(1R,2S)-6,7-dimethoxy-2-methyl-1,2-dihydronaphthalen-1-ol | 1169869-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-6,7-dimethoxy-2-methyl-1,2-dihydronaphthalen-1-ol
• CAS: 1169869-73-1
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: SMZLDHBSHNUDGQ-ISVAXAHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基铝 、 1,4-dihydro-6,7-dimethoxy-1,4-epoxynaphthalene 在 噻吩-2-甲酸亚铜(I) 、 1,1-diphenyl-N,N-bis((S)-1-phenylethyl)phosphinamine 作用下， 以 light petroleum 、 甲基叔丁基醚 为溶剂， 反应 20.0h， 生成 (1R,2S)-6,7-dimethoxy-2-methyl-1,2-dihydronaphthalen-1-ol 、 (1S,2R)-6,7-dimethoxy-2-methyl-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  Copper-catalyzed desymmetrization of oxabenzonorbornadienes with aluminum reagents

  摘要：

  The desymmetrization of oxabenzonorbornadienes with aluminum reagents and SimplePhos as chiral ligand is described. The corresponding homoallylic alcohols are obtained in high yield, diastereoselectivity, and enantiomeric excess. Furthermore the first anti enantioselective desymmetrization with aromatic nucleophiles is reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.219

文献信息

• Platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with Grignard reagents
  作者：Dingqiao Yang、Ni Liang

  DOI：10.1039/c3ob42199f

  日期：——

  A new platinum-catalyzed anti-stereocontrolled ring-opening of oxabicyclic alkenes with various Grignard reagents was reported, which afforded the corresponding anti-2-substituted-1,2-dihydronaphthalen-1-ol products with moderate to good yields in the presence of a catalytic amount of Pt(PPh3)4 (2.5 mol%) under mild conditions. The effects of catalyst loading, solvent and temperature on the yield were

  报道了一种新的铂催化的各种格氏试剂对氧杂双环烯烃的反立体控制开环，在存在丁二酮的情况下提供了中等至良好收率的相应的抗-2-取代-1,2-二氢萘-1-醇产物。在温和条件下催化量的Pt（PPh 3）4（2.5 mol％）。还研究了催化剂用量，溶剂和温度对产率的影响。此外，通过X射线衍射分析确认了产物5i的反式构型。
• Copper-Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Grignard and Aluminum Reagents
  作者：Alexandre Alexakis、Renaud Millet、Ludovic Gremaud、Tania Bernardez、Laëtitia Palais

  DOI：10.1055/s-0029-1216838

  日期：2009.6

  A highly enantioselective method for the copper-catalyzed desymmetrization of oxabenzonorbornadienes with aluminum reagents and SimplePhos as chiral ligand has been developed. The same reaction with Grignard reagents is also reported. A wide range of alkyl chains have been used with moderate to high enantio­selectivity and high trans selectivity. The transfer of a methyl group is also reported with

  已经开发了一种高度对映选择性的方法，该方法通过铝试剂和SimplePhos作为手性配体，对铜进行草酰苯并降冰片二烯的脱对称反应。还报道了与格氏试剂的相同反应。广泛使用的烷基链具有中等至高对映选择性和高反式选择性。还报道了甲基的转移，其对映体和非对映体过量，并且对于不同的底物，产率很高。最后，我们已经能够执行第一跨与芳基oxabenzonorbornadienes的对映选择性desymmetrization。 铜催化-不对称转化-格氏试剂-铝试剂-SimplePhos
• Copper-catalyzed desymmetrization of oxabenzonorbornadienes with aluminum reagents
  作者：Renaud Millet、Tania Bernardez、Laëtitia Palais、Alexandre Alexakis

  DOI：10.1016/j.tetlet.2009.02.219

  日期：2009.7

  The desymmetrization of oxabenzonorbornadienes with aluminum reagents and SimplePhos as chiral ligand is described. The corresponding homoallylic alcohols are obtained in high yield, diastereoselectivity, and enantiomeric excess. Furthermore the first anti enantioselective desymmetrization with aromatic nucleophiles is reported. (C) 2009 Elsevier Ltd. All rights reserved.