(cyclobutylmethyl)magnesium chloride | 32251-57-3

• 分子结构分类: 有机化合物
• 英文名称: (cyclobutylmethyl)magnesium chloride
• CAS: 32251-57-3
• 化学式: C₅H₉ClMg
• 分子量: 128.884
• InChiKey: KMRWJCAVLYIWIL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  7.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (cyclobutylmethyl)magnesium chloride 在 HCl 、 AgBF₄ 作用下， 以 乙醚 、 二氯甲烷-D2 为溶剂， 生成 {(4-penten-1-yl-κ3,C1,4,5)(1,2-bis(dimethylphosphino)ethane)Pt(II)}BF4
  参考文献：
  名称：

  在螯合的（戊烯基）铂络合物中烯烃可逆地插入铂-碳键中的动力学和构象

  摘要：

  The synthesis and characterization, including detailed H-1, H-2, P-31, and C-13 NMR analysis of [(1,1-dideuterio-2,2-dimethyl-4-penten-1-yl-kappa3C1,4,5)(dmpe)PtII]BF4, 1-alpha-d2, and its 3,3-dideuterio isotopomer, 1-gamma-d2 (dmpe = 1,2-bis(dimethylphosphino)ethane), are described. Thermolysis of each 1-alpha-d2 and 1-gamma-d2 was carried out at 125-degrees-C in several solvents to yield a 1/1 mixture of 1-alpha-d2 and 1-gamma-d2. The rate of rearrangement is cleanly first order. Thermolysis of 1-alpha-d2 between 81 and 125-degrees-C in methylene chloride led to determinations of activation parameters, E(a) = 31.8(0.6) kcal/mol and DELTAS(double dagger) = -0.5(1.6) eu (100-degrees-C). An X-ray crystal structure determination was carried out on the compound. It crystallizes in the monoclinic space group P2(1)/n (No. 14), with a = 19.337(11) angstrom, b = 6.948(4) angstrom, c = 17.260(9) angstrom, beta = 122.34(6)degrees, V = 1959.3 angstrom, and Z = 4. The structure was solved with heavy atom techniques and refined to a final R factor of 4.18%. In the solid state, the coordinated vinyl group is slipped slightly out the plane of the molecule and is canted at a dihedral angle of 52-degrees from the molecular plane. The chelate ring shows only very slight distortions from a presumed strain-free shape. 2D NOESY spectra suggest that the in-plane conformation of the pentenyl chelate is at least partly populated in solution. (dmpe)Pt(CH2-c-C4H7)Cl, 11, was prepared. Thermolysis of 11 at 110-degrees-C yielded intractable metal-containing materials along with methylenecyclobutane and methylcyclobutane together in ca. 60% yield as the only identifiable organic products. Treatment of 11 with silver ion at low temperatures in acetone or methylene chloride yielded two products in a 1:7 (NMR) ratio, methylenecyclobutane and a material stable only below 0-degrees-C that is assigned the structure [(4-penten-1-yl-kappa3C1,4,5)(dmpe)PtII]BF4 on the basis of its NMR spectrum.

  DOI：

  10.1021/om00031a037

文献信息

• Potent inhibitors of HCV-NS3 protease derived from boronic acids
  作者：Srikanth Venkatraman、Wanli Wu、Andrew Prongay、Viyyoor Girijavallabhan、F. George Njoroge

  DOI：10.1016/j.bmcl.2008.10.124

  日期：2009.1

  Chronic hepatitis C infection is the leading causes for cirrhosis of the liver and hepatocellular carcinoma, leading to liver failure and liver transplantation. The etiological agent, HCV virus produces a single positive strand of RNA that is processed with the help of serine protease NS3 to produce mature virus. Inhibition of NS3 protease can be potentially used to develop effective drugs for HCV infections. Numerous efforts are now underway to develop potent inhibitors of HCV protease that contain ketoamides as serine traps. Herein we report the synthesis of a series of potent inhibitors that contain a boronic acid as a serine trap. The activity of these compounds were optimized to 200pM. X-ray structure of compound 17 bound to NS3 protease is also discussed.