4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-butan-1-ol | 769169-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-butan-1-ol
• 英文别名: 4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)butan-1-ol；4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butan-1-ol
• CAS: 769169-73-5
• 化学式: C₆H₈F₆O
• 分子量: 210.119
• InChiKey: AHGLEYAJYLEUHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-butan-1-ol 在 titanium(IV) tetraethanolate 、 硫酸 、 戴斯-马丁氧化剂 、 异丙醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 8.25h， 生成 (2S)-2-amino-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-pentanoic acid
  参考文献：
  名称：

  Asymmetric synthesis of novel α-amino acids with β-branched side chains

  摘要：

  An asymmetric synthesis of alpha-amino acids with novel beta-branched side chains has been implemented. The syntheses feature a p-toluenesulfinylimine induced chiral Strecker approach and were found to be applicable to the introduction of both aliphatic and aromatic P-branched sidechains for preparation of previously unknown alpha-amino acids. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.041
• 作为产物：
  描述：

  4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butyric acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以41%的产率得到4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-butan-1-ol
  参考文献：
  名称：

  Trifluoromethyl-containing phenylsulfonamide beta amyloid inhibitors

  摘要：

  提供了Formula (I)的化合物，或其药用可接受的盐和/或水合物或前药，其中Formula (I)具有以下结构： 在此定义了R1-R7。这些化合物在治疗从阿尔茨海默病、淀粉样血管病、脑淀粉样血管病、全身性淀粉样病、荷兰型遗传性脑出血伴淀粉样病、包涵体肌炎、轻度认知障碍（MCI）和唐氏综合征等疾病的药物中对受试者有用。

  公开号：

  US20070249722A1

文献信息

• Trifluoromethyl-containing phenylsulfonamide beta amyloid inhibitors
  申请人：Porte Alexander Michael

  公开号：US20070249722A1

  公开（公告）日：2007-10-25

  A compound of Formula (I), or pharmaceutically acceptable salts and/or hydrates or prodrugs thereof, wherein Formula (I) has the structure: is provided, wherein R 1 -R 7 are defined herein. These compounds are useful in medicaments for treating a disease selected from the group consisting of Alzheimer's Disease, amyloid angiopathy, cerebral amyloid angiopathy, systemic amyloidosis, hereditary cerebral hemorrhage with amyloidosis of the Dutch type, inclusion body myositis, mild cognitive impairment (MCI) and Down's syndrome, in a subject.

  提供了Formula (I)的化合物，或其药用可接受的盐和/或水合物或前药，其中Formula (I)具有以下结构： 在此定义了R1-R7。这些化合物在治疗从阿尔茨海默病、淀粉样血管病、脑淀粉样血管病、全身性淀粉样病、荷兰型遗传性脑出血伴淀粉样病、包涵体肌炎、轻度认知障碍（MCI）和唐氏综合征等疾病的药物中对受试者有用。
• Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof
  申请人：Wyeth

  公开号：US20040198778A1

  公开（公告）日：2004-10-07

  Compounds of Formula (I), 1 are provided where T is CHO, CON, or C(OH)R 1 R 2 ; R 1 and R 2 are hydrogen, optionally substituted lower alkyl, CF 3 , optionally substituted alkenyl, or optionally substituted alkynyl; R 3 is hydrogen or optionally substituted lower alkyl; R 4 is (CF 3 ) n alkyl, (CF 3 ) n (substitutedalkyl), (CF 3 ) n alkylphenyl, (CF 3 ) n alkyl(substitutedphenyl), or (F) n cycloalkyl; n=1-3; R 5 is hydrogen, halogen, CF 3 , diene fused to Y when Y═C, or substituted diene fused to Y when Y═C; W, Y and Z are C, CR 6 or N where at least one of W, Y or Z are C; R 6 is hydrogen, halogen, or optionally substituted lower alkyl; X is O, S, SO 2 , or NR 7 ; R 7 is hydrogen, optionally substituted lower alkyl, optionally substituted benzyl, or optionally substituted phenyl; and R 8 is lower alkyl, CF 3 , or optionally substituted phenyl. Methods of preparing and using these compounds for inhibiting beta amyloid production and for treatment of Alzheimer's Disease and Down's syndrome are also described.

  提供了具有式(I)的化合物，其中T为CHO、CON或C(OH)R1R2；R1和R2为氢、可选择取代的较低烷基、CF3、可选择取代的烯烃或可选择取代的炔烃；R3为氢或可选择取代的较低烷基；R4为(CF3)n烷基、(CF3)n(取代烷基)、(CF3)n烷基苯基、(CF3)n烷基(取代苯基)或(F)n环烷基；n=1-3；R5为氢、卤素、CF3、与Y融合的双烯烃（当Y为C时）、或与Y融合的取代双烯烃（当Y为C时）；W、Y和Z为C、CR6或N，其中至少有一个为C；R6为氢、卤素或可选择取代的较低烷基；X为O、S、SO2或NR7；R7为氢、可选择取代的较低烷基、可选择取代的苄基或可选择取代的苯基；R8为较低烷基、CF3或可选择取代的苯基。还描述了制备和使用这些化合物来抑制β淀粉样蛋白的产生，以及治疗阿尔茨海默病和唐氏综合征的方法。
• Development of a Novel Class of Glucose Transporter Inhibitors
  作者：Dasheng Wang、Po-Chen Chu、Chia-Ning Yang、Ribai Yan、Yu-Chung Chuang、Samuel K. Kulp、Ching-Shih Chen

