(1S,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
• 英文别名: (1S,5R,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
• 化学式: C₁₀H₁₃BrO₃
• 分子量: 261.115
• InChiKey: XXLWKJYZTYWDNT-QUNWWBBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (1S,2S,3R)-(2-bromomethyl-3-hydroxymethyl-2,3-dimethylcyclopentyl)methanol
  参考文献：
  名称：

  A new hydroxydiphosphine as a ligand for Rh(I)-catalyzed enantioselective hydrogenation

  摘要：

  A new diphosphine ligand bearing a hydroxy group in the backbone was synthesized starting from 9-bromocamphor. The rhodium(I) complex based on this ligand was tested in the hydrogenation of alpha- and beta-amino acid precursors. The activity and selectivity of the catalyst were found to be strongly dependent upon the nature of the substrate. Thus. beta-acetylamino carboxylates were obtained with up to 97% ee. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00372-5
• 作为产物：
  描述：

  (1S,7S)-7-(bromomethyl)-1,7-dimethylbicyclo[2.2.1]heptane-2,3-dione 在 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 (1S,8S)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
  参考文献：
  名称：

  A new hydroxydiphosphine as a ligand for Rh(I)-catalyzed enantioselective hydrogenation

  摘要：

  A new diphosphine ligand bearing a hydroxy group in the backbone was synthesized starting from 9-bromocamphor. The rhodium(I) complex based on this ligand was tested in the hydrogenation of alpha- and beta-amino acid precursors. The activity and selectivity of the catalyst were found to be strongly dependent upon the nature of the substrate. Thus. beta-acetylamino carboxylates were obtained with up to 97% ee. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00372-5

文献信息

• A new hydroxydiphosphine as a ligand for Rh(I)-catalyzed enantioselective hydrogenation
  作者：Igor V. Komarov、Axel Monsees、Renat Kadyrov、Christine Fischer、Ute Schmidt、Armin Börner

  DOI：10.1016/s0957-4166(02)00372-5

  日期：2002.8

  A new diphosphine ligand bearing a hydroxy group in the backbone was synthesized starting from 9-bromocamphor. The rhodium(I) complex based on this ligand was tested in the hydrogenation of alpha- and beta-amino acid precursors. The activity and selectivity of the catalyst were found to be strongly dependent upon the nature of the substrate. Thus. beta-acetylamino carboxylates were obtained with up to 97% ee. (C) 2002 Published by Elsevier Science Ltd.