rac-trans-2-(2-methoxyphenyl)cyclopentanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: rac-trans-2-(2-methoxyphenyl)cyclopentanol
• 英文别名: trans-2-(2-Methoxyphenyl)cyclopentanol；(1R,2S)-2-(2-methoxyphenyl)cyclopentan-1-ol
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: VKPWQSCURHLAGT-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  rac-trans-2-(2-methoxyphenyl)cyclopentanol 在 偶氮二甲酸二异丙酯 、 3,5-二硝基苯甲酸 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-甲氧基苯基)环戊醇
  参考文献：
  名称：

  Palladium-catalyzed reaction of 4-cyclopentene-1,3-diol monoacetate with Grignard reagents producing hitherto unreachable cis-1,2-isomersElectronic supplementary information (ESI) available: typical procedure for the palladium-catalyzed reaction, determination of the structures and spectral data of products. See http://www.rsc.org/suppdata/cc/b3/b316596e/

  摘要：

  在钯催化剂存在下，4-环戊烯-1,3-二醇单乙酸酯与 RMgCl（R = 烷基、芳基）的反应在保留构型的情况下进行，主要产物为顺式-1,2-中间体异构体。

  DOI：

  10.1039/b316596e
• 作为产物：
  描述：

  (1S,5R)-6-Oxa-bicyclo[3.1.0]hexane 、 苯甲醚 在 正丁基锂 、 四甲基乙二胺 、 三氟化硼乙醚 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以99%的产率得到rac-trans-2-(2-methoxyphenyl)cyclopentanol
  参考文献：
  名称：

  Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF3·OEt2

  摘要：

  It is presented that a number of o-2-hydroxyalkylanisoles could be efficiently synthesized through the regioselective ring-opening reaction of epoxides with o-lithioanisoles in the presence of BF3 center dot OEt2 Lewis-acid catalyst. Sterically demanding o-lithioanisoles had to be generated by exploiting the combination of (BuLi)-Bu-n and a catalytic amount of TMEDA (0.20 equiv) in Et2O as the lithiator whereas 'normal' anisole could be lithiated at ortho-position by treatment with (BuLi)-Bu-n in THE as usual. Surprisingly, the availability of THE and a catalytic amount of TMEDA (0.20 equiv) in the reaction mixture was found to enhance the reaction yields dramatically. A complex aggregate formation by the co-operative ligation of THF and TMEDA to ortho-lithioanisole(s) was proposed to rationalize the high reactivity achieved in the ring-opening reaction of epoxides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.116

文献信息

• Enantioselective Cross-Coupling of <i>meso</i>-Epoxides with Aryl Halides
  作者：Yang Zhao、Daniel J. Weix

  DOI：10.1021/jacs.5b01909

  日期：2015.3.11

  The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78–95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal

  首次提出了芳基溴化物与内消旋环氧化物形成反式-β-芳基环烷醇的对映选择性交叉亲电偶联。该反应由(bpy)NiCl 2 和手性二茂钛在还原条件下的组合催化。产率范围为 57% 至 99%，对映体过量为 78-95%。这 30 个例子包括各种官能团（醚、酯、酮、腈、缩酮、三氟甲基、磺酰胺、磺酸酯）、芳基和乙烯基卤化物以及五至七元环。一氧化环辛烯向芳基[3.3.0]双环辛醇的转化强烈暗示了碳自由基的中介作用。