4,4,4-trifluoro-1-(4-(trifluoromethyl)phenyl)propan-1-ol | 514843-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4,4-trifluoro-1-(4-(trifluoromethyl)phenyl)propan-1-ol
• 英文别名: 4,4,4-Trifluoro-1-[4-(trifluoromethyl)phenyl]butan-1-ol
• CAS: 514843-72-2
• 化学式: C₁₁H₁₀F₆O
• 分子量: 272.19
• InChiKey: HIRJNQCBGPJFPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 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：
  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-1-(4-(trifluoromethyl)phenyl)propan-1-ol 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (S)-3-Methyl-4-[(S)-4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butyl]-piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Piperazine-Based CCR5 Antagonists as HIV-1 Inhibitors. IV. Discovery of 1-[(4,6-Dimethyl-5-pyrimidinyl)carbonyl]- 4-[4-{2-methoxy-1(R)-4-(trifluoromethyl)phenyl}ethyl-3(S)-methyl-1-piperazinyl]- 4-methylpiperidine (Sch-417690/Sch-D), a Potent, Highly Selective, and Orally Bioavailable CCR5 Antagonist

  摘要：

  The nature and the size of the benzylic substituent are shown to be the key to controlling receptor selectivity (CCR5 vs M1, M2) and potency in the title compounds. Optimization of the lead benzylic methyl compound 3 led to the methoxymethyl analogue 30, which had excellent receptor selectivity and oral bioavailability in rats and monkeys. Compound 30 (Sch-417690/Sch-D), a potent inhibitor of HIV-1 entry into target cells, is currently in clinical trials.

  DOI：

  10.1021/jm0304515
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 1-碘-3,3,3-三氟丙烷 在 碘 magnesium 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 4,4,4-trifluoro-1-(4-(trifluoromethyl)phenyl)propan-1-ol
  参考文献：
  名称：

  17-Beta hydroxysteroid dehydrogenase type 3 inhibitors for the treatment of androgen dependent diseases

  摘要：

  揭示了以下式(I)的化合物：1的前药，或者化合物或前药的药用可接受盐，这些化合物对于抑制第3型17β-羟基类固醇脱氢酶是有用的。还揭示了含有这些化合物的药物组合物，以及它们用于治疗或预防雄激素依赖性疾病的用途。

  公开号：

  US20030232837A1

文献信息

• Selective Hydrogen Atom Abstraction through Induced Bond Polarization: Direct α‐Arylation of Alcohols through Photoredox, HAT, and Nickel Catalysis
  作者：Jack Twilton、Melodie Christensen、Daniel A. DiRocco、Rebecca T. Ruck、Ian W. Davies、David W. C. MacMillan

  DOI：10.1002/anie.201800749

  日期：2018.5.4

  The combination of nickel metallaphotoredox catalysis, hydrogen atom transfer catalysis, and a Lewis acid activation mode, has led to the development of an arylation method for the selective functionalization of alcohol α‐hydroxy C−H bonds. This approach employs zinc‐mediated alcohol deprotonation to activate α‐hydroxy C−H bonds while simultaneously suppressing C−O bond formation by inhibiting the

  镍金属光氧化还原催化、氢原子转移催化和路易斯酸活化模式的结合，开发了一种用于醇α-羟基C-H键选择性官能化的芳基化方法。该方法采用锌介导的醇去质子化来激活 α-羟基 C-H 键，同时通过抑制醇镍物质的形成来抑制 C-O 键的形成。使用锌基路易斯酸也会使其他氢键失活，例如 α-氨基和 α-氧基 C-H 键。这种方法有助于快速获得苯甲醇，这是药物发现的一个重要主题。药物百忧解的三步合成例证了这种新方法的实用性。
• PIPERIDINE- AND PIPERAZINEACETAMIDES AS 17BETA HYDROXYSTEROID DEHYDROGENASE TYPE 3 INHIBITORS FOR THE TREATMENT OF ANDROGEN DEPENDENT DISEASES
  申请人：Schering Corporation

  公开号：EP1436281B1

  公开（公告）日：2010-06-16
• Piperazine-Based CCR5 Antagonists as HIV-1 Inhibitors. IV. Discovery of 1-[(4,6-Dimethyl-5-pyrimidinyl)carbonyl]- 4-[4-{2-methoxy-1(<i>R</i>)-4-(trifluoromethyl)phenyl}ethyl-3(<i>S</i>)-methyl-1-piperazinyl]- 4-methylpiperidine (Sch-417690/Sch-D), a Potent, Highly Selective, and Orally Bioavailable CCR5 Antagonist
  作者：Jayaram R. Tagat、Stuart W. McCombie、Dennis Nazareno、Marc A. Labroli、Yushi Xiao、Ruo W. Steensma、Julie M. Strizki、Bahige M. Baroudy、Kathleen Cox、Jean Lachowicz、Geoffrey Varty、Robert Watkins

  DOI：10.1021/jm0304515

  日期：2004.5.1

  The nature and the size of the benzylic substituent are shown to be the key to controlling receptor selectivity (CCR5 vs M1, M2) and potency in the title compounds. Optimization of the lead benzylic methyl compound 3 led to the methoxymethyl analogue 30, which had excellent receptor selectivity and oral bioavailability in rats and monkeys. Compound 30 (Sch-417690/Sch-D), a potent inhibitor of HIV-1 entry into target cells, is currently in clinical trials.
• 17-Beta hydroxysteroid dehydrogenase type 3 inhibitors for the treatment of androgen dependent diseases
  申请人：Schering Corporation

  公开号：US20030232837A1

  公开（公告）日：2003-12-18

  There are disclosed compounds of the formula (I): 1 prodrugs thereof, or pharmaceutically acceptable salts of the compounds or of said prodrugs which are useful as inhibitors of Type 3 17&bgr;-Hydroxysteroid Dehydrogenase. Also disclosed are pharmaceutical compositions containing said compounds and their use for the treatment or prevention of androgen dependent diseases.

  揭示了以下式(I)的化合物：1的前药，或者化合物或前药的药用可接受盐，这些化合物对于抑制第3型17β-羟基类固醇脱氢酶是有用的。还揭示了含有这些化合物的药物组合物，以及它们用于治疗或预防雄激素依赖性疾病的用途。