5-chloromethyl-4-methyl-2-(4-trifluoromethylphenyl)-oxazole | 317318-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-chloromethyl-4-methyl-2-(4-trifluoromethylphenyl)-oxazole
• 英文别名: 5-Chloromethyl-4-methyl-2-(4-trifluoromethylphenyl)oxazole；5-(chloromethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazole
• CAS: 317318-99-3
• 化学式: C₁₂H₉ClF₃NO
• 分子量: 275.658
• InChiKey: NTFAPBUAKJQHBK-UHFFFAOYSA-N

物化性质

• 沸点：
  338.7±52.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-chloromethyl-4-methyl-2-(4-trifluoromethylphenyl)-oxazole 在 lithium hydroxide 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 16.0h， 生成 4-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-ylmethoxy]-benzoic acid
  参考文献：
  名称：

  Novel selective small molecule agonists for peroxisome proliferator-activated receptor δ (PPARδ)—synthesis and biological activity

  摘要：

  We report the synthesis and biological activity of a new series of small molecule agonists of the human Peroxisome Proliferator-Activated Receptor delta (PPARdelta). Several hits were identified from our original libraries containing lipophilic carboxylic acids. Optimization of these hits by structure-guided design led to 7k (GW501516) and 71 (GW0742), which shows an EC50 Of 1.1 nM against PPARdelta with 1000-fold selectivity over the other human subtypes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00207-5
• 作为产物：
  描述：

  4-三氟甲基苯甲酸 在 氯化亚砜 、 ammonium acetate 、 potassium carbonate 、 溶剂黄146 、 红铝 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 5-chloromethyl-4-methyl-2-(4-trifluoromethylphenyl)-oxazole
  参考文献：
  名称：

  A New Approach to the Synthesis of 2-Aryl-4-halomethyl-5-methyl-1,3-oxa­zoles by Highly Regioselective Direct Halogenation with NBS or NCS/MeCN

  摘要：

  描述了一种简单高效的合成2-芳基-4-溴甲基-5-甲基-1,3-噁唑2和2-芳基-4-氯甲基-5-甲基-1,3-噁唑3的方法。在温和条件下，2-芳基-4,5-二甲基-1,3-噁唑1与N-溴代琥珀酰亚胺和N-氯代琥珀酰亚胺在乙腈中反应，以中等至良好的收率提供了具有极高区域选择性的4-卤甲基异构体。

  DOI：

  10.1055/s-2004-834862

文献信息

• Aniline derivatives, their manufacture and use as pharmaceuticals
  申请人：——

  公开号：US20040248951A1

  公开（公告）日：2004-12-09

  This invention relates to compounds of the formula 1 wherein X is N and Y is S or O; or X is S or O and Y is N; R 1 is hydrogen or C 1-7 -alkyl; R 2 and R 3 independently from each other are selected from the group consisting of hydrogen, C 1-7 -alkyl and C 1-7 -alkoxy; R 4 , R 5 , R 6 , and R 7 independently from each other are selected from the group consisting of hydrogen, C 1-7 -alkyl, C 3-7 -cycloalkyl, halogen, C 1-7 -alkoxy, C 1-7 -alkyl-C 1-7 -alkoxy-C 1-7 -alkyl, C 2-7 -alkenyl, C 2-7 -alkinyl, fluoro-C 1-7 -alkyl and cyano; R 8 is selected from the group consisting of hydrogen, C 1-7 -alkyl, C 3-7 -cycloalkyl and fluoro-C 1-7 -alkyl; R 9 is selected from the group consisting of hydrogen, C 1-7 -alkyl, C 2-7 -alkinyl, C 3-7 -cycloalkyl and fluoro-C 1-7 -alkyl; R 10 is selected from the group consisting of hydrogen, C 1-7 -alkyl, C 2-7 -alkinyl, C 3-7 -cycloalkyl and fluoro-C 1-7 -alkyl; R 11 is aryl or heteroaryl; N is 0, 1 or 2; and all enantiomers and pharmaceutically acceptable salts and/or esters thereof and their use as PPAR activators.

  这项发明涉及以下式的化合物 1 其中 X为N，Y为S或O；或 X为S或O，Y为N； R 1 为氢或C 1-7 -烷基； R 2 和R 3 彼此独立地从氢、C 1-7 -烷基和C 1-7 -烷氧基组成的群中选择； R 4 、R 5 、R 6 和R 7 彼此独立地从氢、C 1-7 -烷基、C 3-7 -环烷基、卤素、C 1-7 -烷氧基、C 1-7 -烷基-C 1-7 -烷氧基-C 1-7 -烷基、C 2-7 -烯基、C 2-7 -炔基、氟代C 1-7 -烷基和氰基中选择； R 8 从氢、C 1-7 -烷基、C 3-7 -环烷基和氟代C 1-7 -烷基中选择； R 9 从氢、C 1-7 -烷基、C 2-7 -炔基、C 3-7 -环烷基和氟代C 1-7 -烷基中选择； R 10 从氢、C 1-7 -烷基、C 2-7 -炔基、C 3-7 -环烷基和氟代C 1-7 -烷基中选择； R 11 为芳基或杂环芳基； N为0、1或2； 以及所有对映体和药学上可接受的盐和/或酯以及它们作为PPAR激动剂的用途。
• Indolyl derivatives as liver-X-receptor (LXR) modulators
  申请人：Dehmlow Henrietta

  公开号：US20050245515A1

  公开（公告）日：2005-11-03

  The invention relates to compounds of formula (I): and pharmaceutically acceptable salts and pharmaceutically acceptable esters thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A, m, n and p are defined as in claim 1. These compounds can be used as pharmaceutical compositions for the treatment of, for example, diabetes.

