(-)-(1R,2S,5R,6S)-bicyclo<3.3.1>nonane-2,6-diol | 69575-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(1R,2S,5R,6S)-bicyclo<3.3.1>nonane-2,6-diol
• 英文别名: (-)-(1R,2S,5R,6S)-Bicyclo<3.3.1>nonan-2,6-diol；(1R,2S,5R,6S)-bicyclo[3.3.1]nonane-2,6-diol
• CAS: 69575-87-7
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: ZAFAKOTZLSQTTI-HXFLIBJXSA-N

物化性质

• 沸点：
  294.8±8.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-(1R,2S,5R,6S)-bicyclo<3.3.1>nonane-2,6-diol 在 chromium(VI) oxide 、 氢氧化钾 、 硫酸 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 (S,S)-bicyclo[3.3.1]nonane-2,6-dione
  参考文献：
  名称：

  竞争性物质和绝对免疫性2，6-二取代双环[3.3.1] nonanen

  摘要：

  2,6-二取代双环[3.3.1]壬烷的绝对构型的拆分和测定

  DOI：

  10.1002/hlca.19780610804
• 作为产物：
  描述：

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

  Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation

  摘要：

  Lipase QL (from Alcaligenes sp.)-catalyzed acylation of alcohols using isopropenyl acetate as the acylating agent in diisopropyl ether converted preferentially primary alcohols with an S configuration and secondary alcohols with an R configuration into the corresponding homochiral acetates. On the basis of observed enantiomer selectivities, a predictive active site model for lipase QL is proposed for identifying which enantiomer of a primary or a secondary alcohol reacts faster in this acylation. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00429-6

文献信息

• Lipase YS-Catalyzed Enantioselective Transesterification of Alcohols of Bicarbocyclic Compounds
  作者：Koichiro Naemura、Hirotsugu Ida、Ritsuko Fukuda

  DOI：10.1246/bcsj.66.573

  日期：1993.2

  Lipase YS-catalyzed enantioselective acylations of (1RS, 2RS, 4RS, 5RS)-bicyclo[2.2.1]heptane-2,5-diol, (1RS, 2SR, 4RS, 5SR)-bicyclo[2.2.2]octane-2,5-diol, (1RS, 2RS, 4RS, 5RS)-bicyclo[2.2.2]octane-2,5-diol, and (1RS, 2SR, 5RS, 6SR)-bicyclo[3.3.1]nonane-2,6-diol with aryl acetates such as phenyl acetate, 1-naphthyl acetate, and 2-naphthyl acetate gave the monoacetates and the diols in optically active

  脂肪酶 YS 催化的 (1RS, 2RS, 4RS, 5RS)-bicyclo[2.2.1]heptane-2,5-diol, (1RS, 2SR, 4RS, 5SR)-bicyclo[2.2.2]octane-2 的对映选择性酰化,5-二醇、(1RS、2RS、4RS、5RS)-双环[2.2.2]辛烷-2,5-二醇和(1RS、2SR、5RS、6SR)-双环[3.3.1]壬烷-2， 6-二醇与乙酸芳基酯如乙酸苯酯、乙酸1-萘酯和乙酸2-萘酯得到单乙酸酯和旋光形式的二醇。(+)-(2R, 5R)-2-乙酰氧基双环[2.2.1]庚烷-5-醇，(-)-(1S, 2R, 4S, 5R)-2-乙酰氧基双环[2.2.2]的光学纯度使用乙酸苯酯获得的辛烷-5-醇和 (+)-(2R, 6R)-2-乙酰氧基双环[3.3.1]壬烷-6-醇高于已通过 PLE 催化水解拆分的单乙酸酯相应的外消旋二乙酸酯。使用苯酯如
• Facile Preparation of Optically Active Bicyclo[3.3.1]nonane-2,6-diol and 3,3,7,7-Tetramethylbicyclo[3.3.1]nonane-2,6-diol by Enzyme-Catalyzed Hydrolysis, and Enantiomer Recognition Behavior of Crown Ethers and Podands Having These Diols as a Chiral Subunit
  作者：Koichiro Naemura、Takahisa Matsumura、Masanori Komatsu、Yoshiki Hirose、Hiroaki Chikamatsu

  DOI：10.1246/bcsj.62.3523

  日期：1989.11

  with 86% e.e. By lithium aluminum hydride reduction, (+)-4 and (−)-5 were converted to (+)-bicyclo[3.3.1]nonane-2,6-diol (3) and (−)-3 with high optical purity, respectively, and (+)-7 was obtained from (+)-9. Using these optically active diols 3 and 7 as a chiral subunit, optically active crown ethers and podands were prepared and their enantiomer recognition behavior was evaluated by the enantiomer

