(1R,2S)-2-(3-chlorophenyl)-1,2-dihydronaphthalen-1-ol | 1092115-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-2-(3-chlorophenyl)-1,2-dihydronaphthalen-1-ol
• CAS: 1092115-03-1
• 化学式: C₁₆H₁₃ClO
• 分子量: 256.732
• InChiKey: XRTCZQFTKCCIFA-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,4-二氢-1,4-环氧萘 、 3-氯苯硼酸 在 C₃₄H₂₅O₂PPd 、 caesium carbonate 作用下， 以 氯仿 、 水 为溶剂， 生成 (1S*2R*)-2-(3-chlorophenyl)-1,2-dihydronaphthalen-1-ol 、 (1R,2S)-2-(3-chlorophenyl)-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  含P的Palladacycles催化氧杂双环烯烃与芳基硼酸的不对称开环反应。

  摘要：

  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。

  DOI：

  10.1021/ol801294b

文献信息

• Platinum(II)-Catalyzed Asymmetric Ring-Opening Addition of Arylboronic Acids to Oxabenzonorbornadienes
  作者：Xuejing Pan、Guobao Huang、Yuhua Long、Xiongjun Zuo、Xuan Xu、Fenglong Gu、Dingqiao Yang

  DOI：10.1021/jo402386k

  日期：2014.1.3

  A new platinum(II)-catalyzed asymmetric ring-opening addition of arylboronic acids to oxabenzonorbornadienes was developed, which afforded the corresponding cis-2-aryl-1,2-dihydronaphthalen-1-ol products in high yields (up to 97%) with moderate to good enantioselectivities (up to 89% ee) under very mild conditions. The effects of various ligands, catalyst loading, bases, solvents, and temperatures on the yield and enantioselectivity of the reaction were also investigated. The cis configuration of product 2m was confirmed by X-ray diffraction analysis. A potential mechanism for the present catalytic reaction is proposed.
• 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.