2-(4-乙基氨基-苯基)-1,1,1,3,3,3-六氟-2-丙醇 | 65797-85-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-(4-乙基氨基-苯基)-1,1,1,3,3,3-六氟-2-丙醇
• 英文名称: 2-(4-(ethylamino)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol
• 英文别名: N-ethyl-4-(α-hydroxyhexafluoroisopropyl)aniline；2-(4-Ethylamino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol；2-[4-(ethylamino)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol
• CAS: 65797-85-5
• 化学式: C₁₁H₁₁F₆NO
• 分子量: 287.205
• InChiKey: USWYBKLKNAFHAX-UHFFFAOYSA-N

物化性质

• 熔点：
  93-94 °C(Solv: hexane (110-54-3))
• 沸点：
  308.6±42.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  2-(4-乙基氨基-苯基)-1,1,1,3,3,3-六氟-2-丙醇 在 N-氯代丁二酰亚胺 作用下， 以 丙醇 为溶剂， 生成 2-{3-chloro-4-[ethyl-(thiazol-4-ylmethyl)-amino]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol
  参考文献：
  名称：

  Synthesis and evaluation of anilinohexafluoroisopropanols as activators/modulators of LXRα and β

  摘要：

  A series of branched and unbranched anilinohexafluoroisopropanols related to the known sulfonamide T0901317 were prepared and evaluated as activators/modulators of both LXR alpha and LXR beta. A structure-activity relationship was established and compounds with high potency on both the receptors were identified. Many compounds showed a tendency toward selectivity for LXR beta versus LXR alpha. Several analogues were evaluated for effects on plasma lipoprotein levels in mice. A few of these significantly raised HDL-cholesterol levels in plasma but showed markedly different effects on liver triglyceride content, suggesting that this series may yield candidates with improved efficacy/safety profiles compared to existing molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.081
• 作为产物：
  描述：

  2-(4-氨基苯)-1,1,1,3,3,3-六氟-2-丙醇 在 吡啶 、 硼烷四氢呋喃络合物 作用下， 生成 2-(4-乙基氨基-苯基)-1,1,1,3,3,3-六氟-2-丙醇
  参考文献：
  名称：

  Synthesis and evaluation of anilinohexafluoroisopropanols as activators/modulators of LXRα and β

  摘要：

  A series of branched and unbranched anilinohexafluoroisopropanols related to the known sulfonamide T0901317 were prepared and evaluated as activators/modulators of both LXR alpha and LXR beta. A structure-activity relationship was established and compounds with high potency on both the receptors were identified. Many compounds showed a tendency toward selectivity for LXR beta versus LXR alpha. Several analogues were evaluated for effects on plasma lipoprotein levels in mice. A few of these significantly raised HDL-cholesterol levels in plasma but showed markedly different effects on liver triglyceride content, suggesting that this series may yield candidates with improved efficacy/safety profiles compared to existing molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.081

文献信息

• Cobalt-Catalyzed Selective Functionalization of Aniline Derivatives with Hexafluoroisopropanol
  作者：He Zhao、Shuo Zhao、Xiu Li、Yinyue Deng、Huanfeng Jiang、Min Zhang

  DOI：10.1021/acs.orglett.8b03666

  日期：2019.1.4

  A cobalt-catalyzed site-selective functionalization of aniline derivatives with hexafluoroisopropanol, which enables the synthesis of a wide array of fluoroalkylated anilines, a class of highly valuable building blocks for further preparation of fluorinated functional products, is reported. The developed transformation proceeds with operational simplicity, use of earth-abundant metal catalyst, broad

  报道了用六氟异丙醇对苯胺衍生物进行钴催化的位点选择性官能化，这使得能够合成各种各样的氟代烷基化苯胺，这是一类非常有价值的用于进一步制备氟化功能产物的结构单元。所开发的转化过程将以操作简便，使用富含地球的金属催化剂，广泛的底物范围，良好的官能团耐受性和温和的反应条件进行。
• Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US04218448A1

  公开（公告）日：1980-08-19

  Polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils, such as 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-6-methy l-4H-pyrrolo-[3,2,1-ij]quinolin-7-one, useful as antihypertensive agents.

