(5-methyl-2-phenyl-oxazol-4-yl)acetaldehyde | 501031-61-4

• 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-methyl-2-phenyl-oxazol-4-yl)acetaldehyde
• 英文别名: 2-(5-methyl-2-phenyloxazol-4-yl)acetaldehyde；2-(5-Methyl-2-phenyl-oxazol-4-yl)acetaldehyde；2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)acetaldehyde
• CAS: 501031-61-4
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: OILCAWGLITYJMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-methyl-2-phenyl-oxazol-4-yl)acetaldehyde 在 正丁基锂 、 lithium hydroxide monohydrate 、 platinum(IV) oxide trihydrate 、 偶氮二甲酸二异丙酯 、 乙基溴化镁 、 potassium tert-butylate 、 氢气 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 32.34h， 生成 (S)-methyl 2-(4-chlorophenoxy)-3-(2-(3-(5-methyl-2-phenyloxazol-4-yl)propyl)benzo[d]oxazol-5-yl)propanoate
  参考文献：
  名称：

  Design, synthesis and antimicrobial activity of chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives

  摘要：

  Chiral 2-(substituted-hydroxyl)-3-(benzo[d]oxazol-5-yl)propanoic acid derivatives were synthesized and their antibacterial activities were evaluated against fungus, Gram-negative and Gram-positive bacteria. In general, these compounds showed in vitro activities against all screened Gram-negative and Gram-positive bacteria, but poor MIC values for fungus Candida albicans. Remarkably, the (S)-configuration-substituted phenoxyl side chain on position 2 of propanoic acid exerted excellent antibacterial activity against all screened bacteria. Preliminary structure activity studies revealed that the hydrophobic substitutes, para-tert-butyl (11r), para-phenyl (11s) and para-benzyloxy (11t) on the phenoxyl side chain displayed best activities against all Gram-negative and Gram-positive bacteria with MIC values between 1.56 and 6.25 mu g/mL. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.028
• 作为产物：
  描述：

  2-(5-甲基-2-苯基-1,3-恶唑-4-基)-1-乙醇 以 二氯甲烷 为溶剂， 生成 (5-methyl-2-phenyl-oxazol-4-yl)acetaldehyde
  参考文献：
  名称：

  Antidiabetic agents

  摘要：

  本发明提供了式(I)的化合物： 1 其中A、X、Q、Y、B、D、Z和E具有规范中定义的任何值，以及药用可接受的盐，这些化合物作为抗糖尿病药是有用的。还公开了包含一个或多个式I化合物的药物组合物，制备式I化合物的方法，以及用于制备式I化合物的中间体。

  公开号：

  US20030171377A1

文献信息

• Allyl Alcohol as an Acrolein Equivalent in Enantioselective C–C Coupling: Total Synthesis of Amphidinolides R, J, and S
  作者：Cole C. Meyer、Katherine L. Verboom、Madeline M. Evarts、Woo-Ok Jung、Michael J. Krische

  DOI：10.1021/jacs.3c01809

  日期：——

  The first systematic study of catalytic enantioselective 1,2-additions to acrolein is described. Specifically, using allyl alcohol as a tractable, inexpensive acrolein proelectrophile, iridium-catalyzed acrolein allylation is achieved with high levels of regio-, anti-diastereo-, and enantioselectivity. This process delivers 3-hydroxy-1,5-hexadienes, a useful compound class that is otherwise challenging

  描述了丙烯醛催化对映选择性 1,2-加成的首次系统研究。具体而言，使用烯丙醇作为易于处理的、廉价的丙烯醛亲电子试剂，实现了铱催化的丙烯醛烯丙基化，具有高水平的区域选择性、反非对映选择性和对映选择性。该过程产生 3-羟基-1,5-己二烯，这是一种有用的化合物类别，否则很难通过对映选择性催化获得。该方法的两次使用解锁了两栖内酯 R（9 vs 23 步骤，LLS）和两栖内酯 J（9 vs 23 或 26 步骤，LLS）的简明全合成，其制备步骤少于以前可能的一半，并且首次全合成 amphidinolide S（10 步，LLS）。
• Oral antidiabetic agents
  申请人：Warner-Lambert Company LLC

  公开号：EP1577305A1

  公开（公告）日：2005-09-21

  The present invention provides compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein:    A is    X is CH2-CH2-O or -CH2CH2CH2-;    Q is    Y is CH2;    Z is absent;    B is H;    D is H, and E is CO2H; that are useful as antidiabetic agents. Also disclosed are pharmaceutical compositions comprising compounds of formula (I).

  本发明提供了式 (I) 的化合物 或其药学上可接受的盐，其中 A 是 X是CH2- -O或- -； Q 是 Y 是 Z 不存在； B 是 H； D 是 H、 和 E 是 CO2H； 可用作抗糖尿病药物。还公开了包含式（I）化合物的药物组合物。
• Effects of modifications of the linker in a series of phenylpropanoic acid derivatives: Synthesis, evaluation as PPARα/γ dual agonists, and X-ray crystallographic studies
  作者：Agustin Casimiro-Garcia、Christopher F. Bigge、Jo Ann Davis、Teresa Padalino、James Pulaski、Jeffrey F. Ohren、Patrick McConnell、Christopher D. Kane、Lori J. Royer、Kimberly A. Stevens、Bruce J. Auerbach、Wendy T. Collard、Christine McGregor、Stephen A. Fakhoury、Robert P. Schaum、Hairong Zhou

  DOI：10.1016/j.bmc.2008.03.043

  日期：2008.5

  A new series of alpha-aryl or alpha-heteroarylphenyl propanoic acid derivatives was synthesized that incorporate acetylene-, ethylene-, propyl-, or nitrogen-derived linkers as a replacement of the commonly used ether moiety that joins the central phenyl ring with the lipophilic tail. The effect of these modi. cations in the binding and activation of PPAR alpha and PPAR gamma was first evaluated in vitro. Compounds possessing suitable profiles were then evaluated in the ob/ob mouse model of type 2 diabetes. The propylene derivative 40 and the propyl derivative 53 demonstrated robust plasma glucose lowering activity in this model. Compound 53 was also evaluated in male Zucker diabetic fatty rats and was found to achieve normalization of glucose, triglycerides, and insulin levels. An X-ray crystal structure of the complex of 53 with the PPAR gamma-ligand-binding domain was obtained and discussed in this report. (c) 2008 Elsevier Ltd. All rights reserved.
• ORAL ANTIDIABETIC AGENTS
  申请人：Warner-Lambert Company LLC

  公开号：EP1423363A1

  公开（公告）日：2004-06-02
• [EN] ORAL ANTIDIABETIC AGENTS<br/>[FR] AGENTS ANTIDIABETIQUES ORAUX
  申请人：WARNER LAMBERT CO

  公开号：WO2003018553A1

  公开（公告）日：2003-03-06

  The present invention provides compounds of Formula (I): f I wherein A, X, Q, Y, B, D, Z, and E have any of the values defined in the specification, and pharmaceutically acceptable salt thereof, that are useful as antidiabetic agents. Also disclosed are pharmaceutical compositions comprising one or more compounds of Formula I, process for preparing compounds of Formula I, and intermediates useful for preparing compounds of Formula I.