3-chloro-5-phenyl-2-isoxazoline | 62056-52-4

• 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: 3-chloro-5-phenyl-2-isoxazoline
• 英文别名: 3-chloro-4,5-dihydro-5-phenyl isoxazole；3-chloro-5-phenyl-4,5-dihydroisoxazole；5-phenyl-3-chloroisoxazoline；butyl 3-(trichlorovinyl)-4,5-dihydroisoxazole-5-carboxylate；3-chloro-5-phenyl-4,5-dihydro-1,2-oxazole；Isoxazole, 3-chloro-4,5-dihydro-5-phenyl-
• CAS: 62056-52-4
• 化学式: C₉H₈ClNO
• 分子量: 181.622
• InChiKey: RQKHDLVXQFONPI-UHFFFAOYSA-N

物化性质

• 沸点：
  266.7±43.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-5-phenyl-2-isoxazoline 在 五羰基铁 、 溶剂黄146 作用下， 反应 20.0h， 以81%的产率得到3-羟基-3-苯基丙腈正离子
  参考文献：
  名称：

  Halling, Karen; Thomsen, Ib; Torssell, Kurt B. G., Liebigs Annalen der Chemie, 1989, p. 985 - 990

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴-4,5-二氢-5-苯基异噁唑 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-chloro-5-phenyl-2-isoxazoline
  参考文献：
  名称：

  Discovery of Covalent Inhibitors of Glyceraldehyde-3-phosphate Dehydrogenase, A Target for the Treatment of Malaria

  摘要：

  We developed a new class of covalent inhibitors of Plasmodium falciparum glyceraldehyde-3-phosphate dehydrogenase, a validated target for the treatment of malaria, by screening a small library of 3-bromo-isoxazoline derivatives that inactivate the enzyme through a covalent, selective bond to the catalytic cysteine, as demonstrated by mass spectrometry. Substituents on the isoxazolinic ring modulated the potency up to 20-fold, predominantly due to an electrostatic effect, as assessed by computational analysis.

  DOI：

  10.1021/jm500747h

文献信息

• [EN] ISOXAZOLINES AS INHIBITORS OF FATTY ACID AMIDE HYDROLASE<br/>[FR] ISOXAZOLINES EN TANT QU'INHIBITEURS DE L'HYDROLASE DES AMIDES D'ACIDES GRAS
  申请人：INFINITY PHARMACEUTICALS INC

  公开号：WO2010135360A1

  公开（公告）日：2010-11-25

  The present invention provides isoxazoline FAAH inhibitors of the formula (I): or pharmaceutically acceptable forms thereof, wherein each of G, Ra, Rb, Rc, and Rd are as defined herein. The present invention also provides pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable form thereof, and a pharmaceutically acceptable excipient. The present invention also provides methods for treating an FAAH-mediated condition comprising administering a therapeutically effective amount of a compound of formula (I), or pharmaceutically acceptable form thereof, to a subject in need thereof.

  本发明提供了式(I)的异噁唑啉FAAH抑制剂或其药用可接受形式，其中G、Ra、Rb、Rc和Rd中的每一个如本文所定义。本发明还提供了包括式(I)化合物或其药用可接受形式以及药用可接受赋形剂的药物组合物。本发明还提供了治疗FAAH介导疾病的方法，包括向需要的受试者施用式(I)化合物或其药用可接受形式的治疗有效量。
• Chemistry of Polyhalogenated Nitrobutadienes, Part 7: A Novel Synthetic Access to Chlorinated Nitrile Oxides
  作者：Dieter Kaufmann、Eva Nutz、Viktor Zapol’skii

  DOI：10.1055/s-0029-1216906

  日期：——

  Reaction of gem-dichloronitroalkenes with base leads to the formation of chlorinated nitrile oxides, probably via a cyclic intermediate. The 1,3-dipoles can be trapped with alkenes to give dihydroisoxazoles with a chlorinated side chain in 3-position. This novel synthetic method is fairly general.

  gem-二氯硝基烯与碱反应导致氯化硝基氧化物的形成，可能通过一个环状中间体。1,3-偶极子可以与烯烃反应，从而生成在3位具有氯化侧链的二氢异噁唑。这种新颖的合成方法相当通用。
• Synthesis of analogues of the antitumor antibiotic at-125 (acivicin)
  作者：Robert V. Stevens、Richard P. Polniaszek

  DOI：10.1016/s0040-4020(01)91849-6

  日期：1983.1

  Several haloisoxazoline analogues of α-amino-3-chloro-4,5-dihydro-5-isoxazole acetic acid (1, AT-125) were prepared by means of 1,3-dipolar cycloaddition methodology. The chemistry of these compounds is discussed, and a possible biological mode of action of AT-125 presented.

  借助1，3-偶极环加成法制备了几种α-氨基-3-氯-4，5-二氢-5-异恶唑乙酸的卤代异恶唑啉类似物（1，AT-125）。讨论了这些化合物的化学性质，并提出了AT-125可能的生物学作用方式。
• Thiazolylpiperidine Derivatives as Fungicides
  申请人：CRISTAU Pierre

  公开号：US20110046178A1

  公开（公告）日：2011-02-24

  Thiazolylpiperidine derivatives of the formula (I), in which the symbols A, G, Y, n, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given in the description, and also agrochemically active salts thereof, and their use for controlling phytopathogenic harmful fungi, and also processes for preparing compounds of the formula (I).

  公式（I）的噻唑基哌啶衍生物，其中符号A、G、Y、n、R1、R2、R3、R4和R5具有描述中给出的含义，以及其农药活性盐，以及其用于控制植物病原真菌的用途，以及制备公式（I）化合物的方法。
• Synthesis of chloroisoxazoline amino-acids
  作者：Jack E. Baldwin、Carolyn Hoskins、Lawrence Kruse

  DOI：10.1039/c39760000795

  日期：——

  esters yields the 3-chloroisoxazoline adducts, in an efficient reaction; further transformations convert these into the free aminoderivatives which are members of a class of biologically interesting amino-acids.

  加入氯腈氧化物与的氮酸盐盐αβ -unsaturated- α -nitrocrotonic酯得到3- chloroisoxazoline加合物，以有效的反应; 进一步的转化将它们转化为游离的氨基衍生物，其是一类生物学上感兴趣的氨基酸的成员。