methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazoline-4-carboxylate | 1055051-35-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazoline-4-carboxylate
• 英文别名: methyl 2-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 1055051-35-8
• 化学式: C₁₂H₁₀F₃NO₃
• 分子量: 273.212
• InChiKey: RQDYZAGLOUDTFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazoline-4-carboxylate 在 silver(I) acetate 、 copper diacetate 、 palladium diacetate 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl 2-(p-trifluoromethylphenyl)-5-phenyloxazole-4-carboxylate
  参考文献：
  名称：

  Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C–H bond cleavage

  摘要：

  首次实现了通过双C–H键断裂的铂催化直接C5-芳基化反应，将简单的未活化芳烃与azole-4-羧酸酯进行反应。该协议提供了一种简便的方法，获得了多种5-芳基取代的azole-4-羧酸衍生物，并具有良好的功能团耐受性。

  DOI：

  10.1039/c2cc00081d
• 作为产物：
  描述：

  对三氟甲基苯腈 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-[4-(trifluoromethyl)phenyl]-1,3-oxazoline-4-carboxylate
  参考文献：
  名称：

  Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C–H bond cleavage

  摘要：

  首次实现了通过双C–H键断裂的铂催化直接C5-芳基化反应，将简单的未活化芳烃与azole-4-羧酸酯进行反应。该协议提供了一种简便的方法，获得了多种5-芳基取代的azole-4-羧酸衍生物，并具有良好的功能团耐受性。

  DOI：

  10.1039/c2cc00081d

文献信息

• Substituted heterocyclic compounds
  申请人：——

  公开号：US20030176447A1

  公开（公告）日：2003-09-18

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes, and for increasing HDL plasma levels in mammals.

  揭示了一种新颖的杂环衍生物，用于治疗各种疾病状态，特别是心血管疾病，如心房和心室心律失常、间歇性跛行、普林兹梅塔（变异）心绞痛、稳定和不稳定心绞痛、运动诱发性心绞痛、充血性心力衰竭和心肌梗死。这些化合物还可用于治疗糖尿病，并可增加哺乳动物的高密度脂蛋白血浆水平。
• Stereodivergent Synthesis of α-Quaternary Serine and Cysteine Derivatives Containing Two Contiguous Stereogenic Centers via Synergistic Cu/Ir Catalysis
  作者：Hui-Min Wu、Zongpeng Zhang、Fan Xiao、Liang Wei、Xiu-Qin Dong、Chun-Jiang Wang

  DOI：10.1021/acs.orglett.0c01687

  日期：2020.6.19

  A stereodivergent preparation of α-quaternary serine/cysteine derivatives incorporating two adjacent stereogenic centers has been developed through Cu/Ir-catalyzed asymmetric allylation of 2-oxazoline-4-carboxylates and 2-thiazoline-4-carboxylates. Tuning the electronic effect is the key to enhancing the reactivity of 2-oxazoline-4-carboxylates and suppressing the undesired β-elimination. The salient

  通过Cu / Ir催化2-恶唑啉-4-羧酸盐和2-噻唑啉-4-羧酸盐的不对称烯丙基化反应，开发了包含两个相邻的立体生成中心的α-季丝氨酸/半胱氨酸衍生物的立体发散剂。调节电子效应是增强2-恶唑啉-4-羧酸盐的反应性并抑制不希望的β-消除的关键。该方案的显着特征是，可以通过两种不同手性催化剂的成对组合，从相同的起始原料中获得α-季丝氨酸和半胱氨酸衍生物的所有四个立体异构体。
• CATALYST FOR ASYMMETRIC HYDROGENATION OF COMPOUND CONTAINING CARBON DOUBLE BOND
  申请人：GLACEUM INC.

  公开号：US20210395282A1

  公开（公告）日：2021-12-23

  The present invention may provide an asymmetric hydrogenation catalyst capable of resolving enantiomers with excellent enantioselectivity from a carbon-carbon double bond-containing compound. The catalyst according to one embodiment of the present invention includes: an iridium cation; and a ligand bonded to the iridium cation.

  本发明可能提供一种不对称加氢催化剂，能够从含有碳-碳双键的化合物中以优异的对映选择性分离对映体。根据本发明的一种实施例，所述催化剂包括：铱阳离子；以及与铱阳离子结合的配体。
• Environmental-benign oxidation of 2-oxazolines to oxazoles by dioxygen as the sole oxidant
  作者：Yue Huang、Lijun Ni、Haifeng Gan、Yu He、Jinyi Xu、Xiaoming Wu、Hequan Yao

  DOI：10.1016/j.tet.2011.01.050

  日期：2011.3

  A facile and environment-benign oxidation by dioxygen as the sole oxidant was applied for the conversion of 2-oxazolines to oxazoles. The substituent effect on 2-oxazoline ring was investigated. The use of this methodology for the synthesis of a key intermediate of a CDC25 phosphatase inhibitor (SC-alpha alpha delta 9) as an anticancer agent was also described. (C) 2011 Elsevier Ltd. All rights reserved.
• Copper(II)-catalyzed oxidation of 4-carboxythiazolines and 4-carboxyoxazolines to 4-carboxythiazoles and 4-carboxyoxazoles
  作者：Yiyun Wang、Ziyuan Li、Yue Huang、Changhua Tang、Xiaoming Wu、Jinyi Xu、Hequan Yao

  DOI：10.1016/j.tet.2011.07.016

  日期：2011.9

  A mild copper(II)-catalyzed oxidation of 4-carboxythiazolines and 4-carboxyoxazolines to 4-carboxythiazoles and 4-carboxyoxazoles has been developed. Various substrates with alkyl or aryl substitutions at 2-position on azoline ring could be smoothly oxidized to the desired products in good to excellent yields. Moreover, the hydrolysis of the ester group could be avoided under this method. (C) 2011 Elsevier Ltd. All rights reserved.