1-Diazo-3-((1R,2S,3S,4R,5S)-2,4-dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-3-yl)-propan-2-one | 677309-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Diazo-3-((1R,2S,3S,4R,5S)-2,4-dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-3-yl)-propan-2-one
• CAS: 677309-22-7
• 化学式: C₁₅H₂₆N₂O₃Si
• 分子量: 310.469
• InChiKey: DXILGFSXWHOOSQ-OPTZYUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  71.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-Diazo-3-((1R,2S,3S,4R,5S)-2,4-dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-3-yl)-propan-2-one 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(1R,2R,6R,7R,8S)-2,7-Dimethyl-6-trimethylsilanyloxy-11-oxa-tricyclo[6.2.1.0^2,6]undecan-4-one
  参考文献：
  名称：

  Desymmetrizations of meso oxabicyclic compounds by asymmetric C–H insertion

  摘要：

  meso Oxabicyclo[3.2.1]diazoketones underwent intramolecular C-H bond insertion to generate oxatricyclic compounds bearing fused cyclopentanones upon reaction with rhodium catalysts. Using the chiral catalyst Rh-2(S-BPTTL)(4), 44% ee was achieved in this desymmetrization reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.055
• 作为产物：
  描述：

  (1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 、 三乙胺 、 lithium hexamethyldisilazane 、 氯甲酸异丁酯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 1-Diazo-3-((1R,2S,3S,4R,5S)-2,4-dimethyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-3-yl)-propan-2-one
  参考文献：
  名称：

  Desymmetrizations of meso oxabicyclic compounds by asymmetric C–H insertion

  摘要：

  meso Oxabicyclo[3.2.1]diazoketones underwent intramolecular C-H bond insertion to generate oxatricyclic compounds bearing fused cyclopentanones upon reaction with rhodium catalysts. Using the chiral catalyst Rh-2(S-BPTTL)(4), 44% ee was achieved in this desymmetrization reaction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.055

文献信息

• Desymmetrization of meso [3.2.1]oxabicyclic systems using metal-catalysed asymmetric intramolecular C–H insertion
  作者：Xiaomei Zhang、Zhengning Li、John C.K. Chu、Pauline Chiu

  DOI：10.1016/j.tetlet.2011.10.026

  日期：2011.12

  Diazoketone derivatives of meso 8-oxabicyclo[3.2.1]octen-3-ones were desymmetrized by an intramolecular C-H insertion mediated by chiral copper and dirhodium catalysts to generate oxatricyclic systems with up to 5 contiguous stereogenic centres and 50% ee. (C) 2011 Elsevier Ltd. All rights reserved.