2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)acetic acid | 148058-40-6

• 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: 2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)acetic acid
• 英文别名: 4-((trifluoromethyl)diazirinyl)phenylacetic acid；4-(3-fluoromethyldiazirin-3-yl)phenylacetic acid；4-(1-azi-2,2,2-trifluoroethyl)phenylacetic acid；2-[4-[3-(trifluoromethyl)diazirin-3-yl]phenyl]acetic acid
• CAS: 148058-40-6
• 化学式: C₁₀H₇F₃N₂O₂
• 分子量: 244.173
• InChiKey: ILMVLFNNVDOUFY-UHFFFAOYSA-N

物化性质

• 沸点：
  323.3±52.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)acetic acid 在 盐酸 、 氯化亚砜 、 氢溴酸 、 氧气 、 sodium acetate 、 silver nitrate 、 二甲基亚砜 作用下， 以 乙醚 、 乙醇 、 水 、 二甲基亚砜 、 乙腈 、 苯 为溶剂， 反应 47.0h， 生成 3-benzyl-5-(4-hydroxyphenyl)-2-<4-(1-azi-2,2,2-trifluoroethyl)phenylacetamido>pyrazine
  参考文献：
  名称：

  Chen, Feng Qi; Zheng, Jing Ling; Hirano, Takashi, Journal of the Chemical Society. Perkin transactions I, 1995, # 17, p. 2129 - 2134

  摘要：

  DOI：
• 作为产物：
  描述：

  O-叔-丁基二甲基硅烷基-苄醇4-(2,2,2-三氟乙烷酮) 在 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 盐酸羟胺 、 四丁基氟化铵 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.25h， 生成 2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)acetic acid
  参考文献：
  名称：

  SMALL MOLECULE MODULATORS OF PCSK9 AND METHODS OF USE THEREOF

  摘要：

  公式（I）的化合物：或其药用可接受的盐、水合物、溶剂合物、或其拉克米混合物或立体异构体，以及使用这种化合物预防或治疗LDL胆固醇相关疾病或紊乱的方法，以及包含这种化合物的试剂盒和组合物。

  公开号：

  US20160031935A1

文献信息

• 3-Benzyl-5-(4-hydroxyphenyl)-2-[4-(1-azi-2,2,2-trifluoroethyl)phenylacetamido]pyrazine, a Photoreactive Analogue of Coelenteramide. Synthesis and Photolysis
  作者：Feng Qi Chen、Takashi Hirano、Mamoru Ohashi、Hitoshi Nakayama、Kazuaki Oda、Minoru Machida

  DOI：10.1246/cl.1993.287

  日期：1993.2

  A photoreactive analogue of coelenteramide (light emitting species in aequorin bioluminescence) has been synthesized for photoaffinity labeling studies of aequorin. Photolysis of this compound in methanol gave a formal OH insertion product in 62% yield without damage of the main skeleton of coelenteramide, indicating a potential use for mapping the coelenterazine binding site in aequorin.

  已经合成了腔肠酰胺（水母发光蛋白生物发光中的发光物质）的光反应类似物，用于水母发光蛋白的光亲和标记研究。该化合物在甲醇中光解，得到正式的 OH 插入产物，产率 62%，且不会损坏腔肠酰胺的主骨架，这表明其可用于绘制水母发光蛋白中腔肠素结合位点的潜在用途。
• Synthesis and preliminary chemie- and bio-iuminescence studies of a novel photolabile coelenterazine analogue with a trifluoromethyl diazirine group
  作者：Feng-Qi Chen、Takashi Hirano、Yoshinobu Hashizume、Yoshihiro Ohmiya、Mamoru Ohashi

  DOI：10.1039/c39940002405

  日期：——

  A novel photolabile analogue of coelenterazine with a trifluoromethyl diazirine group is successfully synthesized for photoaffinity labelling of the active site of aequorin; preliminary studies on its chemi-and bio-luminescence demonstrate that the photolabile analogue shows the same luminescence properties and kinetics as those of natural coelenterazine and thus, it is deduced that both compounds occupy the same active site of aequorin.

  成功合成了一种带有三氟甲基重氮基团的新型光亲和性腔肠素类似物，用于对腔肠素的活性位点进行光亲和性标记；对其化学发光和生物发光的初步研究表明，该光亲和性类似物显示出与天然腔肠素相同的发光特性和动力学，因此推断这两种化合物占据了腔肠素的相同活性位点。
• Insecticidal Quinazoline Derivatives with (Trifluoromethyl)diazirinyl and Azido Substituents as NADH:Ubiquinone Oxidoreductase Inhibitors and Candidate Photoaffinity Probes
  作者：Bachir Latli、Edgardo Wood、John E. Casida

  DOI：10.1021/tx9501602

  日期：1996.1.1

  Two candidate photoaffinity probes are designed from 4-substituted quinazolines known to be potent insecticides/acaricides and NADH:ubiquinone oxidoreductase inhibitors acting at or near the rotenone site. 4-(11-Azidoundecyl-2-amino)quinazoline, based on the undecylamino analog SAN 548A as a prototype, was synthesized in 18% overall yield from ethyl 10-undecenoate by oxidation of the terminal double bond, reductive amination, coupling to 4-chloroquinazoline, and functional group manipulation of the terminal ethyl ester to an alcohol, a mesylate and finally nucleophilic displacement with azide ions. 4-(4-(3-(Trifluoromethyl)3H-diazirin-3-yl)phenethoxy)quinazoline [the (trifluoromethyl)diazirinyl analog of fenazaquin insecticide/acaricide] was prepared from 4-bromophenethyl alcohol in 31% overall yield by first introducing the trifluoromethylketone moiety followed by its conversion to the (trifluoromethyl)diazirine and finally coupling to 8-chloroquinazoline as above. Both candidate photoaffinity probes have the inhibitory potency of rotenone (IC50 Of 3-4 nM in each case). The azidoundecylamino compound has inadequate photoreactivity whereas that of the (trifluoromethyl)diazirinyl analog is ideal at 350 nm. Radiosynthesis of the latter photoaffinity ligand included introduction of the diazirinyl moiety as the carbene precursor, oxidation of (trifluoromethyl)diazirinylphenethyl alcohol to the corresponding acid with Jones' reagent, and reduction of the phenacetyl chloride intermediate with sodium borotritide to incorporate tritium.
• [EN] SMALL MOLECULE MODULATORS OF PCSK9 AND METHODS OF USE THEREOF<br/>[FR] MODULATEURS À PETITES MOLÉCULES DE PCSK9 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ADAERATA LTD PARTNERSHIP

  公开号：WO2014139008A1

  公开（公告）日：2014-09-18

  A compound of Formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or racemic mixture or stereoisomer thereof, and methods for preventing or treating an LDL-cholesterol-related disease or disorder using such compound(s), and kits and compositions comprising such compound(s).
• SMALL MOLECULE MODULATORS OF PCSK9 AND METHODS OF USE THEREOF
  申请人：ADAERATA, LIMITED PARTNERSHIP

  公开号：US20160031935A1

  公开（公告）日：2016-02-04

  A compound of Formula (I): or a pharmaceutically acceptable salt, hydrate, solvate, or racemic mixture or stereoisomer thereof, and methods for preventing or treating an LDL-cholesterol-related disease or disorder using such compound(s), and kits and compositions comprising such compound(s).

  公式（I）的化合物：或其药用可接受的盐、水合物、溶剂合物、或其拉克米混合物或立体异构体，以及使用这种化合物预防或治疗LDL胆固醇相关疾病或紊乱的方法，以及包含这种化合物的试剂盒和组合物。