2,2-双(三氟甲基)丙酸 | 45048-36-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,2-双(三氟甲基)丙酸
• 英文名称: 3,3,3-trifluoro-2-(trifluoromethyl)-2-methyl-propanoic acid
• 英文别名: 2,2-bis(trifluoromethyl)propionic acid；hexafluoropivalic acid；2,2 Bis (trifluoromethyl) Propionic Acid；α-Methylhexafluoro-isobuttersaeure；3,3,3-trifluoro-2-methyl-2-(trifluoromethyl)propanoic acid
• CAS: 45048-36-0
• 化学式: C₅H₄F₆O₂
• mdl: MFCD00236083
• 分子量: 210.076
• InChiKey: OIUKKVROQZMVDV-UHFFFAOYSA-N

物化性质

• 密度：
  1,479 g/cm3
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R34
• 海关编码：
  2915900090
• 危险品运输编号：
  3265

反应信息

• 作为反应物：
  描述：

  2,2-双(三氟甲基)丙酸 、 (R)-(-)-alpha-(三氟甲基)苄胺 在 N-甲基咪唑 、 甲基磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(R)-2,2-ditrifluoromethyl-N-(2,2,2-trifluoro-1-phenylethyl)-propanamide
  参考文献：
  名称：

  Rational application of self-disproportionation of enantiomers via sublimation—a novel methodological dimension for enantiomeric purifications

  摘要：

  The preliminary results presented in this work show that an enantiomer purification approach based on SDE via sublimation can be extended to non-volatile liquid compounds such as alpha-(phenyl)ethylamine and its beta-fluoro-derivatives by way of their rational modification with a sublimation enabling tag. 3,3,3-Trifluoro-2-(trifluoromethyl)-2-methyl-propanoic acid was found to perfectly serve the role of such a modifying tag. Thus, the corresponding amides derived from the amines and the fluorinated propanoic acid were highly crystalline and reasonably volatile compounds allowing for their sublimation at room temperature under normal pressure. All of these derivatives showed substantial self-disproportionation of enantiomers (SDEs) via sublimation under kinetic conditions (on a Petri dish in the open air). These preliminary results serve as a proof of a new principle that may extend the generality of enantiomer purification via sublimation to various organic compounds with physico-chemical properties of which render them otherwise unsuitable for a sublimation procedure. In particular, the very attractive cost structure of sublimation procedure renders this approach of potentially high practical and economic efficiency. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.040

文献信息

• TRIAZINE COMPOUNDS AND PHARMACEUTICAL USE THEREOF
  申请人：Japan Tobacco Inc.

  公开号：US20150266834A1

  公开（公告）日：2015-09-24

  Provided is a compound having an mPGES-1 inhibitory activity and useful for the prophylaxis or treatment of pain, rheumatism, osteoarthritis, fever, Alzheimer's disease, multiple sclerosis, arteriosclerosis, glaucoma, ocular hypertension, ischemic retinal disease, systemic scleroderma and cancer including colorectal cancer. A compound represented by the formula [I] or a pharmaceutically acceptable salt thereof: wherein each symbol is as defined in the SPECIFICATION.

  提供一种具有mPGES-1抑制活性的化合物，可用于预防或治疗疼痛、风湿病、骨关节炎、发热、阿尔茨海默病、多发性硬化症、动脉硬化、青光眼、眼压增高、缺血性视网膜疾病、全身性硬皮病和包括结肠癌在内的癌症。该化合物由式[I]表示，或其药用可接受的盐：其中每个符号如规范中定义。
• Discovery of N-(3-(morpholinomethyl)-phenyl)-amides as potent and selective CB2 agonists
  作者：Karin Worm、Damian G. Weaver、Rosalyn C. Green、Christopher T. Saeui、Doreen-Marie S. Dulay、William M. Barker、Joel A. Cassel、Gabriel J. Stabley、Robert N. DeHaven、Christopher J. LaBuda、Michael Koblish、Bernice L. Brogdon、Steven A. Smith、Roland E. Dolle

  DOI：10.1016/j.bmcl.2009.07.057

  日期：2009.9

  benzamides were identified as a novel series of cannabinoid receptor ligands. Replacing the sulfonamide functionality and reversing the original carboxamide bond led to the discovery of N-(3-(morpholinomethyl)-phenyl)-amides as potent and selective CB2 agonists. Selective CB2 agonist 31 (Ki = 2.7; CB1/CB2 = 190) displayed robust activity in a rodent model of postoperative pain.

