2-hydroxy-6-(1-adamantyl)naphtalene | 37436-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-6-(1-adamantyl)naphtalene
• 英文别名: 6-(adamantan-1-yl)naphthalen-2-ol；6-(1-adamantyl)naphthalen-2-ol；6-(1-adamantyl)-2-naphthol；6-Adamantyl-(1)-2-hydroxy-naphthalin
• CAS: 37436-35-4
• 化学式: C₂₀H₂₂O
• mdl: MFCD19103279
• 分子量: 278.394
• InChiKey: XZRBITOOYQYBPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-hydroxy-6-(1-adamantyl)naphtalene 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 8-(adamantan-1-yl)-3-amino-1H-benzo[f]chromene-2-carbonitrile
  参考文献：
  名称：

  New synthesis of 3-amino-1H-benzo[f]chromene-2-carbonitriles

  摘要：

  3-Amino-1H-benzo[f]chromene-2-carbonitriles were synthesized by non-catalytic reaction from Mannich bases of the naphthalene series and malononitrile. Reactive 1-benzylidene(or methylidene)naphthalen-2(1H)-ones were presumed as intermediate products.

  DOI：

  10.1134/s1070428013030147
• 作为产物：
  描述：

  1-金刚烷醇 、 2-萘酚 在 三氟乙酸 作用下， 反应 12.0h， 以73%的产率得到2-hydroxy-6-(1-adamantyl)naphtalene
  参考文献：
  名称：

  Alkylation of aromatic compounds with adamantan-1-ol

  摘要：

  Reactions of substituted benzenes, naphthalenes, and 2- and 3-phenyl-1-benzofurans with adamantan-1-ol in trifluoroacetic acid lead to the formation of the corresponding mono-and diadamantylsubstituted aromatic compounds.

  DOI：

  10.1134/s1070428007040082

文献信息

• Methylation of Arenols through Ni-catalyzed C-O Activation with Methyl Magnesium Bromide
  作者：Wen-Juan Shi、Zhang-Jie Shi

  DOI：10.1002/cjoc.201700664

  日期：2018.3

  Direct alkylation of arenols with alkyl organometallic reagents has never been approached. Herein we reported the first successful example of nickel‐catalyzed methylation of arenols with methyl Grignard reagents to construct C(sp2)‐C(sp3) bond under mild conditions. The transformation was compatible with broad substrate scope of 2‐naphthol derivatives. Benzyl alcohol and biphenols were also suitable

  从未有过使用烷基有机金属试剂将芳烃直接烷基化的方法。在这里，我们报道了第一个成功的例子，该例子是在温和条件下用甲基格氏试剂进行镍催化的芳香烃甲基化，以构建C（sp 2）-C（sp 3）键。该转化与2-萘酚衍生物的广泛底物范围兼容。苄醇和联苯酚也是该甲基化的合适底物。
• Facile Approach for the Synthesis of 2,3,4,9-Tetrahydro-1<i>H</i>-xanthen-1-ones and 8,9,10,12-Tetrahydro-11<i>H</i>-benzo[<i>a</i>]xanthen-11-ones via Trapping of <i>o</i>-Quinone Methides
  作者：Vitaly A. Osyanin、Elena A. Ivleva、Yuri N. Klimochkin

  DOI：10.1080/00397911.2010.545164

  日期：2012.6.15

  Abstract An efficient, simple synthesis of 2,3,4,9-tetrahydro-1H-xanthene-1-ones and 8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-ones is reported by one-pot condensation of 3-dimethylamino-2-cyclohexen-1-ones with hydroxybenzyl alcohols, phenol, and 2-naphthol Mannich bases or their quaternized derivatives. The mechanism of the reaction is believed to involve the formation of the o-quinone methide

