2,6-dimethyl-5-oxo-heptanoic acid | 74457-59-3

• 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: 2,6-dimethyl-5-oxo-heptanoic acid
• 英文别名: 2,6-Dimethyl-5-oxo-heptansaeure；2,6-dimethyl-5-oxoheptanoic acid
• CAS: 74457-59-3
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: KFSWOOWOYKTCDK-UHFFFAOYSA-N

物化性质

• 沸点：
  171-175 °C(Press: 15 Torr)
• 密度：
  1.015±0.06 g/cm3(Predicted)
• 保留指数：
  2515

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-5-oxo-heptanoic acid 生成 2-甲基戊二酸
  参考文献：
  名称：

  Semmler, Chemische Berichte, 1904, vol. 37, p. 239

  摘要：

  DOI：
• 作为产物：
  描述：

  3-异丙基-6-甲基-2-环己烯-1-酮 在 potassium permanganate 、 水 作用下， 生成 2,6-dimethyl-5-oxo-heptanoic acid
  参考文献：
  名称：

  Tiemann; Semmler, Chemische Berichte, 1898, vol. 31, p. 2892

  摘要：

  DOI：

文献信息

• CUPRIC ION-CATALYZED DIOXYGENATION OF 1,2-CYCLOHEXANEDIONES. A NONENZYMATIC ANALOG FOR QUERCETINASE DIOXYGENATION
  作者：Masanori Utaka、Makoto Hojo、Yasuyuki Fujii、Akira Takeda

  DOI：10.1246/cl.1984.635

  日期：1984.4.5

  1,2-Cyclohexanediones were found to be dioxygenated by molecular oxygen with the aid of cupric ion to afford 1,5-keto acids and carbon monoxide. The reaction proceeds possibly via an endoperoxide intermediate. Methyl α-hydroxyadipates were also formed as byproducts. The mechanism of oxygenation is discussed.

  1,2-环己二酮被发现能够在铜离子的辅助下被分子氧双氧合，生成1,5-酮酸和一氧化碳。反应可能通过一个内过氧化物中间体进行。同时，也生成了作为副产物的甲基α-羟基己二酸酯。氧化的机制被讨论。
• Novel method for converting dihydrotagetone, a bifuctional acyclic monoterpene ketone, isolated from the plant species of tagetes, into a coconut flavoured two chiral centered compound 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone as a novel analogue of natural whisky lactone and coconut aldehyde
  申请人：——

  公开号：US20020137949A1

  公开（公告）日：2002-09-26

  A natural inexpensive acyclic monoterpene ketone (dihydrotagetone) of formula (4), isolated from the oil of Tagetes sp., was smoothly oxidized with metaperiodate/potassium permanganate into 2,6-dimethyl-4-oxo-heptanoic acid of formula (3), the reduction of 3 with metal hydride such as sodium borohydride or lithium aluminium hydride provided 4-hydroxyacid of formula (2) which on without isolation undergone lactonisation in acidic medium furnished two chiral centered 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone of formula (1) as an analogue of whisky lactone 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1a) responsible for high quality of alcoholic beverage (whisky, wine, brandy and scotch), in addition, coconut flavoured 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1) is also as an analogue of coconut aldehyde (&ggr;-nonalactone, F.E.M.A. No. 2751) of formula (1b) which is responsible for flavouring a wide range of food stuffs including baked goods and confectionery.

  从Tagetes sp.的油中分离出的一种天然廉价无环单萜酮（二氢紫菀酮）的化学式（4），经过与高碘酸钾/高锰酸钾的平稳氧化反应，得到了化学式（3）的2,6-二甲基-4-氧代庚酸。将3还原为金属氢化物（如硼氢化钠或铝锂氢化物）可以得到化学式（2）的4-羟基酸。在酸性介质中，化学式（2）的内酯化反应未经分离，生成了两个手性中心的5-异丁基-3-甲基-4,5-二氢-2（3H）-呋喃酮，化学式为（1），作为威士忌呋喃酮5-丁基-4-甲基-4,5-二氢-2（3H）-呋喃酮的类似物，后者是高质量酒类（威士忌，葡萄酒，白兰地和苏格兰威士忌）的重要成分之一。此外，化学式（1）的椰子风味的5-丁基-4-甲基-4,5-二氢-2（3H）-呋喃酮也是椰子醛（&ggr;-壬内酯，F.E.M.A.编号2751）的类似物，后者是调味各种食品，包括糕点和糖果的重要成分之一。
• Micellar catalysis in the base-catalyzed autoxidation of diosphenol
  作者：Masanori Utaka、Seishiro Matsushita、Haruhiro Yamasaki、Akira Takeda

  DOI：10.1016/s0040-4039(00)78839-3

  日期：1980.1

  The base-catalyzed autoxidation of diosphenol was catalyzed by cationic micelles with a remarkable selectivity to give an 1,5-keto acid by a mechanism analogous to the oxygenation of quercetin or 3-hydroxyflavones.

  阳离子胶束具有很强的选择性，通过与槲皮素或3-羟基黄酮的氧化作用机理，可以选择性催化碱催化的二酚的自氧化。
• Heptanonic acid and furanone compounds and compositions
  申请人：Council of Scientific & Industiral Research

  公开号：US20030212281A1

  公开（公告）日：2003-11-13

  A natural inexpensive acyclic monoterpene ketone (dihydrotagetone) of formula (4), isolated from the oil of Tagetes sp., was smoothly oxidized with meta-periodate/potassium permanganate into 2,6-dimethyl-4-oxo-heptanoic acid of formula (3), the reduction of 3 with metal hydride such as sodium borohydride or lithium aluminium hydride provided 4-hydroxyacid of formula (2) which on without isolation undergone lactonisation in acidic medium furnished two chiral centered 5-isobutyl-3-methyl-4,5-dihydro-2(3H)-furanone of formula (1) as an analogue of whisky lactone 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1a) responsible for high quality of alcoholic beverage (whisky, wine, brandy and scotch), in addition, coconut flavoured 5-butyl-4-methyl-4,5-dihydro-2(3H)-furanone of formula (1) is also as an analogue of coconut aldehyde (&ggr;-nonalactone, F.E.M.A. No. 2751) of formula (1b) which is responsible for flavouring a wide range of food stuffs including baked goods and confectionery.

  从Tagetes sp.的油中分离出的一种天然廉价的无环单萜酮（二氢龙蒿酮）（式（4）），经过与甲苯磺酸亚铁/高锰酸钾的平滑氧化反应，形成了式（3）的2,6-二甲基-4-氧代庚酸。将3与金属氢化物（如硼氢化钠或铝锂氢化物）还原，得到式（2）的4-羟基酸，它在酸性介质中经过内酯化反应，生成两个手性中心的5-异丁基-3-甲基-4,5-二氢-2（3H）-呋喃酮（式（1））作为威士忌内酯5-丁基-4-甲基-4,5-二氢-2（3H）-呋喃酮（式（1a））的类似物，负责酒类饮料（威士忌、葡萄酒、白兰地和苏格兰威士忌）的高品质。此外，椰子风味的5-丁基-4-甲基-4,5-二氢-2（3H）-呋喃酮（式（1））也是椰子醛（&ggr;-壬内酯，F.E.M.A. No. 2751）（式（1b））的类似物，负责为包括烘焙食品和糖果在内的各种食品提供风味。
• Wallach; Collmann; Thede, Justus Liebigs Annalen der Chemie, 1903, vol. 327, p. 135
  作者：Wallach、Collmann、Thede

  DOI：——

  日期：——