α,α-difluorododecanoic acid | 502497-41-8

• 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: α,α-difluorododecanoic acid
• 英文别名: 2,2-difluorododecanoic acid；alpha,alpha-Difluorododecanoic acid
• CAS: 502497-41-8
• 化学式: C₁₂H₂₂F₂O₂
• 分子量: 236.302
• InChiKey: BYASAOXIJCOZBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α,α-difluorododecanoic acid 在 三氟化溴 作用下， 以60%的产率得到1,1,1-trifluoroundecane
  参考文献：
  名称：

  Constructing the CF3 group; unique trifluorodecarboxylation induced by BrF3

  摘要：

  A variety of 2-alkyl-1,3-dithiane-2-carboxylic acids was prepared from the appropriate alkyl halides, 1,3-dithiane and CO2. These acids were reacted with BrF3 to form the trifluoromethylalkyl derivatives via a combination of ionic and radical trifluorodecarboxylation in about 50-60% yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.063
• 作为产物：
  描述：

  2-decyl-2-ethoxycarbonyl-1,3-dithiane 在 氢氧化钾 、 三氟化溴 作用下， 以 乙醇 、 一氟三氯甲烷 为溶剂， 生成 α,α-difluorododecanoic acid
  参考文献：
  名称：

  A Novel Method for the Preparation of α,α‘-Difluoroesters and Acids Using BrF₃

  摘要：

  Alkyl-, haloalkyl-, and ketoalkyl-2-ethoxycarbonyl-1,3-dithianes were easily made from the appropriate primary or secondary alkyl bromides, 1,3-dithiane, and ethyl chloroformate. They were reacted with BrF3 to form the corresponding alpha,alpha-difluoro esters in 65-75% yield. Reaction conditions are very mild (1-2 min, 0 degreesC). The two sulfur atoms of the dithiane are essential for the reaction.

  DOI：

  10.1021/jo034829i

文献信息

• Autoinducer compounds
  申请人：The Research & Development Institute, Inc.

  公开号：US06337347B1

  公开（公告）日：2002-01-08

  Autoinducer compounds which enhance gene expression in a wide variety of microorganisms, therapeutic compositions and therapeutic methods wherein gene expression within microorganisms is regulated are disclosed.

  自动诱导化合物可以增强各种微生物的基因表达，公开了基因表达在微生物内部受到调控的治疗组合物和治疗方法。
• Radical Reaction Using an Organocopper Reagent Derived from Ethyl Bromodifluoroacetate
  作者：Kazuyuki Sato、Yuko Ogawa、Misato Tamura、Mika Harada、Terumasa Ohara、Masaaki Omote、Akira Ando、Itsumaro Kumadaki

  DOI：10.1135/cccc20021285

  日期：——

  In our previous work, reaction of ethyl bromodifluoroacetate (1) in the presence of Cu powder with olefins activated by an electron-withdrawing group gave the Michael-type adducts through an anionic intermediate. The same reaction with non-activated olefins was found to give addition products by a radical mechanism. The radical intermediate from α-methylstyrene was stabilized by a benzene ring and gave novel dimerization products. This reaction with 1-decene provided a convenient route to 2,2-difluorododecanoic acid.

  在我们之前的工作中，乙基溴二氟乙酸酯（1）在Cu粉的存在下与由电子吸引基团激活的烯烃反应，通过阴离子中间体形成Michael型加合物。发现使用未激活的烯烃进行相同反应会通过自由基机理形成加成产物。α-甲基苯乙烯的自由基中间体由苯环稳定并产生新的二聚产物。这种反应与1-癸烯提供了制备2,2-二氟十二酸的便捷途径。