[(E,3R)-1-(1,3,2-benzodioxaborol-2-yl)oct-1-en-3-yl]oxy-tert-butyl-dimethylsilane | 864516-81-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: [(E,3R)-1-(1,3,2-benzodioxaborol-2-yl)oct-1-en-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 864516-81-4
• 化学式: C₂₀H₃₃BO₃Si
• 分子量: 360.377
• InChiKey: KOXOAGXGXCMNFL-INFVRCAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [(E,3R)-1-(1,3,2-benzodioxaborol-2-yl)oct-1-en-3-yl]oxy-tert-butyl-dimethylsilane 在 N-溴代丁二酰亚胺(NBS) 作用下， 以80%的产率得到[(R)-1-((E)-2-Bromo-vinyl)-hexyloxy]-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Design and synthesis of benzo-lipoxin A4 analogs with enhanced stability and potent anti-inflammatory properties

  摘要：

  A new class of chemically and metabolically stable lipoxin analogs featuring a replacement of the tetraene unit of native LXA(4) with a substituted benzo-fused ring system have been designed and studied. These molecules were readily synthesized via a convergent synthetic route involving iterative palladium-mediated cross-coupling, and exhibit enhanced chemical stability, as well as resistance to metabolic inactivation via eicosanoid oxido-reductase. These new LX analogs were evaluated in a model of acute inflammation and were shown to exhibit potent anti-inflammatory properties, significantly decreasing neutrophil infiltration in vivo. The most potent among these was compound 9 (o-[9,12]-benzo-15-epi-LXA(4) methyl ester. Taken together, these findings help identify a new class of stable and easily prepared LX analogs that may serve as novel tools and as promising leads for new anti-inflammatory agents with improved therapeutic pro. le. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.013
• 作为产物：
  描述：

  (R)-tert-butyldimethyl(oct-1-yn-3-yloxy)silane 、 儿萘酚硼烷 在 儿萘酚硼烷 作用下， 生成 [(E,3R)-1-(1,3,2-benzodioxaborol-2-yl)oct-1-en-3-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Benzo lipoxin analogues

  摘要：

  提供苯唑类似物，其制备方法以及含有该化合物的药物组合物。这些化合物和组合物可用于治疗各种疾病，包括炎症、自身免疫疾病和异常细胞增殖等方法。

  公开号：

  US07683193B2
• 作为试剂：
  描述：

  (5S,6R,E)-methyl 8-(2-bromophenyl)-5,6-bis(tert-butyldimethylsilyloxy)oct-7-enoate 、 [(E,3R)-1-(1,3,2-benzodioxaborol-2-yl)oct-1-en-3-yl]oxy-tert-butyl-dimethylsilane 在 [(E,3R)-1-(1,3,2-benzodioxaborol-2-yl)oct-1-en-3-yl]oxy-tert-butyl-dimethylsilane 作用下， 以40的产率得到(5S,6R,E)-methyl 5,6-bis(tert-butyldimethylsilyloxy)-8-(2-((R,E)-3-(tert-butyldimethylsilyloxy)oct-1-enyl)phenyl)oct-7-enoate
  参考文献：
  名称：

  Benzo lipoxin analogues

  摘要：

  提供苯唑类似物，其制备方法以及含有该化合物的药物组合物。这些化合物和组合物可用于治疗各种疾病，包括炎症、自身免疫疾病和异常细胞增殖等方法。

  公开号：

  US07683193B2