3-decylcatechol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-decylcatechol
• 英文别名: 3-decylbenzene-1,2-diol
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: RIJPREMBVOLUIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-decylcatechol 、 diphosphorus pentasulfide 生成 5-decyl-2-sulfanyl-2-sulfanylidene-1,3,2λ5-benzodioxaphosphole
  参考文献：
  名称：

  YAMAGUCHI, ELAINE S.;LISTON, THOMAS V.

  摘要：

  DOI：
• 作为产物：
  描述：

  3-decylveratrole 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 14.0h， 以93%的产率得到3-decylcatechol
  参考文献：
  名称：

  Nonallergenic urushiol derivatives inhibit the oxidation of unilamellar vesicles and of rat plasma induced by various radical generators

  摘要：

  Urushiols consist of an o-dihydroxybenzene (catechol) structure and an alkyl chain of 15 or 17 carbons in the 3-position of a benzene ring and are allergens found in the family Anacardiaceae. We synthesized various veratrole (1,2-dimethoxybenzene)-type and catechol-type urushiol derivatives that contained alkyl chains of various carbon atom lengths, including -H, -C1H3, -C5H11, -C10H21, -C15H31, and -C20H41, and investigated their contact hypersensitivities and antioxidative activities. 3-Decylcatechol and 3-pentadecylcatechol displayed contact hypersensitivity, but the other compounds did not induce an allergic reaction, when the ears of rats were sensitized by treatment with the compounds every day for 20 days. Catechol-type urushiol derivatives (CTUDs) exerted very high radical-scavenging activity on the 1,1-diphenyl-2-picrylhydrazyl radical and inhibited lipid peroxidation in a methyl linoleate solution induced by 2,2'-azobis(2,4-dimethylvaleronitrile) (AMVN). However, veratrole-type urushiol derivatives did not scavenge or inhibit lipid peroxidation. CTUDs also acted as effective inhibitors of lipid peroxidation of the egg yolk phosphatidylcholine large unilamellar vesicle (PC LUV) liposome system induced by various radical generators such as AMVN, 2,2'-azobis(2-amidino-propane) dihydrochloride, and copper ions, although their efficiencies differed slightly. In addition, CTUDs suppressed formation of cholesteryl ester hydroperoxides in rat blood plasma induced with copper ions. CTUDs containing more than five carbon atoms in the alkyl chain showed excellent lipophilicity in a n-octanol/water partition experiment. These compounds also exhibited high affinities to the liposome membrane using the ultrafiltration method of the PC LUV liposome system. Therefore, CTUDs seem to act as efficient antioxidative compounds against membranous lipid peroxidation owing to their localization in the phospholipid bilayer. These results suggest that nonallergenic CTUDs act as antioxidants to protect against oxidative damage of cellular and subcellular membranes. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2014.03.041

文献信息

• Aromatic tetrahedral borate compounds for lubricating compositions
  申请人：THE LUBRIZOL CORPORATION

  公开号：US10336963B2

  公开（公告）日：2019-07-02

  A lubricating composition includes an oil of lubricating viscosity and an ionic tetrahedral borate compound which includes a cation and a tetrahedral borate anion which includes a boron atom, the boron atom having at least one aromatic bidentate di-oxo ligand. The compound may be represented by formula (I), where R1 and R2 are selected from C1-48 hydrocarbyl groups or together form a substituted or unsubstituted 5- or 6-membered ring; R3 and R4 together represent a substituted or unsubstituted aromatic ring; m is 0 or 1; X is hydrogen, a C1-24 hydrocarbyl group, —OR5, —NHR5, or ═O, R5 is a C1-24 hydrocarbyl group; M represents the cation; and n is at least 1. The cation may be selected to provide detergent and/or dispersant properties to the lubricating composition. In the case of ammonium cations, the molecular weight may be 260 g/mol or higher for providing a highly soluble compound, particularly when X is ═O.

  一种润滑组合物包括一种具有润滑粘度的油和一种离子型四面体硼酸盐化合物，该化合物包括一个阳离子和一个四面体硼酸盐阴离子，该阴离子包括一个硼原子，该硼原子具有至少一个芳香族双齿二氧配位体。该化合物可由式（I）表示，其中 R1 和 R2 选自 C1-48 羧基或共同形成取代或未取代的 5 或 6 元环；R3 和 R4 共同代表取代或未取代的芳环；m 为 0 或 1；X 为氢、C1-24 羧基、-OR5、-NHR5 或═O，R5 为 C1-24 羧基；M 代表阳离子；n 至少为 1。阳离子的选择可为润滑油组合物提供清洁剂和/或分散剂特性。在铵阳离子的情况下，分子量可为 260 克/摩尔或更高，以提供高溶解性化合物，特别是当 X 为 ═O 时。
• Direct synthesis of mono-glycosylated catechols from glycosylacetates or imidates using BF3.OEt2 as catalyst
  作者：Stéphane Mabic、Claude Benezra、Jean-Pierre Lepoittevin

  DOI：10.1016/0040-4039(93)88077-v

  日期：1993.7

  The coupling of 3-n-alkylcatechols to the acetate or trichloroimidate derivatives of beta-D- or alpha-D- sugars (glucose, galactose. xylose, mannose and maltose) catalysed by BF3.OEt2 has been studied. Beta sugars with an equatorial acetate group at position 2 formed exclusively beta adducts with yields of 60-80%. Alpha sugars with an equatorial acetate group at position 2 formed beta adducts, while beta sugars with an axial acetate group formed alpha adducts when activated as trichloroimidates, with yields of 70-85%. Two mechanisms to explain these results are proposed.
• YAMAGUCHI, ELAINE S.;LISTON, THOMAS V.
  作者：YAMAGUCHI, ELAINE S.、LISTON, THOMAS V.

  DOI：——

  日期：——
• Lubricating oil additive and lubricating oil composition containing the same
  申请人：CHEVRON RESEARCH AND TECHNOLOGY COMPANY

  公开号：EP0478857B1

  公开（公告）日：1994-02-16
• ALKYLAMINE COMPLEXES OF BORATED ALKYL CATECHOLS AND LUBRICATING OIL COMPOSITIONS CONTAINING THE SAME
  申请人：CHEVRON RESEARCH AND TECHNOLOGY COMPANY

  公开号：EP0491856A1

  公开（公告）日：1992-07-01