(1R,5R,6S)-6-hydroxybicyclo[3.3.1]nonane-2-one | 84847-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5R,6S)-6-hydroxybicyclo[3.3.1]nonane-2-one
• 英文别名: (1R,5R,6S)-6-hydroxybicyclo[3.3.1]nonan-2-one
• CAS: 84847-97-2
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: FDRXGHNSOQDZAH-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5R,6S)-6-hydroxybicyclo[3.3.1]nonane-2-one 、 4-硝基苯肼 以53%的产率得到
  参考文献：
  名称：

  KADZYAUSKAS P. P.; BUTKUS EH. P.; VASYULITE YU. A.; AVERINA N. V.; ZEFIRO+, XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 3, 315-318

  摘要：

  DOI：
• 作为产物：
  描述：

  Bicyclo<3.3.1>nonan-2,6-diol 生成 (1R,5R,6S)-6-hydroxybicyclo[3.3.1]nonane-2-one
  参考文献：
  名称：

  KADZYAUSKAS P. P.; BUTKUS EH. P.; VASYULITE YU. A.; AVERINA N. V.; ZEFIRO+, XIMIYA GETEROTSIKL. SOEDIN., 1979, HO 3, 315-318

  摘要：

  DOI：

文献信息

• Intramolecular reactions involving positions C(2), C(6) and (C2), C(7) in the bicyclo[3.3.1]nonane ring system
  作者：Roger Bishop、William Parker、James Ronald Stevenson

  DOI：10.1039/p19810000565

  日期：——

  Reactions likely to involve C(2)–C(6) and C(2)–C(7) intramolecular reactions in bicyclo[3.3.1]nonane derivatives are discussed in terms of the conformations available to the ring system. While endo-6-hydroxybicyclo[3.3.1]-nonan-2-one (11) incorporated three deuterium atoms (excluding the hydroxy-group) on heating with NaOD, the exo-isomer (17) exchanged the six hydrogens adjacent to the oxygenation

  关于双环[3.3.1]壬烷衍生物中可能涉及C（2）–C（6）和C（2）–C（7）分子内反应的反应，根据环系统可用的构象进行了讨论。虽然内与NaOD加热-6-羟基双环[3.3.1] -nonan -2-酮（11）引入的三种氘原子（不包括羟基基团）时，外异构体（17）交换邻近六个氢氧合功能但不具有羰基质子。证据表明，立体定向碱基诱导的2,6-氢化物迁移很可能是通过双扭转船的过渡状态。用HCl水溶液在丙酮中处理6，6-乙二氧基-2-甲氧基亚甲基双环-[3.3.1]壬烷（36）以高收率产生2-羟基原金刚烷-10-酮（38）。该过程是由于含氧基团的水解而产生的，从而释放出内部的酮醛中间体（37），该中间体随后在C（2）醛与C（7）之间进行了分子内羟醛缩合。
• Ein rascher zugang zu optisch aktiven adamantan-derivaten
  作者：Gerhard Hoffmann、Rainer Wiartalla

  DOI：10.1016/s0040-4039(00)87734-5

  日期：——
• Stereoselective bioreduction for the resolution of racemic mixtures of bicyclo[3.3.1]nonane-2,6-dione using vegetables
  作者：Albinas Zilinskas、Jolanta Sereikaite

  DOI：10.1016/j.molcatb.2013.01.022

  日期：2013.6

  Screening of various vegetables as biocatalysts for the stereoselective bioreduction and resolution of racemic bicyclo[3.3.1]nonane-2,6-dione was performed. Vegetables of the family Apiaceae, i.e. the roots of parsnip (Pastinaca sativa), celery (Apium graveolens), parsley (Petroselinum crispum) and carrot (Daucus carota) were found to be the best. The methodology described here allows the efficient enantioseparation of (+)-enantiomer of bicyclo[3.3.1]nonane-2,6-dione. The reaction time, temperature and the amount of celery roots were optimized and (+)-enantiomer was obtained with the optical purity of 90-98% and the yield of more than 90%. (C) 2013 Elsevier B.V. All rights reserved.