(1S,2R)-5,8-dimethoxy-2-phenyl-1,2-dihydronaphthalen-1-ol | 1088963-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2R)-5,8-dimethoxy-2-phenyl-1,2-dihydronaphthalen-1-ol
• 英文别名: cis-5,8-dimethoxy-2-phenyl-1,2-dihydronaphthalen-1-ol
• CAS: 1088963-91-0
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: FQEVOVROSPJCHV-ACJLOTCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1,4-dihydro-5,8-dimethoxy-1,4-epoxynaphthalene 、 苯硼酸 在 C₃₄H₂₅O₂PPd 、 caesium carbonate 作用下， 以 氯仿 、 水 为溶剂， 生成 (1R,2S)-5,8-dimethoxy-2-phenyl-1,2-dihydronaphthalen-1-ol 、 (1S,2R)-5,8-dimethoxy-2-phenyl-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

• 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。
• Water‐Promoted Palladium‐Catalyzed Asymmetric Ring‐Opening of Oxabenzonorbornadienes with Alkoxysilanes
  作者：Yun Tan、Yongqi Yao、Wen Yang、Qifu Lin、Guobao Huang、Minxiong Tan、Shuqi Chen、Donghan Chen、Dingqiao Yang

  DOI：10.1002/adsc.201901152

  日期：2020.1.7

  Water‐promoted palladium‐catalyzed asymmetric ring‐opening (ARO) reaction of oxabenzonorbornadienes with a wide variety of alkoxysilanes has been developed in a one‐pot fashion, yielding cis‐1,2‐dihydronaphthalen‐1‐ols in favourable yields (up to 98%) with gratifying enantioselectivities (up to 98% ee) under mild conditions. To the best of our knowledge, it represents the first example in the ring‐opening

  以单锅法开发了水促进的钯催化的草酰苯并降冰片二烯与多种烷氧基硅烷的不对称开环（ARO）反应，可产生有利的收率的顺式1,2-二氢萘-1-醇在温和条件下具有令人满意的对映选择性（最高98％ee）的98％）。据我们所知，它是氧杂双环烯烃与烷氧基硅烷开环反应的第一个例子。此外，通过X射线衍射分析确定了产物的顺式1,2-构型，并提出了目前催化开环反应的可能机理。
• 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.
• Chiral Palladacycle Catalysts Generated on a Single-Handed Helical Polymer Skeleton for Asymmetric Arylative Ring Opening of 1,4-Epoxy-1,4-dihydronaphthalene
  作者：Takeshi Yamamoto、Yuto Akai、Michinori Suginome

  DOI：10.1002/anie.201407358

  日期：2014.11.17

  Post‐polymerization CH activation of poly(quinoxaline‐2,3‐diyl)‐based helically chiral phosphine ligands (PQXphos) with palladium(II) acetate afforded chiral phosphapalladacycles quantitatively. In situ generated palladacycles exhibited enantioselectivities up to 94 % ee in the palladium‐catalyzed asymmetric ring‐opening arylation of 1,4‐epoxy‐1,4‐dihydronaphthalenes with arylboronic acids.

  聚合后Ç  ħ聚活化（喹喔啉-2,3-二基）基螺旋手性膦配体（PQXphos）与钯（II）醋酸盐，得到手性phosphapalladacycles定量。在钯催化的1,4-环氧-1,4-二氢萘与芳基硼酸的钯催化不对称开环芳基化反应中，原位生成的palladacycles表现出高达94％ee的对映选择性 。