(R)-(5-bromopent-1-en-4-yn-3-yloxy)(tert-butyl)dimethylsilane | 1350928-53-8

• 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)-(5-bromopent-1-en-4-yn-3-yloxy)(tert-butyl)dimethylsilane
• CAS: 1350928-53-8
• 化学式: C₁₁H₁₉BrOSi
• 分子量: 275.261
• InChiKey: HSYYICYJXOEBMI-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((4R,5S)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-yn-1-ol 、 (R)-(5-bromopent-1-en-4-yn-3-yloxy)(tert-butyl)dimethylsilane 在 盐酸羟胺 、 copper(l) chloride 作用下， 以 甲醇 为溶剂， 反应 1.17h， 以52%的产率得到(1R,6R)-6-(tert-butyldimethylsilyloxy)-1-((4R,5S)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)oct-7-ene-2,4-diyn-1-ol
  参考文献：
  名称：

  A flexible organocatalytic enantioselective synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its congeners

  摘要：

  A unified enantioselective route is developed for the synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its synthetic congeners. A proline-catalyzed aminoxylation, cross-metathesis, Wittig reaction, and catalytic dihydroxylation are key steps of this synthesis. This new approach is envisioned to facilitate the synthesis of every representative member of the family with skeletal and stereochemical variation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.058
• 作为产物：
  描述：

  (R)-5-(trimethylsilyl)pent-1-en-4-yn-3-ol 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.0h， 生成 (R)-(5-bromopent-1-en-4-yn-3-yloxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  A flexible organocatalytic enantioselective synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its congeners

  摘要：

  A unified enantioselective route is developed for the synthesis of heptadeca-1-ene-4,6-diyne-3S,8R,9S,10S-tetrol and its synthetic congeners. A proline-catalyzed aminoxylation, cross-metathesis, Wittig reaction, and catalytic dihydroxylation are key steps of this synthesis. This new approach is envisioned to facilitate the synthesis of every representative member of the family with skeletal and stereochemical variation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.058