5-methylenetetradecanoic acid | 98498-92-1

• 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: 5-methylenetetradecanoic acid
• 英文别名: 5-nonyl-5-hexanoic acid；5-Methylene-tetradecanoic acid；5-methylidenetetradecanoic acid
• CAS: 98498-92-1
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: KEVNKFRDSLODAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  5-methylenetetradecanoic acid 在 四氧化锇 咪唑 、 叔丁基过氧化氢 、 四乙基醋酸铵 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 草酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 16.5h， 生成 5-methylene-5-t-butyldimethylsilyloxymethyl-5-tetradecanolide
  参考文献：
  名称：

  An Efficient Synthetic Method for (±)-Malyngolide and Its Optical Resolution

  摘要：

  描述了一种来自海洋蓝绿藻 Lyngbya majuscula GOMONT 的抗生素 (±)-malyngolide (1) 的便捷合成方法。以2-甲基戊二酸酐为原料，分四步合成了化合物(±)-1，其中以TBHP为基础的锇催化不饱和羧酸中亚甲基单元的邻位二羟基化过程为关键步骤。 (±)-1的光学拆分通过HPLC完成，其中(±)-1的非对映体(+)-2-(4-氯苯基)异戊酸[(+)-CPIA]酯衍生自(+)- CPIA-C1 可以很容易地分离，随后每种酯的水解分别得到对映体纯的 (−)-l 和 (+)-l。还描述了α-亚甲基马林高内酯的合成方法，其具有预期的生物活性。

  DOI：

  10.1080/00021369.1985.10866953
• 作为产物：
  描述：

  1-溴壬烷 在 氢氧化钾 、 氨 、 lithium 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 144.0~146.0 ℃ 、66.66 Pa 条件下， 反应 192.67h， 生成 5-methylenetetradecanoic acid
  参考文献：
  名称：

  Carbon-carbon bond fragmentation through oxidative electrolysis of carboxylic acids and its application to the synthesis of malyngolide

  摘要：

  DOI：

  10.1021/jo00364a053

文献信息

• Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes
  申请人：McDaniel C. Steven

  公开号：US20100210745A1

  公开（公告）日：2010-08-19

  Disclosed herein are polymeric materials such as a coating, a plastic, a laminate, a composite, an elastomer, an adhesive, or a sealant; a surface treatment such as a textile finish or a wax; a filler for such a polymeric material or a surface treatment that includes an enzyme such as an esterase (e.g., a lipolytic enzyme, a sulfuric ester hydrolase, an organophosphorus compound degradation enzyme), an enzyme (e.g., a lysozyme, a lytic transglycosylase) that degrades a cell wall and/or a cell membrane component, a biocidal or biostatic peotide, and/or a peptidase. Also disclosed herein are methods of altering a material's property such as service life, flexability, or rigidity, by incorporation of an enzyme into a material capable of being chemically crosslinked by the activity of a lipolytic enzyme, a hydrolase, and/or a urease.

  本文公开了一些聚合材料，如涂层、塑料、层压板、复合材料、弹性体、粘合剂或密封剂；一种表面处理，如纺织品涂层或蜡；一种填料，用于这样的聚合材料或表面处理，其中包括一种酶，如酯酶（例如，脂肪水解酶，硫酸酯水解酶，有机磷化合物降解酶），降解细胞壁和/或细胞膜成分的酶（例如，溶菌酶，裂解转糖基酶），生物杀菌或生物静态肽，以及/或肽酶。本文还公开了通过将酶纳入可通过脂肪水解酶、水解酶和/或脲酶的活性交联材料中来改变材料性能，如使用寿命、柔韧性或刚度的方法。
• Anti-fouling Paints and Coatings
  申请人：Reactive Surfaces LTD

  公开号：US20150191607A1

  公开（公告）日：2015-07-09

  Disclosed herein are polymeric materials such as a coating, a plastic, a laminate, a composite, an elastomer, an adhesive, or a sealant; a surface treatment such as a textile finish or a wax; a filler for such a polymeric material or a surface treatment that includes an enzyme such as an esterase (e.g., a lipolytic enzyme, a sulfuric ester hydrolase, an organophosphorus compound degradation enzyme), an enzyme (e.g., a lysozyme, a lytic transglycosylase) that degrades a cell wall and/or a cell membrane component, a biocidal or biostatic peptide, and/or a peptidase. Also disclosed herein are methods of altering a material's property such as service life, flexability, or rigidity, by incorporation of an enzyme into a material capable of being chemically crosslinked by the activity of a lipolytic enzyme, a hydrolase, and/or a urease.

