2,2,3,3-tetrafluoropropyl chloroformate | 54777-38-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 2,2,3,3-tetrafluoropropyl chloroformate
• 英文别名: 2,2,3,3-Tetrafluorpropyl-chloroformat；1,1,3-Trihydroperfluoropropyl chloroformate；2,2,3,3-tetrafluoropropyl carbonochloridate
• CAS: 54777-38-7
• 化学式: C₄H₃ClF₄O₂
• 分子量: 194.513
• InChiKey: VCTKESLGCGNOFW-UHFFFAOYSA-N

物化性质

• 沸点：
  35 °C(Press: 32 Torr)
• 密度：
  1.5179 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,3,3-tetrafluoropropyl chloroformate 在 sodium peroxide 作用下， 反应 2.0h， 以78%的产率得到di(1,1,3-trihydroperfluoropropyl)peroxydicarbonate
  参考文献：
  名称：

  Synthesis and properties of di(polyfluoroalkyl) peroxydicarbonates

  摘要：

  Synthesis of di(polyfluoroalkyl)peroxydicarbonates [X(CF(2)) (n) CH(2)OC(O)O](2), where X = H, F; n = 1, 2, 4, 6 (yield 80%) involves the step of the chloroformate formation (yield up to 93%) via the phosgenation of polyfluorinated alcohols followed by the reaction with sodium peroxide. The rate constant of monomolecular decomposition k (term) was found to decrease as the polyfluoroalkyl groups were incorporated into the peroxide: it equaled 3.30 and 3.10 s(-1) for X = H, n = 2 and 4, respectively, and 7.36 s(-1) for di-n-butylperoxydicarbonate. The new peroxides are a source of the polyfluoroalkoxy radicals and nano-modifiers of the polymers to improve their heat resistance and light stability.

  DOI：

  10.1134/s1070363211050100
• 作为产物：
  描述：

  光气 、 四氟丙醇 在 amine 作用下， 以 乙醚 为溶剂， 反应 3.75h， 以78%的产率得到2,2,3,3-tetrafluoropropyl chloroformate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of new derivatives of 2-substituted-6-fluorobenzo[d]thiazoles as cholinesterase inhibitors

  摘要：

  A series of novel cholinesterase inhibitors based on 2-substituted 6-fluorobenzo[d]thiazole were synthesised and characterised by IR, H-1, C-13 and F-19 NMR spectroscopy and HRMS. Purity was checked by elemental analyses. The novel carbamates were tested for their ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The toxicity of the most active compounds was investigated using a standard in vitro test with HepG2 cells, and the ratio between biological activity and toxicity was determined. In addition, the toxicity of the most active compounds was evaluated against MCF7 cells using the xCELLigence system. Structure-activity relationships reflecting the dependence of cholinesterase inhibitors on the lipophilicity of the compounds as well as on the Taft polar and steric substituent constants are discussed. The specific orientation of the inhibitors in the binding site of acetylcholinesterase was determined using molecular docking of the most active compound. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.052

文献信息

• Herbicidal fluorinated carbonates
  申请人：PPG Industries, Inc.

  公开号：US04022609A1

  公开（公告）日：1977-05-10

  Fluorinated carbonates are described which are useful as miticides. These carbonates often possess herbicidal, insecticidal, and/or fungicidal properties. Examples of the fluorinated carbonates are 2',4'-dinitro-6'-sec-butylphenyl-2,2,2-trifluoroethyl carbonate; 2',4'-dinitro-6'-sec-butylphenyl-2,2,3,3-tetrafluoropropyl carbonate and 2',4'-dinitro-6'-cyclohexylphenyl 2,2,3,3-tetrafluoropropyl carbonate.

  氟化碳酸盐被描述为有用的杀螨剂。这些碳酸盐通常具有除草、杀虫和/或杀真菌的特性。氟化碳酸盐的例子包括2',4'-二硝基-6'-叔丁基苯基-2,2,2-三氟乙基碳酸酯；2',4'-二硝基-6'-叔丁基苯基-2,2,3,3-四氟丙基碳酸酯和2',4'-二硝基-6'-环己基苯基-2,2,3,3-四氟丙基碳酸酯。
• Synthesis, structural characterization, docking, lipophilicity and cytotoxicity of 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-alkyl carbamates, novel acetylcholinesterase and butyrylcholinesterase pseudo-irreversible inhibitors
  作者：Vladimír Pejchal、Šárka Štěpánková、Marcela Pejchalová、Karel Královec、Radim Havelek、Zdeňka Růžičková、Haresh Ajani、Rabindranath Lo、Martin Lepšík

  DOI：10.1016/j.bmc.2016.02.033

  日期：2016.4

  confirmed by optical rotation measurements. The synthesized compounds were evaluated for their AChE and BChE inhibitory activities. In addition, the cytotoxicity of the most active compounds was investigated against human cell lines employing XTT tetrazolium salt reduction assay and xCELLigence system allowing a label-free assessment of the cells proliferation. Our results demonstrated that the inhibitory mechanism

  在当前的研究中，合成了十六种新颖的（R）-1-（6-氟苯并[ d ]噻唑-2-基）乙胺衍生物作为乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）抑制剂。化学结构以及合成化合物的纯度由IR，1 H，13 C，19证实F NMR，高分辨率质谱和元素分析。通过旋光度测量确认光学活性。评价合成的化合物的AChE和BChE抑制活性。此外，使用XTT四唑盐减量测定法和xCELLigence系统研究了最具活性的化合物对人细胞的细胞毒性，该方法可对细胞增殖进行无标记评估。我们的结果表明，与以前对氨基甲酸酯的研究一致，该抑制机制被证实是伪不可逆的。表示为3b，3d，3l和3n的化合物在所有评估的化合物中均显示出最佳的AChE抑制活性，且效力比标准药物卡巴拉汀大10倍之多。使用最先进的共价对接和评分方法确定结合模式。获得的数据清楚地表明，苯并噻唑氨基甲酸酯的3b，3d，3l和3n具有对AChE和BChE的高
• Catalytic synthesis of polyfluoroalkyl chloroformates
  作者：A. I. Rakhimov、L. A. Butkovskaya、A. V. Baklanov

  DOI：10.1134/s1070363208050289

  日期：2008.5
• Orlov, S. I.; Chimishkyan, A. L.; Elinevskii, A. V., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 3, p. 417 - 420
  作者：Orlov, S. I.、Chimishkyan, A. L.、Elinevskii, A. V.、Grabarnik, M. S.

  DOI：——

  日期：——
• RAXIMOV, A. I.;BAKLANOV, A. V.;BUTKOVSKAYA, L. A.;ZEGELMAN, V. I.;POPOV, +
  作者：RAXIMOV, A. I.、BAKLANOV, A. V.、BUTKOVSKAYA, L. A.、ZEGELMAN, V. I.、POPOV, +

  DOI：——

  日期：——