  DOI：10.1021/jm300015m

  日期：2012.4.26

  a thiazolidinedione peroxisome proliferator-activated receptor (PPAR)γ agonist, was, in part, attributable to its ability to block glucose uptake independently of PPARγ, we used its PPARγ-inactive analogue to develop a novel class of glucose transporter (GLUT) inhibitors. This lead optimization led to compound 30 5-(4-hydroxy-3-trifluoromethylbenzylidene)-3-[4,4,4-trifluoro-2-methyl-2-(2,2,2-trifl

  根据我们的发现，5-4-[(1-甲基环己基)甲氧基]苄基}噻唑烷-2,4-二酮，一种噻唑烷二酮过氧化物酶体增殖物激活受体 (PPAR)γ 激动剂的抗肿瘤作用，在部分归因于其独立于 PPARγ 阻断葡萄糖摄取的能力，我们使用其 PPARγ 非活性类似物开发了一类新型葡萄糖转运蛋白 (GLUT) 抑制剂。这种先导优化导致化合物30 5-(4-hydroxy-3-trifluoromethylbenzylidene)-3-[4,4,4-trifluoro-2-methyl-2-(2,2,2-trifluoroethyl)butyl]thiazolidine- 2,4-二酮}作为最佳药物，通过抑制葡萄糖摄取表现出高抗肿瘤效力（IC 50, 2.5 μM)，同时对前列腺和乳腺上皮细胞没有细胞毒性。这种葡萄糖摄取抑制与 GLUT1 (IC 50 , 2 μM)的抑制有关。此外，化合物30的抗肿瘤作
• [EN] FLUORO-AND TRIFLUOROALKYL-CONTAINING HETEROCYCLIC SULFONAMIDE INHIBITORS OF BETA AMYLOID PRODUCTION AND DERIVATIVES THEREOF<br/>[FR] SULFONAMIDES HETEROCYCLIQUES CONTENANT DES FLUORO-ET-TRIFLUOROALKYLES, INHIBITEURS DE LA PRODUCTION DE BETA AMYLOIDE, ET LEURS DERIVES
  申请人：WYETH CORP

  公开号：WO2004092155A1

  公开（公告）日：2004-10-28

  Compounds of Formula (I), are provided where T is CHO, COR8, or C(OH)R1R2; R1 and R2 are hydrogen, optionally substituted lower alkyl, CF3, optionally substituted alkenyl, or optionally substituted alkynyl; R3 is hydrogen or optionally substituted lower alkyl; R4 is (CF3)nalkyl, (CF3)n(substitutedalkyl), (CF3)nalkylphenyl, (CF3)nalkyl(substitutedphenyl), or (F)ncycloalkyl; n=1-3; R5 is hydrogen, halogen, CF3, diene fused to Y when Y=C, or substituted diene fused to Y when Y=C; W, Y and Z are C, CR6 or N where at least one of W, Y or Z are C; R6 is hydrogen, halogen, or optionally substituted lower alkyl; X is O, S, SO2, or NR7; R7 is hydrogen, optionally substituted lower alkyl, optionally substituted benzyl, or optionally substituted phenyl; and R8 is lower alkyl, CF3, or optionally substituted phenyl. Methods of preparing and using these compounds for inhibiting beta amyloid production and for treatment of Alzheimer's Disease and Down's syndrome are also described.

  提供了化合物公式(I)，其中T为CHO、COR8或C(OH)R1R2；R1和R2为氢、可选取代的低碳基、CF3、可选取代的烯基或可选取代的炔基；R3为氢或可选取代的低碳基；R4为(CF3)n烷基、(CF3)n(取代烷基)、(CF3)n烷基苯基、(CF3)n烷基(取代苯基)或(F)ncycloalkyl；n=1-3；R5为氢、卤素、CF3、与Y融合的双烯烃（当Y=C时）或取代的与Y融合的双烯烃（当Y=C时）；W、Y和Z为C、CR6或N，其中至少有一个为C；R6为氢、卤素或可选取代的低碳基；X为O、S、SO2或NR7；R7为氢、可选取代的低碳基、可选取代的苯甲基或可选取代的苯基；R8为低碳基、CF3或可选取代的苯基。还描述了制备和使用这些化合物以抑制β淀粉样蛋白的产生以及治疗阿尔茨海默病和唐氏综合症的方法。
• TRIFLUOROMETHYL-CONTAINING PHENYLSULFONAMIDE BETA AMYLOID INHIBITORS
  申请人：Porte Alexander Michael

  公开号：US20090221711A1

  公开（公告）日：2009-09-03

  A compound of Formula (I), or pharmaceutically acceptable salts and/or hydrates or prodrugs thereof, wherein Formula (I) has the structure: is provided, wherein R 1 -R 7 are defined herein. These compounds are useful in medicaments for treating a disease selected from the group consisting of Alzheimer's disease, amyloid angiopathy, cerebral amyloid angiopathy, systemic amyloidosis, hereditary cerebral hemorrhage with amyloidosis of the Dutch type, inclusion body myositis, mild cognitive impairment (MCI) and Down's syndrome, in a subject.

  提供了公式（I）的化合物，或其药学上可接受的盐和/或水合物或前药，其中公式（I）具有结构：其中R1-R7在此定义。这些化合物在治疗以下疾病的药物中有用，所述疾病选自阿尔茨海默病，淀粉样血管病，脑淀粉样血管病，全身性淀粉样变性，荷兰型遗传性脑出血伴有淀粉样沉积，包涵体肌病，轻度认知障碍（MCI）和唐氏综合症。