2,6-dimethyl-1,5-cyclooctanediol | 944467-27-0

• 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: 2,6-dimethylcyclooctane-1,5-diol
• CAS: 944467-27-0
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: PZIHHFKQTJPQQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-1,5-cyclooctanediol 在 吡啶 、 Lipase MY 作用下， 以 正庚烷 为溶剂， 反应 192.0h， 生成 (1S,2S,5S,6S)-1,5-bis(p-toluenesulfonyloxy)-2,6-dimethylcyclooctane
  参考文献：
  名称：

  新型单齿手性膦2,6-二甲基-9-苯基-9-磷酸双环[3.3.1]壬烷（9-PBN）：在不对称烯丙基取代反应中的应用

  摘要：

  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。

  DOI：

  10.1016/0040-4039(96)01718-2
• 作为产物：
  描述：

  1,5-dimethyl-1,5-cyclooctadiene 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 以55%的产率得到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.
• Synthesis of 2,6-dimethyl-9-aryl-9-phosphabicyclo[3.3.1]nonanes: their application to asymmetric synthesis of chiral tetrahydroquinolines and relatives
  作者：Osamu Hara、Tomoaki Koshizawa、Kazuishi Makino、Iyo Kunimune、Atsushi Namiki、Yasumasa Hamada

  DOI：10.1016/j.tet.2007.03.078

  日期：2007.7

  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.