(1R,2S)-2-(2-chlorophenyl)-1,2-dihydronaphthalen-1-ol | 1403608-44-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-2-(2-chlorophenyl)-1,2-dihydronaphthalen-1-ol
• CAS: 1403608-44-5
• 化学式: C₁₆H₁₃ClO
• 分子量: 256.732
• InChiKey: NWFZXPPDWSVIBT-HOCLYGCPSA-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

• 作为反应物：
  描述：

  (1R,2S)-2-(2-chlorophenyl)-1,2-dihydronaphthalen-1-ol 在 palladium diacetate 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.5h， 以31 mg的产率得到(6aS,11aR)-6a,11a-dihydronaphtho[1,2-b]benzofuran
  参考文献：
  名称：

  Rh / Pd催化一锅法合成手性二氢苯并呋喃骨架

  摘要：

  描述了手性二氢苯并呋喃骨架的一锅合成。该方法利用Rh催化的不对称开环（ARO）和Pd催化的C–O偶联，以优异的对映选择性提供了产品，而无需分离中间体。进行了系统的金属-配体研究，以产物对映体纯度为指标，研究了每个催化体系的相容性。

  DOI：

  10.1021/ol302646a
• 作为产物：
  描述：

  2-(2-chlorophenyl)-1,3,2-dioxaborolane 、 1,4-二氢-1,4-环氧萘 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (S,R)-PPF-P(t-Bu)2 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以74%的产率得到(1R,2S)-2-(2-chlorophenyl)-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  Rh / Pd催化一锅法合成手性二氢苯并呋喃骨架

  摘要：

  描述了手性二氢苯并呋喃骨架的一锅合成。该方法利用Rh催化的不对称开环（ARO）和Pd催化的C–O偶联，以优异的对映选择性提供了产品，而无需分离中间体。进行了系统的金属-配体研究，以产物对映体纯度为指标，研究了每个催化体系的相容性。

  DOI：

  10.1021/ol302646a

文献信息

• 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 。
• 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.