.9

  A new series of omega-phenyl-omega-quinonylalkanoic acids and related compounds was synthesized. The compounds were tested for their inhibitory effects on U-44069-induced contraction of the rabbit aorta. (+/- )-7-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid (4d) (AA-2414) with pA2 value of 8.28 was one of the most potent compounds. Compound 4d inhibited U-46619-induced contraction of the guinea pig lung (pA2 = 8.29) and U-44069-induced aggregation of the guinea pig platelet (IC50 = 3.5 x 10(-7) M). Compound 4d displaced the binding of [3H]U-46619 to guinea pig platelets (IC50 = 7.4 x 10(-9) M). Compound 4d also showed very potent inhibitory effects with an MED of 0.3 mg/kg (po) on U-46619-, LTD4-, PAF-, or IgG1-induced bronchoconstriction in guinea pigs. The enantiomers of 4d were prepared. The R-(+) isomer 8a was active in both in vitro and in vivo tests, but the S-(-) isomer 8b was much less active. We concluded that the antiasthmatic effects of 4d were based mainly on the TXA2 receptor antagonistic action. In addition, compound 4d showed potent inhibitory effects on PGD2-, PGF2 alpha-, and 11-epi-PGF2 alpha-induced contraction of the guinea pig tracheal strips. The diverse inhibitory effects might be expressed in terms of eicosanoid-antagonistic activity.
• Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids with 1-Hydroxycyclohexyl Phenyl Ketone
  作者：Yi Lu、Wen-Yun Tan、Yuzhen Ding、Wen Chen、Hongbin Zhang

  DOI：10.1021/acs.joc.3c00096

  日期：2023.7.7

  The oxidation of primary alcohols to the corresponding carboxylic acids is one of the fundamental and useful reactions in organic synthesis. In this paper, we report our comprehensive results toward the oxidation of primary alcohols and aldehydes to acids via hydride transfer reactions mediated by 1-hydroxycyclohexyl phenyl ketone. Under the strong basic conditions of sodium tert-butoxide, the room

  伯醇氧化成相应的羧酸是有机合成中基本且有用的反应之一。在本文中，我们报告了通过 1-羟基环己基苯基酮介导的氢化物转移反应将伯醇和醛氧化为酸的综合结果。在叔丁醇钠的强碱性条件下，室温氧化可耐受一系列官能团，包括脆弱的叔丁亚磺酰胺、胺、硫化物、烯烃和杂环，并提供良好至优异的产率。最重要的是，我们的氧化过程可以应用于在仲醇存在下将伯醇和醛化学选择性氧化为羧酸。