(1R,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione | 497261-97-9

• 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: (1R,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
• 英文别名: (1R,5S,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione
• CAS: 497261-97-9
• 化学式: C₁₀H₁₃BrO₃
• 分子量: 261.115
• InChiKey: XXLWKJYZTYWDNT-WHFVKQHSSA-N

物化性质

• 沸点：
  348.8±15.0 °C(Predicted)
• 密度：
  1.497±0.06 g/cm3(Predicted)

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：

  (1R,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione 在 四氯化碳 、 lithium aluminium tetrahydride 、 三溴化硼 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  CHIRAL INTERMEDIATES USEFUL FOR THE PREPARATION OF HYDROXYPHOSPHINE LIGANDS

  摘要：

  公式（I）的化合物，其中R1是氢或羟基保护基；R2和R3相同或不同，且独立地选择自卤素或—O—SO2—X；其中X是—C1-C4烷基；C1-C4烷基被一个或多个卤素取代；或被取代或未取代的苯基，其中所述苯基取代基被选择自卤素、硝基和C1-C4烷基；但当R3为溴时，X不是对甲苯基；以及其制备方法。

  公开号：

  US20130217900A1
• 作为产物：
  描述：

  (1R,7R)-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， 反应 3.6h， 以92%的产率得到(1R,8R)-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.
• CHIRAL INTERMEDIATES USEFUL FOR THE PREPARATION OF HYDROXYPHOSPHINE LIGANDS
  申请人：Shroff Jaidev Rajnikant

  公开号：US20130217900A1

  公开（公告）日：2013-08-22

  A compound of formula (I), wherein R 1 is hydrogen or a hydroxyl protecting group; and R 2 and R 3 are same or different and are independently selected from halogen or —O—SO 2 —X; wherein X is —C 1 -C 4 alkyl; C 1 -C 4 alkyl substituted with one or more halogen; or substituted or unsubstituted phenyl wherein said phenyl substituent is selected from halogen, nitro and C 1 -C 4 alkyl; provided that when R 3 is bromine, X is not p-toluoyl; and a process for the preparation thereof.

  公式（I）的化合物，其中R1是氢或羟基保护基；R2和R3相同或不同，且独立地选择自卤素或—O—SO2—X；其中X是—C1-C4烷基；C1-C4烷基被一个或多个卤素取代；或被取代或未取代的苯基，其中所述苯基取代基被选择自卤素、硝基和C1-C4烷基；但当R3为溴时，X不是对甲苯基；以及其制备方法。