1-羟基-9-十八烷酮 | 173029-08-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-羟基-9-十八烷酮
• 英文名称: 1-hydroxy-9-octadecanone
• 英文别名: 1-hydroxyoctadecan-9-one
• CAS: 173029-08-8
• 化学式: C₁₈H₃₆O₂
• 分子量: 284.483
• InChiKey: XOCYZTHHCPHQQI-UHFFFAOYSA-N

物化性质

• 沸点：
  408.4±28.0 °C(Predicted)
• 密度：
  0.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-羟基-9-十八烷酮 在 jones' reagent 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 9-氧代十八烷酸
  参考文献：
  名称：

  Anti-inflammatory Constituents of the Red Alga Gracilaria verrucosa and Their Synthetic Analogues

  摘要：

  A chemical study on the anti-inflammatory components of the red alga Gracilaria verrucosa led to the isolation of new 11 -deoxyprostaglandins (1-4), a ceramide (5), and a C-16 keto fatty acid (6), along with known oxygenated fatty acids (7-14). Their structures were elucidated on the basis of NMR and MS data. The absolute configurations of compounds 1-5 were determined by Mosher's method. The anti-inflammatory activity of the isolated compounds (1-14) was evaluated by determining their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 9 and 10 exhibited the most potent activity. In the evaluation of these two compounds and derivatized analogues (15-40), the anti-inflammatory activity was enhanced in some synthetic analogues. These enone fatty acids were investigated as potential anti-inflammatory leads for the first time.

  DOI：

  10.1021/np070452q
• 作为产物：
  描述：

  (E)-9-oxooctadec-10-enol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 1-羟基-9-十八烷酮
  参考文献：
  名称：

  Anti-inflammatory Constituents of the Red Alga Gracilaria verrucosa and Their Synthetic Analogues

  摘要：

  A chemical study on the anti-inflammatory components of the red alga Gracilaria verrucosa led to the isolation of new 11 -deoxyprostaglandins (1-4), a ceramide (5), and a C-16 keto fatty acid (6), along with known oxygenated fatty acids (7-14). Their structures were elucidated on the basis of NMR and MS data. The absolute configurations of compounds 1-5 were determined by Mosher's method. The anti-inflammatory activity of the isolated compounds (1-14) was evaluated by determining their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-alpha) in lipopolysaccharide (LPS)-activated RAW 264.7 murine macrophage cells. Compounds 9 and 10 exhibited the most potent activity. In the evaluation of these two compounds and derivatized analogues (15-40), the anti-inflammatory activity was enhanced in some synthetic analogues. These enone fatty acids were investigated as potential anti-inflammatory leads for the first time.

  DOI：

  10.1021/np070452q

文献信息

• Practical and General Palladium-Catalyzed Synthesis of Ketones from Internal Olefins
  作者：Bill Morandi、Zachary K. Wickens、Robert H. Grubbs

  DOI：10.1002/anie.201209541

  日期：2013.3.4

  Make it simple! A convenient and general palladium‐catalyzed oxidation of internal olefins to ketones is reported. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed‐oil derivatives and a bioactive natural product (see scheme) are described, as well as intriguing mechanistic features.

  简单点！据报道，内烯烃可方便地通过钯催化氧化成酮。该转变在室温下发生，并显示出较宽的底物范围。描述了在种子油衍生物和生物活性天然产物（参见方案）的氧化中的应用，以及引人入胜的机械特性。
• PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20140194604A1

  公开（公告）日：2014-07-10

  The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C 2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.

  本发明涉及将内烯烃氧化为酮的方法。在各种实施方式中，每种方法包括将具有初始内烯烃的有机底物与（a）双阳离子钯盐的混合物；和（b）氧化剂接触，溶解或分散在溶剂体系中形成反应混合物，所述溶剂体系包括至少一种C2-6碳腈和可选地至少一种次烷基酰胺，所述方法在足以将初始内烯烃的至少50摩尔％转化为酮的条件下进行，所述酮位于初始内烯烃的碳上。该转化在室温下发生，并显示出广泛的底物范围。描述了将其应用于种子油衍生物和生物活性天然产物的氧化。
• Selective oxidation of primary-secondary diols with methyl hypochlorite in acid buffered medium
  作者：Patrick S.G. Tassignon、Dick de Wit、Theo C. de Rijk、Laurent F. De Buyck

  DOI：10.1016/0040-4020(95)00747-v

  日期：1995.10

  A convenient, low cost method was developed for the selective oxidation of secondary alcohols, leaving primary alcohol functions intact. Methyl hypochlorite, generated from chlorine or trichloroisocyanuric acid in methanol, is used as a ‘positive chlorine’ reagent in the presence of an appropriate buffer which is acidic enough to warrant good transfer of ‘positive chlorine’. 1,9(R)-octadecanediol was

  开发了一种方便，低成本的方法，用于仲醇的选择性氧化，而伯醇的功能保持不变。由氯或甲醇中的三氯异氰尿酸生成的次氯酸甲酯在适当的缓冲剂存在下用作“正氯”试剂，该缓冲剂的酸性足以确保“正氯”的良好转移。将1，9（R）-十八烷二醇以98％的选择性转化为1-羟基-9-十八烷酮。
• US9096519B2
  申请人：——

  公开号：US9096519B2

  公开（公告）日：2015-08-04
• [EN] METHOD FOR THE OXIDATION OF ALCOHOLS<br/>[FR] PROCEDE D'OXYDATION D'ALCOOLS
  申请人：INSTITUUT VOOR AGROTECHNOLOGISCH ONDERZOEK (ATO-DLO)

  公开号：WO1997011046A1

  公开（公告）日：1997-03-27

  (EN) A method is described for the oxidation of secondary alcohols by reaction of the alcohol with a chlorine or bromine compound in which the chlorine or bromine has a valency of + 1, the alcohol being allowed to react with the halogen compound in the presence of methanol or another primary or tertiary alkanol and in the presence of an acid buffer. In this way a very high secondary: primary oxidation selectivity is obtained, which leads to the preparation of 1-hydroxy-ketones such as 1-hydroxy-9-octadecanone and 1-hydroxy-12-octadecanone.(FR) L'invention porte sur un procédé d'oxydation d'alcools secondaires par réaction de l'alcool avec un composé de chlore ou de bromine, où le chlore ou le brome ont une valence de + 1, l'alcool pouvant réagir avec le composé d'halogène en présence de méthanol ou d'un autre alcanol primaire ou tertiaire et d'un tampon acide. Ainsi, une sélectivité d'oxydation secondaire: primaire très élevée est obtenue, laquelle conduit à la préparation de 1-hydroxy-cétones, telles que 1-hydroxy-9-octadécanone et 1-hydroxy-12-octadécanone.