(2E)-5,9-dimethyldeca-2,8-dienoyl chloride | 151510-76-8

• 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: (2E)-5,9-dimethyldeca-2,8-dienoyl chloride
• CAS: 151510-76-8
• 化学式: C₁₂H₁₉ClO
• 分子量: 214.735
• InChiKey: QCEKQKSAPSWJEY-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2E)-5,9-dimethyldeca-2,8-dienoyl chloride 生成 (2E)-5,9-dimethyl-1-piperidin-1-yldeca-2,8-dien-1-one
  参考文献：
  名称：

  VIG B.; KANWAR R.; DAHIYA S. S., J. INDIAN CHEM. SOC., 1979, 56, NO 9, 935-937

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-5,9-dimethyl-deca-2,8-dienoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2E)-5,9-dimethyldeca-2,8-dienoyl chloride
  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

文献信息

• Palladium-catalyzed decarbonylative coupling of acid chlorides, organodisilanes, and 1,3-dienes
  作者：Yasushi Obora、Yasushi Tsuji、Takashi Kawamura

  DOI：10.1021/ja00075a089

  日期：1993.11
• 1,4-Carbosilylation of 1,3-Dienes via Palladium Catalyzed Three-Component Coupling Reaction
  作者：Yasushi Obora、Yasushi Tsuji、Takashi Kawamura

  DOI：10.1021/ja00144a005

  日期：1995.10

  Three-component coupling reaction of acid chlorides, organodisilanes, and 1,3-dienes achieves 1,4-carbosilylation of the 1,3-dienes to afford allylic silanes as the product. Bis(dibenzylideneacetone)palladium, a naked Pd(0) complex without donating ligand, showed high catalytic activity. A carbon and a silicon substituent are introduced at 1- and 4-positions of the 1,3-dienes regio- and stereoselectively with concomitant decarbonylation of the acid chlorides. A wide variety of allylic silanes are synthesized in high yields from these easily accessible substrates. On the other hand, a bully acid chloride such as adamantane-1-carboxylic acid chloride did not undergo the decarbonylation reaction but afforded allylic silanes containing acyl functionality. In all these reactions, transmetalation of the disilanes with eta(3)-allylchloropalladium intermediates might be a critical step in the catalytic cycle. As a model reaction for the transmetalation, reaction of di-mu-chlorobis[(1,2,3-eta)-4-phenyl-2-butenyl]dipalladium with disilanes was carried out. Although intermediate eta(3)-allylsilylpalladium species could not be detected, the corresponding allylic silanes, silyl chlorides, and Pd(0) metal were formed during the reaction. Furthermore, a similar three-component coupling reaction using aryl iodides, organosilylstannanes, and dienes also proceeded. However, the selectivity and the yield decreased considerably.
• Vig,B. et al., Journal of the Indian Chemical Society, 1979, vol. 56, p. 935 - 937
  作者：Vig,B. et al.

  DOI：——

  日期：——