2,6-dimethyl-1,5-cyclooctanediol | 184044-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dimethyl-1,5-cyclooctanediol
• 英文别名: (1S,2S,5S,6S)-2,6-dimethylcyclooctane-1,5-diol
• CAS: 184044-85-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: PZIHHFKQTJPQQC-XKNYDFJKSA-N

物化性质

• 熔点：
  138 °C(Solv: 1,2-dichloroethane (107-06-2))
• 沸点：
  298.0±8.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  2,6-dimethyl-1,5-cyclooctanediol 在 吡啶 、 potassium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 27.5h， 生成 (1R,2S,5R,6S)-N-(1-naphthyl)-2,6-dimethyl-9-azabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Synthesis of New Chiral Amines, 2,6-Dimethyl-9-azabicyclo[3.3.1]nonane and Its Derivatives

  摘要：

  New chiral amines, 2,6-dimethyl-9-azabicyclo[3.3.1]nonane and its derivatives, were prepared starting from commercially available 1,5-dimethyl-1,5-cyclooctadiene followed by substitution reaction of the intermediate ditosylate with p-toluenesulfonamide under phase transfer conditions in 4 steps.

  DOI：

  10.3987/com-99-s71
• 作为产物：
  描述：

  1,5-dimethyl-1,5-cyclooctadiene 在 sodium tetrahydroborate 、 Lipase MY 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 194.0h， 生成 2,6-dimethyl-1,5-cyclooctanediol
  参考文献：
  名称：

  Synthesis of 2,6-dimethyl-9-aryl-9-phosphabicyclo[3.3.1]nonanes: their application to asymmetric synthesis of chiral tetrahydroquinolines and relatives

  摘要：

  Synthesis of 2,6-dimethyl-9-aryl-9-phosphabicyclo[3.3.1]nonanes from 1,5-cyclooctadiene and their application to asymmetric cyclization leading to chiral tetrahydroquinolines and relatives through palladium-catalyzed allylic alkylation are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.078

文献信息

• New monodentate chiral phosphine 2,6-dimethyl-9-phenyl-9-phosphabicyclo[3.3.1]nonane(9-PBN): Application to asymmetric allylic substitution reaction
  作者：Yasumasa Hamada、Noriko Seto、Hiroki Ohmori、Keiichiro Hatano

  DOI：10.1016/0040-4039(96)01718-2

  日期：1996.10

  New monodentate chiral phosphines, (+)- and (−)-2,6-dimethyl-9-phenyl-9-phosphabicyclo[3.3.1]nonanes ((+)- and (−)-9-PBNs), were prepared from 1,5-dimethyl-1,5-cyclooctadiene, and their application to the asymmetric allylic substitution reaction proved the utility of 9-PBNs as chiral phosphine ligands.

  制备了新的单齿手性膦，（+）-和（-）-2,6-二甲基-9-苯基-9-磷酸双环[3.3.1]壬烷（（+）-和（-）-9-PBNs）。 1,5-二甲基-1,5-环辛二烯的合成及其在不对称烯丙基取代反应中的应用证明了9-PBN作为手性膦配体的实用性。
• C2-Symmetric nitroxides and their potential as enantioselective oxidants
  作者：Benjamin Graetz、Scott Rychnovsky、Wen-Hao Leu、Patrick Farmer、Rong Lin

  DOI：10.1016/j.tetasy.2005.09.016

  日期：2005.10

  The synthesis and evaluation of four C-2-symmetric nitroxides are presented. The nitroxides were evaluated for their ability to mediate the oxidation of several alcohols and found to have good catalytic activity. One enantioenriched nitroxide was found to kinetically resolve selected secondary alcohols with very modest selectivities. (c) 2005 Elsevier Ltd. All rights reserved.