[(R)-1-((E)-2-Bromo-vinyl)-hexyloxy]-tert-butyl-dimethyl-silane | 102228-24-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(R)-1-((E)-2-Bromo-vinyl)-hexyloxy]-tert-butyl-dimethyl-silane
• 英文别名: [(E,3R)-1-bromooct-1-en-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 102228-24-0
• 化学式: C₁₄H₂₉BrOSi
• 分子量: 321.373
• InChiKey: MMASSONNBDZKGH-XZHRJIJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [(R)-1-((E)-2-Bromo-vinyl)-hexyloxy]-tert-butyl-dimethyl-silane 在 盐酸 、 正丙胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 水 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 methyl (5S,6R,7E,9E,13E,15R)-5,6,15-trihydroxyicosa-7,9,13-trien-11-ynoate
  参考文献：
  名称：

  Total synthesis of aspirin-triggered 15-epi-lipoxin A4

  摘要：

  The total synthesis of aspirin-triggered 15-epi-LXA(4) has been achieved using a chiral pool strategy for the C1-C12 fragment starting from 2-deoxy-D-ribose. Sharpless catalytic AE generated the C15 chiral center with > 98% ee. The stereospecific (Z)-reduction of the conjugated trienyne to the tetraene was achieved with Zn(Cu, Ag) in aq. CH3OH at aq. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01187-x
• 作为产物：
  描述：

  (R)-(+)-1-辛炔-3-醇 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 三氯化铝 、 silver nitrate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 [(R)-1-((E)-2-Bromo-vinyl)-hexyloxy]-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Total synthesis of aspirin-triggered 15-epi-lipoxin A4

  摘要：

  The total synthesis of aspirin-triggered 15-epi-LXA(4) has been achieved using a chiral pool strategy for the C1-C12 fragment starting from 2-deoxy-D-ribose. Sharpless catalytic AE generated the C15 chiral center with > 98% ee. The stereospecific (Z)-reduction of the conjugated trienyne to the tetraene was achieved with Zn(Cu, Ag) in aq. CH3OH at aq. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01187-x

文献信息

• Stereocontrolled total synthesis of (5Z,8Z11Z,13E)(15S)-15-hydroxyeicosa-5,8,11,13-tetraenoic acid (15S-HETE) and analogues
  作者：K. C. Nicolaou、Tamara Ladduwahetty、E. Michael Elisseou

  DOI：10.1039/c39850001580

  日期：——

  A novel and stereoselective synthesis of 15S-HETE and a number of analogues based on CuI–Pd0 coupling reaction is described.

  描述了一种新颖且立体选择性的15 S -HETE和许多基于Cu I -Pd 0偶联反应的类似物的合成方法。
• Design and synthesis of benzo-lipoxin A4 analogs with enhanced stability and potent anti-inflammatory properties
  作者：Nicos A. Petasis、Raquel Keledjian、Yee-Ping Sun、Kalyan C. Nagulapalli、Eric Tjonahen、Rong Yang、Charles N. Serhan

  DOI：10.1016/j.bmcl.2008.01.013

  日期：2008.2

  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.