  多氟羟基异丙基双环和三环碳基吲哚啉类化合物，例如1,2-二氢-8-[2,2,2-三氟-1-羟基-1-(三氟甲基)乙基]-6-甲基-4H-吡咯-[3,2,1-ij]喹啉-7-酮，可用作降压药物。
• Copper(II)‐Catalysed Aerobic Oxidative Coupling of Arylamines with Hexafluoroisopropanol: An Alternative Methodology for Constructing Fluorinated Compounds
  作者：Liangying Wu、Yang Song、Zhanchong Li、Jiabao Guo、Xiaoquan Yao

  DOI：10.1002/adsc.202001048

  日期：2021.1.5

  The selective functionalisation of arylamine derivatives with hexafluoroisopropanol through copper(II)‐catalysed aerobic oxidative coupling was developed to generate various fluoroalkylated arylamines under mild conditions. This method has a wide substrate scope with excellent functional group tolerance and provides the fluorinated products in good to excellent yields. Furthermore, preliminary studies

  开发了在铜（II）催化的需氧氧化偶联作用下，六氟异丙醇对芳胺衍生物的选择性官能化反应，可在温和条件下生成各种氟代烷基化芳基胺。该方法具有广泛的底物范围，具有优异的官能团耐受性，并且以良好至优异的产率提供了氟化产物。此外，初步研究表明该反应是通过自由基机理发生的。该协议使用大气中的O 2作为氧化剂，为构建氟化化合物提供了另一种绿色途径。
• Synthesis and Structure−Activity Relationship of Small-Molecule Malonyl Coenzyme A Decarboxylase Inhibitors
  作者：Jie-Fei Cheng、Mi Chen、David Wallace、Souvothy Tith、Masayuki Haramura、Bin Liu、Chi Ching Mak、Thomas Arrhenius、Sean Reily、Steven Brown、Vicki Thorn、Charles Harmon、Rick Barr、Jason R. B. Dyck、Gary D. Lopaschuk、Alex M. Nadzan

  DOI：10.1021/jm050109n

  日期：2006.3.1

  discovery and structure-activity relationship of first-generation small-molecule malonyl-CoA decarboxylase (MCD; CoA = coenzyme A) inhibitors are reported. We demonstrated that MCD inhibitors increased malonyl-CoA concentration in the isolated working rat hearts. Malonyl-CoA is a potent, endogenous, and allosteric inhibitor of carnitine palmitoyltransferase-I (CPT-I), a key enzyme for mitochondrial fatty acid

  报道了第一代小分子丙二酰辅酶A脱羧酶（MCD； CoA =辅酶A）抑制剂的发现及其与构效关系。我们证明了MCD抑制剂增加了离体大鼠心脏中丙二酰辅酶A的浓度。丙二酰辅酶A是一种有效的，内源性的，变构的肉碱棕榈酰转移酶-I（CPT-1）抑制剂，CPT-1是线粒体脂肪酸氧化的关键酶。由于丙二酰辅酶A水平的增加，脂肪酸氧化速率降低并且葡萄糖氧化速率显着提高。证明5-（N-（4-（1,1,1,3,3,3-六氟-2-羟基丙烷-2-基）苯基）吗啉-4-羧氨基ido）戊酸甲酯（6u）的体内功效）在猪缺血模型中表明MCD抑制剂可能对治疗缺血性心脏病有用。
• Novel hexafluoroisopropanol derivatives
  申请人：Dehmlow Henrietta

  公开号：US20060004068A1

  公开（公告）日：2006-01-05

  The invention is concerned with novel hexafluoroisopropanol derivatives of formula (I) wherein R 1 to R 6 , m and n are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds bind to LXR alpha and LXR beta and can be used as medicaments.

  这项发明涉及式(I)的新型六氟异丙醇衍生物，其中R1至R6，m和n如描述和索赔中所定义，以及其生理上可接受的盐和酯。这些化合物结合到LXR alpha和LXR beta，并可用作药物。