(+/-)-(1S,2R)-1,2-dihydro-2-(4-bromophenyl)-1-naphthol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-(1S,2R)-1,2-dihydro-2-(4-bromophenyl)-1-naphthol
• 英文别名: 2-(4-bromophenyl)-1,2-dihydronaphthalen-1-ol；(1S*2R*)-2-(4-bromophenyl)-1,2-dihydronaphthalen-1-ol；(1S,2R)-2-(4-bromophenyl)-1,2-dihydronaphthalen-1-ol
• 化学式: C₁₆H₁₃BrO
• 分子量: 301.183
• InChiKey: ZEGKYUMMXSZEHQ-HZPDHXFCSA-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-epoxy-1,4-dihydronaphthalene 、 钠盐 在 palladium diacetate 、 三环己基膦 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以69%的产率得到(+/-)-(1S,2R)-1,2-dihydro-2-(4-bromophenyl)-1-naphthol
  参考文献：
  名称：

  钯催化合成Oxabicyclic烯烃与Arylsulfinates钠-Stereocontrolled开环

  摘要：

  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。

  DOI：

  10.1021/acs.joc.6b00667

文献信息

• Palladium(II) Catalyst Systems for the Addition of Boronic Acids to Bicyclic Alkenes:  New Scope and Reactivity
  作者：Mark Lautens、Chris Dockendorff

  DOI：10.1021/ol035369i

  日期：2003.10.1

  [reaction: see text] The palladium-catalyzed ring-opening addition of arylboronic acids to heterobicyclic alkenes is reported. Excellent yields are obtained for the addition of a wide variety of arylboronic acids to aza- and oxabicyclic alkenes. This methodology is especially useful in the synthesis of 1-amino-2-aryldihydronaphthalene scaffolds, for which rhodium catalysts are currently unreactive

  [反应：见正文]据报道，钯催化将芳基硼酸开环加成到杂双环烯烃上。将多种芳基硼酸添加到氮杂和氧杂双环烯烃中可获得优异的收率。该方法在合成1-氨基-2-芳基二氢萘支架中特别有用，对于该支架来说，铑催化剂目前不具有反应性或得到复杂的混合物。这些反应的不对称形式正在开发中，并已报道了初步结果。
• Chromium-Catalyzed <i>syn</i>-Selective Ring-Opening Aryl-/Alkylation of 7-Oxabenzonorbornadiene Derivatives with Grignard Reagents
  作者：Kohei Nishi、Hayato Tsurugi、Kazushi Mashima

  DOI：10.1021/acscatal.2c05029

  日期：2023.3.3

  arylchromium species such as neutral triarylchromium(III) and anionic tetraarylchromate(III) suggested that in situ formed diarylchromate(I) from tetraarylchromate(III) served as the active species in this catalytic reaction. The magnetic susceptibility of the in situ generated chromium species from CrCl3(thf)3 and excess amounts of p-tolylmagnesium bromide was reasonable for the low-spin Cr(I) species (μ =

  三氯化铬与芳基/烷基格氏试剂在无配体条件下对7-氧苯并降冰片二烯衍生物的顺式选择性开环芳基/烷基化表现出极高的催化活性（转换数高达 2.4 × 10 4 ） ,以高产率生产syn -2-aryl/alkyl-1,2-dihydronaphthalen-1-ols。铬催化剂在开环芳基化条件下的优异催化活性使我们能够使用不稳定的芳基格氏试剂与酯和N-由相应的芳基碘化物和涡轮-格氏试剂合成的保护基团。阐明中性三芳基铬 (III) 和阴离子四芳基铬酸盐 (III) 等芳基铬物种反应性的对照实验表明，由四芳基铬酸盐 (III) 原位形成的二芳基铬酸盐 (I) 作为该催化反应中的活性物种。从 CrCl 3 (thf) 3原位生成的铬物质和过量的对甲苯基溴化镁的磁化率对于低自旋 Cr(I) 物质 (μ = 1.93 μ B ) 是合理的。
• 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.
• 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。