  最近，氨磺酰基苯甲酰胺被确定为一系列新的大麻素受体配体。取代磺酰胺官能团并逆转原始的羧酰胺键导致发现N-（3-（吗啉代甲基）-苯基）-酰胺作为有效的和选择性的CB 2激动剂。选择性CB 2激动剂31（K i  = 2.7； CB 1 / CB 2  = 190）在术后疼痛的啮齿动物模型中显示出强大的活性。
• Benzazepinone Nav1.7 blockers: Potential treatments for neuropathic pain
  作者：Scott B. Hoyt、Clare London、Hyun Ok、Edward Gonzalez、Joseph L. Duffy、Catherine Abbadie、Brian Dean、John P. Felix、Maria L. Garcia、Nina Jochnowitz、Bindhu V. Karanam、Xiaohua Li、Kathryn A. Lyons、Erin McGowan、D. Euan MacIntyre、William J. Martin、Birgit T. Priest、McHardy M. Smith、Richard Tschirret-Guth、Vivien A. Warren、Brande S. Williams、Gregory J. Kaczorowski、William H. Parsons

  DOI：10.1016/j.bmcl.2007.09.032

  日期：2007.11

  A series of benzazepinones were synthesized and evaluated as hNa(v)1.7 sodium channel blockers. Several compounds from this series displayed good oral bioavailability and exposure and were efficacious in a rat model of neuropathic pain.

  合成了一系列苯并ze庚酮，并将其评估为hNa（v）1.7钠通道阻滞剂。该系列中的几种化合物具有良好的口服生物利用度和暴露能力，并且在神经性疼痛的大鼠模型中有效。
• Novel sulfamoyl benzamides as selective CB2 agonists with improved in vitro metabolic stability
  作者：Ian Sellitto、Bertrand Le Bourdonnec、Karin Worm、Allan Goodman、Markku A. Savolainen、Guo-Hua Chu、Christopher W. Ajello、Christopher T. Saeui、Lara K. Leister、Joel A. Cassel、Robert N. DeHaven、Christopher J. LaBuda、Michael Koblish、Patrick J. Little、Bernice L. Brogdon、Steven A. Smith、Roland E. Dolle

  DOI：10.1016/j.bmcl.2009.10.062

  日期：2010.1

  A lead optimization campaign in our previously reported sulfamoyl benzamide class of CB2 agonists was conducted to improve the in vitro metabolic stability pro. le in this series while retaining high potency and selectivity for the CB2 receptor. From this study, compound 14, N-(3,4-dimethyl-5-(morpholinosulfonyl)phenyl)-2,2-dimethylbutanamide, was identified as a potent and selective CB2 agonist exhibiting moderate in vitro metabolic stability and oral bioavailability. Compound 14 demonstrated in vivo efficacy in a rat model of post-surgical pain. (C) 2009 Elsevier Ltd. All rights reserved.
• New Sterically Driven Mode for Generation of Helical Chirality
  作者：Hisanori Ueki、Vadim A. Soloshonok

  DOI：10.1021/ol900357d

  日期：2009.4.16

  The presented results and the available literature data convincingly suggest that there is a new sterically driven mechanism for the formation of supramolecular helicity in the solid state. This mechanism requires the presence of sterically bulky groups, such as tert-butyl, for which the spiral arrangement in uninterrupted hydrogen-bonding chains, serving as an axis for helical structure and maximizing the repulsive stereochemical interactions, provide for the most efficient, spatially economical accommodation of these groups in a crystallographic unit cell.