  这项发明涉及式(I)的化合物： 以及其药学上可接受的盐和药学上可接受的酯，其中R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，R 6 ，A，m，n和p的定义如权利要求书中所述。 这些化合物可用作治疗糖尿病等疾病的药物组合物。
• [EN] SULFAMIDE DERIVATIVES AND PHARMACEUTICAL COMPOSITION FOR UPREGULATION OF LIPID METABOLISM COMPRISING SAME<br/>[FR] DERIVES DE SULFAMIDE ET COMPOSITION PHARMACEUTIQUE SERVANT A REGULER POSITIVEMENT LE METABOLISME DES LIPIDES ET CONTENANT CES DERIVES
  申请人：CRYSTALGENOMICS INC

  公开号：WO2006006832A1

  公开（公告）日：2006-01-19

  The present invention relates to a novel sulfamide derivative, a pharmaceutically acceptable salt thereof and a pharmaceutical composition for upregulation of lipid metabolism comprising same as an active ingredient.

  本发明涉及一种新型磺胺酰胺衍生物，其药用可接受的盐以及一种含有其作为活性成分的用于上调脂质代谢的制药组合物。
• A Highly Regioselective Preparation of 4-Chloromethyl-5-methyl-2-aryl-1,3-oxazoles
  作者：George?T. Lee、Xinglong Jiang、T.?R. Vedananda、Kapa Prasad、Oljan Repi?

  DOI：10.1002/adsc.200404135

  日期：2004.10

  A facile highly regioselective process is described for the formation of 4-chloromethyl-1,3-oxazoles from 1,3-oxazole N-oxide/HCl salts. An explanation is presented for the high regioselectivity in deoxygenation-chlorination using POCl3 with HCl salts compared to the corresponding free N-oxides. The method is quite general and the products are isolated by direct precipitation in all cases studied.

  描述了一种由1，3-恶唑N-氧化物/ HCl盐形成4-氯甲基-1，3-恶唑的简便的高度区域选择性方法。与相应的游离N-氧化物相比，使用POCl 3与HCl盐进行的脱氧-氯化反应具有很高的区域选择性。该方法非常通用，并且在所有研究的情况下均通过直接沉淀法分离出产物。
• Peroxisome proliferator activated receptor modulators
  申请人：Conner Eugene Scott

  公开号：US20060084663A1

  公开（公告）日：2006-04-20

  The present invention is directed to compounds represented by the following structural formula, and pharmaceutically acceptable salts thereof, Formula I: wherein: (a) R5 is selected from the group consisting of (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkenyl, substituted aryl(C 0 -C 4 )alkyl, substituted aryloxy(C 0 -C 4 )alkyl, substituted arylthio(C 0 -C 4 )alkyl, unsubstituted aryl(C 0 -C 4 )alkyl, unsubstituted aryloxy(C 0 -C 4 )alkyl, and unsubstituted arylthio(C 0 -C 4 )alkyl; (b) T1 is C or N; (c) Q is selected from the group consisting of O, a single bond, O(CH 2 ) q and C; (d) q is 1 or 2; (e) W is selected from the group consisting of O, S, (CH 2 ) r N(R20)(CH 2 ) k , NHSO 2 , C(O)N(R20)(CH 2 ) r , (CH 2 ) r N(R20)C(O), and SO 2 ; (f) X is C m H 2m ; (g) m is 0, 1 or 2; (h) A is an functional group selected from the group consisting of carboxyl, C1-C3 alkylnitrile, carboxamide, and (CH 2 ) n COOR19; and (i) R19 is selected from the group consisting of hydrogen, optionally substituted C1-C4alkyl and optionally substituted arylmethyl.

  本发明涉及以下结构式所表示的化合物及其药学上可接受的盐，式I：其中：(a) R5选自(C1-C6)烷基，(C1-C6)烯基，取代芳基(C0-C4)烷基，取代芳氧基(C0-C4)烷基，取代芳硫基(C0-C4)烷基，未取代芳基(C0-C4)烷基，未取代芳氧基(C0-C4)烷基和未取代芳硫基(C0-C4)烷基组成的群体；(b) T1为C或N；(c) Q选自O，单键，O(CH2)q和C的群体；(d) q为1或2；(e) W选自O，S，(CH2)rN(R20)(CH2)k，NHSO2，C(O)N(R20)(CH2)r，(CH2)rN(R20)C(O)和SO2的群体；(f) X为CmH2m；(g) m为0，1或2；(h) A为从羧基，C1-C3烷基腈，羧酰胺和(CH2)nCOOR19的群体中选取的一个功能基团；(i) R19选自氢，可选取代的C1-C4烷基和可选取代的芳基甲基的群体。