diisopropyl (chloromethane)boranate | 83622-37-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: diisopropyl (chloromethane)boranate
• 英文别名: diisopropyl chloromethylboronate；diisopropyl chloromethyl borate；Diisopropyl (chloromethyl)boronate；chloromethyl-di(propan-2-yloxy)borane
• CAS: 83622-37-1
• 化学式: C₇H₁₆BClO₂
• 分子量: 178.467
• InChiKey: IGBWDEWJQHRLBM-UHFFFAOYSA-N

物化性质

• 沸点：
  65-70 °C(Press: 20 Torr)
• 密度：
  0.934±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diisopropyl (chloromethane)boranate 、 (1R,2R)-(-)-1,2-二环己基-1,2-乙二醇 以 正己烷 为溶剂， 以100%的产率得到(4R,5R)-2-chloromethyl-4,5-dicyclohexyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Hoffmann, Reinhard W.; Ditrich, Klaus; Koester, Gerhard, Chemische Berichte, 1989, vol. 122, p. 1783 - 1790

  摘要：

  DOI：
• 作为产物：
  描述：

  二氯甲基二异丙氧基硼烷 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以>95的产率得到diisopropyl (chloromethane)boranate
  参考文献：
  名称：

  Preparation of halomethaneboronates

  摘要：

  DOI：

  10.1016/s0022-328x(00)85850-7

文献信息

• [EN] NOVEL CYCLIC BORONATE INHIBITORS OF HCV REPLICATION<br/>[FR] NOUVEAUX INHIBITEURS DE BORONATE CYCLIQUES DE RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2009046098A1

  公开（公告）日：2009-04-09

  Compounds of formula (I) or a salt thereof are provided; wherein R1, R2, R3, R4, R6, R8, R20, R30, Y, Z and n are as defined in the description. Uses of the compounds as medicaments, and in the manufacture of medicaments for treating viral infection, especially HCV infection are also disclosed. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof.

  提供了化学式（I）的化合物或其盐；其中R1、R2、R3、R4、R6、R8、R20、R30、Y、Z和n的定义如描述中所述。还公开了将这些化合物用作药物以及用于治疗病毒感染，特别是HCV感染的药物制造中的用途。该发明还包括制备这些化合物和其药物配方的过程。
• Synthesis and evaluation of novel α-amino cyclic boronates as inhibitors of HCV NS3 protease
  作者：Xianfeng Li、Yong-Kang Zhang、Yang Liu、Charles Z. Ding、Qun Li、Yasheen Zhou、Jacob J. Plattner、Stephen J. Baker、Xuelei Qian、Dazhong Fan、Liang Liao、Zhi-Jie Ni、Gemma V. White、Jackie E. Mordaunt、Linos X. Lazarides、Martin J. Slater、Richard L. Jarvest、Pia Thommes、Malcolm Ellis、Colin M. Edge、Julia A. Hubbard、Don Somers、Paul Rowland、Pamela Nassau、Bill McDowell、Tadeusz J. Skarzynski、Wieslaw M. Kazmierski、Richard M. Grimes、Lois L. Wright、Gary K. Smith、Wuxin Zou、Jon Wright、Lewis E. Pennicott

  DOI：10.1016/j.bmcl.2010.04.129

  日期：2010.6

  We have designed and synthesized a novel series of alpha-amino cyclic boronates and incorporated them successfully in several acyclic templates at the P1 position. These compounds are inhibitors of the HCV NS3 serine protease, and structural studies show that they inhibit the NS3 protease by trapping the Ser-139 hydroxyl group in the active site. Synthetic methodologies and SARs of this series of compounds are described.
• Novel macrocyclic HCV NS3 protease inhibitors derived from α-amino cyclic boronates
  作者：Xianfeng Li、Yong-Kang Zhang、Yang Liu、Charles Z. Ding、Yasheen Zhou、Qun Li、Jacob J. Plattner、Stephen J. Baker、Suoming Zhang、Wieslaw M. Kazmierski、Lois L. Wright、Gary K. Smith、Richard M. Grimes、Renae M. Crosby、Katrina L. Creech、Luz H. Carballo、Martin J. Slater、Richard L. Jarvest、Pia Thommes、Julia A. Hubbard、Maire A. Convery、Pamela M. Nassau、William McDowell、Tadeusz J. Skarzynski、Xuelei Qian、Dazhong Fan、Liang Liao、Zhi-Jie Ni、Lewis E. Pennicott、Wuxin Zou、Jon Wright

  DOI：10.1016/j.bmcl.2010.08.022

  日期：2010.10

  A novel series of P2-P4 macrocyclic HCV NS3/4A protease inhibitors with α-amino cyclic boronates as warheads at the P1 site was designed and synthesized. When compared to their linear analogs, these macrocyclic inhibitors exhibited a remarkable improvement in cell-based replicon activities, with compounds 9a and 9e reaching sub-micromolar potency in replicon assay. The SAR around α-amino cyclic boronates clearly established the influence of ring size, chirality and of the substitution pattern. Furthermore, X-ray structure of the co-crystal of inhibitor 9a and NS3 protease revealed that Ser-139 in the enzyme active site traps boron in the warhead region of 9a, thus establishing its mode of action.
• (Chloromethyl)lithium: efficient generation and capture by boronic esters and a simple preparation of diisopropyl (chloromethyl)boronate
  作者：Kizhakethil Mathew. Sadhu、Donald S. Matteson

  DOI：10.1021/om00128a038

  日期：1985.9.1
• SADHU, KIZHAKETHIL, MATHEW;MATTESON, D. S., ORGANOMETALLICS, 1985, 4, N 9, 1687-1689
  作者：SADHU, KIZHAKETHIL, MATHEW、MATTESON, D. S.

  DOI：——

  日期：——