1,1,1-三氟-2-十五烷酮 | 81123-99-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1,1-三氟-2-十五烷酮
• 中文别名: 1,1,1-氟十三五烷-2-酮
• 英文名称: 1,1,1-trifluoropentadecan-2-one
• 英文别名: 2-Pentadecanone, 1,1,1-trifluoro-
• CAS: 81123-99-1
• 化学式: C₁₅H₂₇F₃O
• 分子量: 280.374
• InChiKey: KHVKUGBUCSPTEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1,1-三氟-2-十五烷酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 1,1,1-Trifluoropentadecan-2-ol
  参考文献：
  名称：

  Highly enantioselective synthesis of long chain alkyl trifluoromethyl carbinols and β-thiotrifluoromethyl carbinols through lipases

  摘要：

  Among a variety of lipases tested, Candida antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl trifluoromethyl carbinols 1a-4a and beta-thiotrifluoromethyl carbinols 5a-7a, producing both R and S enantiomeric alcohols in good to excellent chemical yield and enantioselectivity. In all cases the lipase preferentially acylates the S enantiomer, irrespective the presence or not of a sulfur atom in beta position to the hydroxyl group, When the reaction was carried out on the non-fluorinated substrates 1c-2c, the process occurred much faster and with higher e.e. of the less reacting enantiomer than when conducted on the fluorinated substrates. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00256-x
• 作为产物：
  描述：

  1,3-dioxoisoindolin-2-yl tetradecanoate 在 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 双氧水 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 28.5h， 生成 1,1,1-三氟-2-十五烷酮
  参考文献：
  名称：

  通过控制有机硼酸酯配合物的反应性来多样化合成氟代烷基酮

  摘要：

  在此，我们报道了通过容易获得的有机硼酸酯和氟烷基酰基硅烷之间的可见光诱导反应来合成氟烷基酮。对原位生成的有机硼酸盐配合物的反应性进行选择性控制是实现不同转化的关键。在碱性条件下，有机硼酸酯配合物经历脱硼氟化物消除，导致形成烯醇甲硅烷基醚作为中间体，其与各种亲电试剂反应生成脱氟酮作为产物。此外，与过氧化物结合，氟烷基的1,2-位移比脱硼氟化物消除更有利于生成缩酮中间体，从而形成酮作为产物。这种无过渡金属的反应操作简单，芳基、烯基和烷基硼酸酯都是合适的底物。克级反应和生物活性分子（包括齐氟硅氧烷及其氟烷基类似物）的简便合成已经证明了其合成潜力。

  DOI：

  10.1021/jacs.3c12150

文献信息

• Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: A probe of structural and conformational features contributing to inhibition
  作者：Dale L. Boger、Haruhiko Sato、Aaron E. Lerner、Bryce J. Austin、Jean E. Patterson、Matthew P. Patricelli、Benjamin F. Cravatt

  DOI：10.1016/s0960-894x(98)00734-3

  日期：1999.1

  The examination of a series of trifluoromethyl ketone inhibitors of Fatty Acid Amide Hydrolase (FAAH, oleamide hydrolase, anandamide amidohydrolase) is detailed in efforts that define structural and conformational properties that contribute to enzyme inhibition and substrate binding. The results imply an extended bound conformation, highlight a role for the presence, position, and stereochemistry of

  在确定有助于酶抑制和底物结合的结构和构象特性的努力中，详细检查了一系列脂肪酸酰胺水解酶的三氟甲基酮抑制剂（FAAH，油酰胺水解酶，阿南酰胺酰胺水解酶）。结果暗示了扩展的结合构象，突出了δ-顺式双键的存在，位置和立体化学的作用，并且暗示了脂肪酸酰胺底物的C11-C18 / C22几乎没有明显的作用。
• New Methodology toward α,β-Unsaturated Carboxylic Acids from Saturated Acids
  作者：Qingjiang Li、Gregory P. Tochtrop

  DOI：10.1021/ol500127u

  日期：2014.3.7

  A carefully designed three-step unsaturation of carboxylic acids is described. Briefly, carboxylic acids were converted to the trifluoromethyl ketone. Subsequent treatment with selenium dioxide followed by hydrolysis afforded α,β-unsaturated carboxylic acids. The mechanism of the reported transformation was investigated, which led us to propose a novel explanation featuring selenium dioxide assisted

  描述了精心设计的三步羧酸不饱和键。简而言之，将羧酸转化为三氟甲基酮。随后用二氧化硒处理，然后水解，得到α，β-不饱和羧酸。研究了报道的转化的机理，这使我们提出了一种新颖的解释，其特征是二氧化硒辅助的三氟甲基酮的烯醇化，然后进行β-去质子化。
• Direct Preparation of Trifluoromethyl Ketones from Carboxylic Esters: Trifluoromethylation with (Trifluoromethyl)trimethylsilane
  作者：Jürgen Wiedemann、Thomas Heiner、Gregorz Mloston、G. K. Surya Prakash、George A. Olah

  DOI：10.1002/(sici)1521-3773(19980403)37:6<820::aid-anie820>3.0.co;2-m

  日期：1998.4.3

  Previously difficult to prepare, aliphatic and alicyclic trifluoromethylketones (e.g. 1 and 2), which are of pharmacalogic interest as potential enzyme inhibitors, can now be synthesized easily and efficiently. The one-step reaction starting with carbonic esters and trimethyl(trifluoromethyl)silane is induced by tetrabutylammonium fluoride in nonpolar, aprotic solvents and proceeds without formation of double-addition products.
• 10.1016/j.bioorg.2024.107453
  作者：Cai, Nan、Gao, Xiang、Li, Wenjing、Yang, Li、Zhao, Jinfeng、Qu, Jingping、Zhou, Yuhan

  DOI：10.1016/j.bioorg.2024.107453

  日期：——
• Highly enantioselective synthesis of long chain alkyl trifluoromethyl carbinols and β-thiotrifluoromethyl carbinols through lipases
  作者：Inés Petschen、Edi A. Malo、M.P. Bosch、Angel Guerrero

  DOI：10.1016/0957-4166(96)00256-x

  日期：1996.7

  Among a variety of lipases tested, Candida antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl trifluoromethyl carbinols 1a-4a and beta-thiotrifluoromethyl carbinols 5a-7a, producing both R and S enantiomeric alcohols in good to excellent chemical yield and enantioselectivity. In all cases the lipase preferentially acylates the S enantiomer, irrespective the presence or not of a sulfur atom in beta position to the hydroxyl group, When the reaction was carried out on the non-fluorinated substrates 1c-2c, the process occurred much faster and with higher e.e. of the less reacting enantiomer than when conducted on the fluorinated substrates. Copyright (C) 1996 Elsevier Science Ltd