5,9-dimethyldeca-2,4,8-trienoic acid ethyl ester | 106925-10-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5,9-dimethyldeca-2,4,8-trienoic acid ethyl ester
• 英文别名: ethyl 5,9-dimethyl-2E,4,8-decatrienoate
• CAS: 106925-10-4
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: OUMILASNGJWLED-WJJPMBIOSA-N

物化性质

• 沸点：
  311.4±21.0 °C(Predicted)
• 密度：
  0.912±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5,9-dimethyldeca-2,4,8-trienoic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以20.65 g的产率得到5,9-dimethyldeca-2,4,8-trienoic acid
  参考文献：
  名称：

  Citral derived amides as potent bacterial NorA efflux pump inhibitors

  摘要：

  Monoterpene citral and citronellal have been used as starting material for the preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid amides and 9-formyl-5-methyl-deca-2,4,8-trienoic acid amides. The amides on bioevaluation as efflux pump inhibitors (EPIs) against Staphylococcus aureus 1199 and NorA overexpressing S. aureus 1199B bacteria resulted in the identification of several of these as potent EPIs. Many of these amides have been shown to possess potency higher or equivalent to known EPIs such as reserpine, verapamil, carsonic acid, and piperine. In this communication, we report a convenient synthesis of alkenyl amides, their bioevaluation and identification as efflux pump inhibitors against S. aureus. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.030
• 作为产物：
  描述：

  磷酰基乙酸三乙酯 、 柠檬醛 生成 5,9-dimethyldeca-2,4,8-trienoic acid ethyl ester
  参考文献：
  名称：

  Direction of epoxidation of esters of polyunsaturated acids

  摘要：

  DOI：

  10.1007/bf01108225

文献信息

• Studies of the use of elemento-organic compounds of the fifteenth and sixteenth groups in organic synthesis LXXI. Reaction of α-halogeno carboxylic derivatives with carbonyl compounds promoted by tributylstibine
  作者：Yao-Zeng Huang、Chen Chen、Yanchang Shen

  DOI：10.1016/0022-328x(89)87318-8

  日期：1989.4

  α,β-Unsaturated esters and amides were conveniently obtained from the trialkylstibine-promoted reaction of α-halogenocarboxylic derivatives with carbonyl compounds. In this reaction, a quaternary stibonium salt is an active intermediate that can be trapped and can undergo further reaction with the substrate.

  从α-卤代羧酸衍生物与羰基化合物的三烷基苯乙烯促进的反应中方便地获得α，β-不饱和酯和酰胺。在该反应中，季sti盐是一种活性中间体，可以被捕获并与底物进行进一步反应。
• Organic synthesis using haloboration reaction xv. A new synthesis of α,β-unsaturated esters by the highly chemoselective reaction of B-I-9-BBN-ethoxyethyne adduct with aldehydes
  作者：Yoshitaka Satoh、Takao Tayano、Shoji Hara、Akira Suzuki

  DOI：10.1016/s0040-4039(01)93472-0

  日期：——

  A haloboration adduct, formed by the reaction of B-iodo-9-borabicyclo[3.3.1]nonanes with ethoxyethyne reacts with aldehydes chemoselectively under very mild conditions. The subsequent hydrolytic work-up affords -α,β-unsaturated esters in good yields.

  B-碘-9-硼环[3.3.1]壬烷与乙氧基乙炔的反应形成的卤代加合物在非常温和的条件下与醛发生化学选择性反应。随后的水解后处理以良好的产率得到-α，β-不饱和酯。
• Herrmann, Wolfgang A.; Wang, Mei, Angewandte Chemie, 1991, vol. 103, # 12, p. 1709 - 1711
  作者：Herrmann, Wolfgang A.、Wang, Mei

  DOI：——

  日期：——
• Acyclic isoprenoid ?,?-enals in the Doebner and Knoevenagel reactions with monoethyl malonate
  作者：A. G. Nigmatov、�. P. Serebryakov

  DOI：10.1007/bf00959576

  日期：1990.3