3,3,3-三氟-2-重氮基丙酰氯 | 59733-92-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 3,3,3-三氟-2-重氮基丙酰氯
• 英文名称: 2-diazo-3,3,3-trifluoropropanoyl chloride
• 英文别名: 2-diazo-3,3,3-trifluoropropionyl chloride；2-diazotrifluoropropionyl chloride；(2Z)-2-diazo-3,3,3-trifluoropropanoyl chloride
• CAS: 59733-92-5
• 化学式: C₃ClF₃N₂O
• 分子量: 172.494
• InChiKey: KRAIXOVJMIYWMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3,3-三氟-2-重氮基丙酰氯 、 异戊烯醇 在 吡啶 作用下， 反应 2.5h， 以64%的产率得到1-(2-diazo-3,3,3-trifluoropropionyloxy)-3-methyl-2-butene
  参考文献：
  名称：

  含有重氮三氟丙酰基的含二磷酸法呢酯的光活性类似物的合成、性质和应用，该类似物含有用于增强稳定性的修饰键

  摘要：

  法呢基二磷酸 (FPP) 的光活性类似物是研究使用该分子作为底物的酶的有用探针。在这里，我们描述了两种新的 FPP 类似物的制备和性质，它们包含通过酰胺或酯键连接到香叶基二磷酸的重氮三氟丙酰基光团。酰胺连接的类似物 ( 3 ) 以32 P 标记的形式从香叶醇中分七个步骤合成。用酿酒酵母蛋白法呢基转移酶 (ScPFTase) 进行的实验表明 3 是该酶的替代底物。[ 32]光解实验P]3 表明该化合物标记了法呢基转移酶和香叶基香叶基转移酶（1 型和 2 型）的 β 亚基。然而，酰胺连接的探针 3 在长期储存后会发生重排，变成不具有光化学反应性的异构三唑酮，因此使用不便。为了解决这个稳定性问题，从香叶醇中分六个步骤制备了酯连接的类似物4。计算分析和 X 射线晶体学研究表明，4以与 FPP 类似的方式与蛋白质法呢基转移酶 (PFTase) 结合。化合物4也是 PFTase 的替代底物，32 P 标记的形式选择性地光交联

  DOI：

  10.1111/j.1747-0285.2009.00914.x
• 作为产物：
  描述：

  光气 、 2-重氮基-1,1,1-三氟乙烷 在 dipotassium hydrogenphosphate 作用下， 以 二氯甲烷 为溶剂， 生成 3,3,3-三氟-2-重氮基丙酰氯
  参考文献：
  名称：

  Diazotrifluoropropionamido-Containing Prenylcysteines:  Syntheses and Applications for Studying Isoprenoid−Protein Interactions

  摘要：

  [GRAPHICS]Photoaffinity-labeled prenylcysteines (1 and 2) incorporating a diazotrifluoropropionamide-based photophore have been prepared. Photolyses of 2 in the presence of RhoGDI, a protein that interacts with prenylated proteins, and prenylcysteine-containing competitors demonstrate the effectiveness of this photoaffinity-labeled analogue as a tool for studying isoprenoid binding sites.

  DOI：

  10.1021/ol026752a

文献信息

• Preparation and properties of some photolabile sugar derivatives for affinity labelling
  作者：Gerhart Kurz、Jochen Lehmann、Roland Thieme

  DOI：10.1016/0008-6215(85)85191-0

  日期：1985.2

  Abstract Sugar derivatives carrying various photolabile groups at various positions have been synthesised, namely, 4-azido-4-deoxy- d -galactose, 4-azi-4-deoxy- d -xylo-hexopyranose (4), 3,7-anhydro-2-azi-1,2-dideoxy- d -glycero- l -manno-octitol (6), and 3-azi-1-methoxybutyl β- d -glucopyranoside (8), and 4-(2-diazo-3,3,3-trifluoropropionyl)- d -glucose. They were tested for their applicability in

  摘要合成了在不同位置带有不同光不稳定基团的糖衍生物，即4-叠氮基4-脱氧-d-半乳糖，4-叠氮基4-脱氧-d-木糖己糖（4），3,7-脱水-2-azi-1,2-二脱氧-d-甘油-1-甘露辛醇（6）和3-azi-1-甲氧基丁基β-d-吡喃葡萄糖苷（8）和4-（2-重氮-3 ，3，3-三氟丙酰基）-d-葡萄糖。对它们在糖结合蛋白的光亲和标记中的适用性进行了测试，使用重氮基衍生物4、6和8获得了最佳的照射波长和光解衰减速率的结果。
• Chemistry of naturally occurring polyamines. 9. Synthesis of spermidine and spermine photoaffinity labeling reagents
  作者：Srinivasan Nagarajan、Bruce Ganem

  DOI：10.1021/jo00350a059

  日期：1985.12
• Studies on Ca2+ channel antagonists. A 2-diazo-3,3,3-trifluoropropionamide derivative related to verapamil as a potential photoaffinity probe
  作者：Louis J. Theodore、Wendel L. Nelson、Bharti Dave、John C. Giacomini

  DOI：10.1021/jm00164a064

  日期：1990.2

  2-(3,4-Dimethoxyphenyl)-2-isopropyl-5-[N-[4-(N-methyl-2-diazo- 3,3,3-trifluoropropionamido)phenethyl]methyl-amino]valeronitril e (3), a potential photoaffinity probe for Ca2+ channels related to verapamil (1), was prepared from N-methyl-4-nitrophenethylamine (7) and 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-(methanesulfonoxy)valeron itrile (12). Compound 3 showed concentration-dependent negative inotropic effects in rat right myocardial ventricular strips, EC50 = (1.05 +/- 0.33) X 10(-7) M (mean +/- SD), being slightly less potent than gallopamil (2), EC50 = (2.18 +/- 0.66) X 10(-8) M. It displaced [3H]gallopamil in myocardial membranes, Ki = (3.76 +/- 1.55) X 10(-8) M, compared to 2, Ki = (1.55 +/- 0.16) X 10(-8) M. Photoactivation at 265 nm reduced the recoverable binding of [3H]gallopamil to 26% compared to no effect on 2. This agent may be a useful photoaffinity probe to aid in further characterization of Ca2+ channels.
• Synthesis of Radiolabeled Juvenile Hormone Analogs and Chiral Homologs
  作者：Wai-Si Eng、Glenn D. Prestwich

  DOI：10.1002/bscb.19860950913

  日期：——

  AbstractRadiolabeled juvenile hormone (JHs) and labeled JH derivatives are required for the study of JH metabolism and JH‐protein interactions as well as JH radioimmunoassay in insects. The progress in the synthesis of these labeled compounds for the last five years is reviewed, including the preparation of photoaffinity labels, enantiomerically enriched JH I and JH II with 3H labels, and radioiodinated analogs of JH I, methoprene and phenoxyphenyl ether insect growth regulators (IGRs). Experimental details are given for the efficient synthesis of two 3H‐labeled photoactivatable JH analogs, EFDA and EFTP, their photolysis in methanol, and their competitive binding assays performed on the Manduca sexta JH binding proteins (JHBP).
• Synthesis, photochemical reactions, and tubulin binding of novel photoaffinity labeling derivatives of colchicine
  作者：Marianne E. Staretz、Susan Bane Hastie

  DOI：10.1021/jo00058a051

  日期：1993.3