  本文披露了聚合材料，例如涂层、塑料、层压材料、复合材料、弹性体、粘合剂或密封剂；表面处理，例如纺织品整理或蜡；填充剂，用于这种聚合材料或表面处理，包括酯酶（例如脂肪水解酶、硫酸酯水解酶、有机磷化合物降解酶）的酶，降解细胞壁和/或细胞膜成分的酶（例如溶菌酶、裂解转葡糖苷酶），生物杀菌或生物稳定肽，和/或肽酶。本文还披露了通过将酶并入能够通过脂肪水解酶、水解酶和/或脲酶的活性进行化学交联的材料中，改变材料性能（例如使用寿命、柔韧性或刚度）的方法。
• The Role of Ni-Carboxylate During Catalytic Asymmetric Iodolactonization Using PyBidine-Ni(OAc)2
  作者：Takayoshi Arai、Satoshi Kajikawa、Eri Matsumura

  DOI：10.1055/s-0033-1339676

  日期：——

  The combination of a PyBidine-Ni(OAc)(2) complex with a catalytic amount of iodine efficiently catalyzed asymmetric iodolactonization to generate chiral iodolactones with up to 89% enantiomeric excess. The formation of an intermediate Ni-carboxylate species from the alkenyl carboxylic acid is a key role in promoting the iodolactonization.
• Carbon-carbon bond fragmentation through oxidative electrolysis of carboxylic acids and its application to the synthesis of malyngolide
  作者：Peter G. M. Wuts、Minn Chang Cheng

  DOI：10.1021/jo00364a053

  日期：1986.7
• An Efficient Synthetic Method for (±)-Malyngolide and Its Optical Resolution
  作者：Kozo Machiya、Itsuo Ichimoto、Kennosuke Tonari、Mitsunori Kirihata、Hiroo Ueda

  DOI：10.1080/00021369.1985.10866953

  日期：1985.6

  A convenient synthetic method for (±)-malyngolide (1), an antibiotic from the marine bluegreen alga Lyngbya majuscula GOMONT, is described. The compound (±)-1 was synthesized from 2-methylglutaric anhydride (starting material) in four steps, involving the TBHP-based osmium-catalyzed procedure for vicinal dihydroxylation of the methylene unit in unsaturated carboxylic acid as the key step. The optical resolution of (±)-l was accomplished by HPLC, in which diastereomeric (+)-2-(4-chlorophenyl)isovaleric acid [(+)-CPIA] esters of (±)-l derived from (+)-CPIA-C1 could be easily separated, and subsequent hydrolysis of each ester gave the enantiomeri-cally pure (−)-l and (+)-l, respectively. A synthetic method for α-methylene malyngolide, which is to be expected for biological activity, is also described.

  描述了一种来自海洋蓝绿藻 Lyngbya majuscula GOMONT 的抗生素 (±)-malyngolide (1) 的便捷合成方法。以2-甲基戊二酸酐为原料，分四步合成了化合物(±)-1，其中以TBHP为基础的锇催化不饱和羧酸中亚甲基单元的邻位二羟基化过程为关键步骤。 (±)-1的光学拆分通过HPLC完成，其中(±)-1的非对映体(+)-2-(4-氯苯基)异戊酸[(+)-CPIA]酯衍生自(+)- CPIA-C1 可以很容易地分离，随后每种酯的水解分别得到对映体纯的 (−)-l 和 (+)-l。还描述了α-亚甲基马林高内酯的合成方法，其具有预期的生物活性。