  摘要 2,3,4,9-四氢-1H-xanthene-1-ones 和 8,9,10,12-四氢-11H-benzo[a]xanthene-11-ones 的一种高效、简单的合成方法报道了- 3-二甲氨基-2-环己烯-1-酮与羟基苄醇、苯酚和2-萘酚曼尼希碱或其季铵化衍生物的锅缩合。据信该反应的机理涉及邻醌甲基化物中间体的形成。图形概要
• Fluorescent Quenching of the 2-Naphthoxide Anion by Aliphatic and Aromatic Halides. Mechanism and Consequences of Electron Transfer Reactions
  作者：Juan E. Argüello、Alicia B. Peñéñory

  DOI：10.1021/jo026518y

  日期：2003.3.1

  The fluorescent excited state of the 2-naphthoxide ion (1) is quenched by aliphatic and aromatic halides according to an electron-transfer mechanism, with generation of the corresponding alkyl and aryl radicals by a concerted or consecutive C-X bond fragmentation reaction. Whereas bromo- and iodobenzene follow a concerted ET mechanism (C-X, BDE control), 1-bromonaphthalene exhibits a stepwise process

  根据电子转移机理，脂族和芳族卤化物可淬灭2-萘氧基离子（1）的荧光激发态，并通过一致或连续的CX键断裂反应生成相应的烷基和芳基。溴和碘苯遵循一致的ET机理（CX，BDE控制），而1-溴萘则表现出逐步过程（πLUMO控制）。阴离子1与1-碘金刚烷（2）在DMSO中的光诱导反应在C3，C6和C8、1-金刚烷醇，1-金刚烷基2-萘醚和金刚烷上提供取代产物（3.2，13.2，12.2，2.8，2.5和分别为14.1％的收益）。在新戊基碘化物（3）与阴离子1的光化学反应中也观察到了复杂的混合物，该化合物在C1，C3，C6，C8和2-萘基新戊基醚（8.1、1.3、19.1，分别为31.1和2.8％）。在黑暗中不存在反应，并且由于存在自由基捕集剂二叔丁基硝基氧（DTBN）和1,4-环己二烯而抑制了光诱导反应，这是这些取代的自由基链机理的证据。另一方面，阴离子1与碘代苯（5）的光刺激反应仅达到C1偶联，得到41
• Practical Cross-Coupling between O-Based Electrophiles and Aryl Bromides via Ni Catalysis
  作者：Zhi-Chao Cao、Qin-Yu Luo、Zhang-Jie Shi

  DOI：10.1021/acs.orglett.6b02656

  日期：2016.12.2

  Cross-coupling of various O-based electrophiles with aryl bromides was developed through Ni-catalyzed C–O activation in the presence of magnesium. Beside carboxylates, carbamates, and ethers, phenols exhibited excellent reactivity under modified conditions. This chemistry was featured as a simple and environmentally benign process with low catalyst loading and easy manipulations. The method exhibited

  在镁的存在下，通过Ni催化的C–O活化，开发出了各种基于O的亲电试剂与芳基溴化物的交叉偶联反应。除羧酸盐，氨基甲酸酯和醚外，酚在改性条件下还具有出色的反应活性。该化学反应具有催化剂用量低，易于操作的简单，环保的特点。该方法展示了广泛的底物范围。
• Synthesis of benzo[f]coumarins from 2-trifluoroacetyl-1H-benzo[f]chromenes and 2-naphthols
  作者：Vitaly A. Osyanin、Dmitry V. Osipov、Yulia V. Popova、Irina A. Semenova、Yuri N. Klimochkin

  DOI：10.1007/s10593-017-2001-4

  日期：2016.12

  -ones containing the (2-hydroxy-1-naphthyl)methyl or 2-hydroxybenzyl substituent in position 2 was prepared by the reaction of 2-trifluoroacetyl-1H-benzo[f]chromenes with 2-naphthols in the presence of DBU. The reaction comprises 1,4-addition and intramolecular haloform type reaction followed by opening of the dihydropyran ring.

  通过2-三氟乙酰基-1 H-苯并[]的反应，制备了一系列在2位含有（2-羟基-1-萘基）甲基或2-羟基苄基取代基 的3 H-苯并[ f ]铬n- 3-3。在DBU存在下，带有2-萘酚的f ]色酮。该反应包括1，4-加成和分子内卤代型反应，然后打开二氢吡喃环。