2-(4-(trifluoromethyl)phenyl)-1,2-dihydronaphthalen-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-(trifluoromethyl)phenyl)-1,2-dihydronaphthalen-1-ol
• 英文别名: (1S,2R)-2-[4-(trifluoromethyl)phenyl]-1,2-dihydronaphthalen-1-ol
• 化学式: C₁₇H₁₃F₃O
• 分子量: 290.285
• InChiKey: PQNWEFPXBCPGJM-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-(trifluoromethyl)phenyl)-1,2-dihydronaphthalen-1-ol 在 C₃₆H₃₅F₃NO₃Pd 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以55%的产率得到2-(4-(trifluoromethyl)phenyl)naphthalene
  参考文献：
  名称：

  Palladacycle-Catalyzed Highly Efficient Kinetic Resolution of 1-Hydroxy-2-aryl-1,2-dihydronaphthalenes via Dehydration Reaction

  摘要：

  Palladacycles showed their high efficiency in the kinetic resolution of 1-hydroxy-2-aryl-1,2-dihydronaphthalenes via dehydration, providing optically active products in high yields and high ee with an S factor up to 26. The superiority of a benzylic-substituted palladacycle in asymmetric induction was also demonstrated.

  DOI：

  10.1021/ol801946e
• 作为产物：
  描述：

  1,4-二氢-1,4-环氧萘 、 4-三氟甲基苯硼酸新戊二醇酯 在 1,2-双(二苯基膦基)苯 、 copper(l) chloride 、 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以41%的产率得到2-(4-(trifluoromethyl)phenyl)-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  铜催化氧杂双环烯烃与有机硼试剂的顺式选择性开环交叉偶联

  摘要：

  在Cu（我） -催化的开环的oxabicyclic烯烃的交叉偶联与有机硼试剂提供访问顺-2-芳基-1,2-二氢萘-1-醇衍生物，在对比的独家反式-选择性在与格氏试剂的铜催化反应。DFT计算表明，反应可能是通过硼酸酯副产物辅助的开环反应进行的，这是速率确定步骤中β-氧经典消除的替代途径。

  DOI：

  10.1039/d0ob02557g

文献信息

• Palladium-Catalyzed <i>syn</i>-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates
  作者：Yue Li、Wen Yang、Guo Cheng、Dingqiao Yang

  DOI：10.1021/acs.joc.6b00667

  日期：2016.6.3

  Palladium-catalyzed syn-stereocontrolled ring-opening reactions of oxabenzonorbornadienes with a wide range of sodium arylsulfinates were investigated, affording the desired products in good to excellent yields under an air atmosphere. This protocol provides a low-cost new viable and convenient method toward the synthesis of cis-2-aryl-1,2-dihydronaphthalen-1-ol with good functional group tolerance

  研究了氧杂苯并降冰片二烯与各种芳基亚磺酸钠的钯催化的顺式-立体控制的开环反应，在空气气氛下以良好或优异的收率提供了所需的产物。该方案为合成具有良好官能团耐受性的顺式-2-芳基-1,2-二氢萘-1-醇提供了一种低成本，可行且方便的新方法。另外，通过X射线衍射分析确定了3da的顺式构型，并提出了可能的开环反应机理。
• Asymmetric Ring-Opening Reaction of Oxabicyclic Alkenes with Aryl Boronic Acids Catalyzed by P-Containing Palladacycles
  作者：Ting-Ke Zhang、Dong-Liang Mo、Li-Xin Dai、Xue-Long Hou

  DOI：10.1021/ol801294b

  日期：2008.9.1

  The chiral phosphine-containing palladacycle, synthesized easily from H-MOP, showed its high catalytic activity as well as asymmetric induction ability in ring-opening reaction of oxabicyclic alkenes with arylboronic acids, providing corresponding products in high yields and high ee.

  由H-MOP容易合成的含手性膦的palladacycle在氧杂双环烯烃与芳基硼酸的开环反应中显示出高催化活性和不对称诱导能力，从而以高收率和高ee提供相应的产物。
• Nickel-Catalyzed Asymmetric Ring Opening of Oxabenzonorbornadienes with Arylboronic Acids
  作者：Zhongyi Zeng、Dingqiao Yang、Yuhua Long、Xuejing Pan、Guobao Huang、Xiongjun Zuo、Wen Zhou

  DOI：10.1021/jo500821m

  日期：2014.6.6

  A new, versatile, and highly efficient nickel-catalyzed asymmetric ring-opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of arylboronic acids has been developed, yielding cis-2-aryl-1,2-dihydronaphthalen-1-ols in high yields (up to 99%) with good to excellent enantioselectivities (up to 99% ee) under very mild conditions. The effects of various nickel precursors, chiral bidentate ligands, catalyst loadings, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. A plausible mechanism was proposed to account for the formation of the corresponding cis-ring-opened products based on the X-ray structure of product 4b.
• Cu-Catalyzed <i>cis</i>-selective ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent
  作者：Bowen Liu、Guochun Peng、Yu Zhang、Chunhui Liu、Jinbo Zhao

  DOI：10.1039/d0ob02557g

  日期：——

  The Cu(I)-catalyzed ring-opening cross-coupling of an oxabicyclic olefin with an organoboron reagent provides access to cis-2-aryl-1,2-dihydronaphthalen-1-ol derivatives, in contrast to the exclusive trans-selectivity in related Cu-catalyzed reactions with Grignard reagents. DFT calculations suggest that the reaction possibly proceeds via boronic ester by-product assisted ring-opening as an alternative

  在Cu（我） -催化的开环的oxabicyclic烯烃的交叉偶联与有机硼试剂提供访问顺-2-芳基-1,2-二氢萘-1-醇衍生物，在对比的独家反式-选择性在与格氏试剂的铜催化反应。DFT计算表明，反应可能是通过硼酸酯副产物辅助的开环反应进行的，这是速率确定步骤中β-氧经典消除的替代途径。
• Palladacycle-Catalyzed Highly Efficient Kinetic Resolution of 1-Hydroxy-2-aryl-1,2-dihydronaphthalenes via Dehydration Reaction
  作者：Ting-Ke Zhang、Dong-Liang Mo、Li-Xin Dai、Xue-Long Hou

  DOI：10.1021/ol801946e

  日期：2008.12.4

  Palladacycles showed their high efficiency in the kinetic resolution of 1-hydroxy-2-aryl-1,2-dihydronaphthalenes via dehydration, providing optically active products in high yields and high ee with an S factor up to 26. The superiority of a benzylic-substituted palladacycle in asymmetric induction was also demonstrated.