4-(3-fluoromethyldiazirin-3-yl)phenylacetyl chloride | 160290-93-7

• 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: 4-(3-fluoromethyldiazirin-3-yl)phenylacetyl chloride
• 英文别名: 4-((trifluoromethyl)diazirinyl)phenacetyl chloride
• CAS: 160290-93-7
• 化学式: C₁₀H₆ClF₃N₂O
• 分子量: 262.619
• InChiKey: RMIUBDWWZFRKAL-UHFFFAOYSA-N

物化性质

• 沸点：
  290.1±50.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.79
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(3-fluoromethyldiazirin-3-yl)phenylacetyl chloride 在 氢溴酸 、 sodium acetate 、 silver nitrate 作用下， 以 乙醚 、 二甲基亚砜 、 乙腈 为溶剂， 反应 40.67h， 生成 2-oxo-3-<4-(3-fluoromethyldiazirin-3-yl)phenyl>propanal
  参考文献：
  名称：

  Synthesis and preliminary chemie- and bio-iuminescence studies of a novel photolabile coelenterazine analogue with a trifluoromethyl diazirine group

  摘要：

  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。

  DOI：

  10.1039/c39940002405
• 作为产物：
  描述：

  2-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)acetic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 14.0h， 生成 4-(3-fluoromethyldiazirin-3-yl)phenylacetyl chloride
  参考文献：
  名称：

  Synthesis and preliminary chemie- and bio-iuminescence studies of a novel photolabile coelenterazine analogue with a trifluoromethyl diazirine group

  摘要：

  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。

  DOI：

  10.1039/c39940002405

文献信息

• Study of the Structure–Activity Relationship of an Anti-Dormant Mycobacterial Substance 3-(Phenethylamino)Demethyl(oxy)aaptamine to Create a Probe Molecule for Detecting Its Target Protein
  作者：Yuji Sumii、Kentaro Kamiya、Takehiko Nakamura、Kenta Tanaka、Takumi Kaji、Junya Mukomura、Naoyuki Kotoku、Masayoshi Arai

  DOI：10.3390/md20020098

  日期：——

  The current tuberculosis treatment regimen is long and complex, and its failure leads to relapse and emergence of drug resistance. One of the major reasons underlying the extended chemotherapeutic regimen is the ability of Mycobacterium tuberculosis to attain a dormant state. Therefore, the identification of new lead compounds with chemical structures different from those of conventional anti-tuberculosis drugs is essential. The compound 3-(phenethylamino)demethyl(oxy)aaptamine (PDOA, 1), isolated from marine sponge of Aaptos sp., is known as an anti-dormant mycobacterial substance, and has been reported to be effective against the drug resistant strains of M. tuberculosis. However, its target protein still remains unclear. This study aims to clarify the structure–activity relationship of 1 using 15 synthetic analogues, in order to prepare a probe molecule for detecting the target protein of 1. We succeeded in creating the compound 15 with a photoaffinity group that retained antimicrobial activity, which proved to be a suitable probe molecule for identifying the target protein of 1.

  当前的结核病治疗方案是漫长且复杂的，治疗失败会导致复发并产生药物耐药性。导致化疗方案延长的一个主要原因是结核分枝杆菌能够进入休眠状态。因此，寻找化学结构与传统抗结核药物不同的新领先化合物至关重要。从海绵Aaptos sp.中分离出的3-(苯乙胺)去甲基(氧)阿普他明（PDOA, 1）化合物被称为一种抗休眠结核分枝杆菌物质，并已被报道对结核分枝杆菌的耐药菌株有效。然而，其靶蛋白仍然不清楚。本研究旨在通过使用15种合成类似物来澄清1的结构-活性关系，以制备一个用于检测1的靶蛋白的探针分子。我们成功地制备了一种带有光亲和性基团的化合物15，该化合物保留了抗微生物活性，被证明是用于识别1的靶蛋白的合适探针分子。
• 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.
• Chen, Feng Qi; Zheng, Jing Ling; Hirano, Takashi, Journal of the Chemical Society. Perkin transactions I, 1995, # 17, p. 2129 - 2134
  作者：Chen, Feng Qi、Zheng, Jing Ling、Hirano, Takashi、Niwa, Haruki、Ohmiya, Yoshihiro、Ohashi, Mamoru

  DOI：——

  日期：——