  使用来自圆柱假丝酵母的脂肪酶水解 2,6-二乙酰氧基双环 [3.3.1] 壬烷 (5) 得到 (+)-(1S,2R,5S,6R)-6-乙酰氧基双环 [3.3.1]nonan-2-ol ( 4) 具有 81% ee 和 (-)-(1R,2S,5R,6S)-5 具有 95% ee，以及猪肝酯酶催化的 2,6-二乙酰氧基-3,3,7,7-四甲基双环水解[3.3.1]壬烷 (9) 得到 (-)-(1S,2R,5S,6R)-3,3,7,7-四甲基双环 [3.3.1] 壬烷-2,6-二醇 (7)，其中 96 %ee和(+)-(1R,2S,5R,6S)-9与86%ee 通过氢化铝锂还原，(+)-4和(-)-5转化为(+)-双环[3.3。 1]壬烷-2,6-二醇 (3) 和 (-)-3 分别具有高光学纯度，(+)-7 由 (+)-9 获得。使用这些光学活性二醇 3 和 7 作为手性亚基，
• Enzymatic hydrolysis of 2,6-diacetoxybicyclo[3.3.1]nonane and 2,6-diacetoxy-3,3,7,7-tetramethylbicyclo[3.3.1]nonane; a facile synthesis of the optically active chiral subunit for crown ethers
  作者：Koichiro Naemura、Takahisa Matsumura、Masanori Komatsu、Yoshiki Hirose、Hiroaki Chikamatsu

  DOI：10.1039/c39880000239

  日期：——

  Hydrolysis of 2,6-diacetoxybicyclo[3.3.1]nonane (5) using lipase from Candida cylindracea gave (+)-(1S,2R,5S,6R)-(4)[81% enantiomeric excess (e.e.)] and (–)-(1R,2S,5R,6S)-(5)[95% e.e.], and pig liver esterase-catalysed hydrolysis of 2,6-diacetoxy-3,3,7,7-tetramethylbicyclo[3.3.1]nonane (9) gave (–)-(1S,2R,5S,6R)-(7)(96% e.e.) and (+)-(1R,2S,5R,6S)-(9)(86% e.e.); the enantiomer recognition behaviour

  使用来自假丝酵母的脂肪酶水解2,6-二乙酰氧基双环[3.3.1]壬烷（5）得到（+）-（1 S，2 R，5 S，6 R）-（4）[81％对映体过量（ee ）]和（–）-（1 R，2 S，5 R，6 S）-（5）[95％ee]，以及猪肝酯酶催化的2,6-二乙酰氧基-3,3,7的水解， 7-四甲基双环[3.3.1]壬烷（9）得到（–）-（1 S，2 R，5 S，6 R）-（7）（96％ee）和（+）-（1 R，2S，5 R，6 S）-（9）（86％ee）; 分别研究了由（-）-（3）和（+）-（7）制得的冠醚（-）-（11）和（+）-（12）的对映体识别行为。
• Crystallisation of C2-symmetric endo,endo-bicyclo[3.3.1]nonane-2-6-diols: supramolecular synthons and concomitant degrees of enantiomer separation
  作者：Vi T. Nguyen、Isa Y. H. Chan、Roger Bishop、Donald C. Craig、Marcia L. Scudder

  DOI：10.1039/b900463g

  日期：——

  Each of the three racemic C2-symmetric endo,endo-bicyclo[3.3.1]nonane-2,6-diols 6–8 shows a dominant, but different, mode of crystallisation across a wide range of solvents. These outcomes depend on the type of supramolecular synthon employed and the resulting degree of enantiomer separation that takes place. Diol 6 utilises the centrosymmetric hydrogen bonded (O–H)6 cycle and forms racemic crystals

  三种外消旋的C 2对称内消旋，内双环[3.3.1]壬烷-2,6-二醇6-8均在多种溶剂中均显示出主要但不同的结晶方式。这些结果取决于所采用的超分子合成子的类型以及所产生的对映异构体分离程度。二醇6利用中心对称氢键（OH）6循环形成含有两种对映体紧密混合的外消旋晶体。相反，二醇7使用（OH）4周期形成同手性层，但由于相邻层具有相反的旋向性，因此仍会产生外消旋晶体。二元醇8通过使用交联的（OH）8重复螺旋形成氢键网络，并且自分离产生纯的（+）-和纯的（-）晶体（聚结）的混合物。由于团聚物可以分离成它们的纯对映异构体，因此后一个发现为获得手性纯的双环[3.3.1]壬烷化合物提供了一种新的制备方法，该化合物在有机合成中具有价值。
• Enantioselective acylation of alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify the faster reacting enantiomer of an alcohol in this acylation
  作者：Koichiro Naemura、Masaki Murata、Rie Tanaka、Masashi Yano、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/0957-4166(96)00186-3

  日期：1996.6

  Lipase QL-catalyzed acylation of secondary alcohols using isopropenyl acetate as the acylating agent in diisopropyl ether gave preferentially the corresponding acetate with an R configuration. On the basis of the results, a predictive active site model for lipase QL is proposed for identifying which enantiomer of a secondary alcohol reacts faster in this reaction. (C) 1996 Elsevier Science Ltd