1-[(2-羟基萘-1-基)-苯基甲基]萘-2-醇 | 29114-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-[(2-羟基萘-1-基)-苯基甲基]萘-2-醇
• 英文名称: benzylidene-1,1'-bis(2-naphthol)
• 英文别名: phenyl-bis-(2-hydroxy-1-naphthyl)methane；1,1'-(phenylmethylene)bis(naphthalen-2-ol)；1,1'-(Phenylmethylene)di(naphthalen-2-ol)；1-[(2-hydroxynaphthalen-1-yl)-phenylmethyl]naphthalen-2-ol
• CAS: 29114-24-7
• 化学式: C₂₇H₂₀O₂
• 分子量: 376.455
• InChiKey: WIPOIUBQFGBGSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(2-羟基萘-1-基)-苯基甲基]萘-2-醇 在 ytterbium(III) triflate [BPy]BF₄ 作用下， 以100%的产率得到14-phenyl-14H-dibenzo[a.j]xanthene
  参考文献：
  名称：

  Yb（OTf）3催化β-萘酚与醛在离子液体中的缩合反应：芳基14 H-二苯并[ a，j ]蒽的绿色合成

  摘要：

  在离子液体中，在tri三氟es存在下，通过一锅缩合β-萘酚和取代的苯甲醛，已经开发了一种简便，高效且绿色的芳基14 H-二苯并[ a，j ]蒽酮。

  DOI：

  10.1016/j.tetlet.2008.03.124
• 作为产物：
  描述：

  萘-2-酚钾 反应 8.0h， 生成 1-[(2-羟基萘-1-基)-苯基甲基]萘-2-醇
  参考文献：
  名称：

  Precursors in the alkylation of 2-naphthol with benzyl alcohol in the presence of a base

  摘要：

  DOI：

  10.1021/jo00223a039

文献信息

• Iron-based metal–organic framework, Fe(BTC): an effective dual-functional catalyst for oxidative cyclization of bisnaphthols and tandem synthesis of quinazolin-4(3H)-ones
  作者：Ali Reza Oveisi、Ahmad Khorramabadi-zad、Saba Daliran

  DOI：10.1039/c5ra19013d

  日期：——

  An iron-based metal–organic framework [Fe(BTC) (BTC: 1,3,5-benzenetricarboxylate)] has been shown to be an active and heterogeneous catalyst for both oxidative cyclization of methylenebisnaphthols and a modern tandem process (an in situ oxidation-aminal formation-oxidation sequence). Such a potential catalytic utility of Fe(BTC) makes it quite attractive for sustainable industrial chemistry.

  铁基金属-有机骨架[Fe（BTC）（BTC：1,3,5-苯三羧酸酯）]已被证明是一种活性多相催化剂，可用于亚甲基双萘酚的氧化环化和现代串联工艺（原位氧化-氨基形成-氧化顺序）。Fe（BTC）的这种潜在的催化效用使其对可持续工业化学具有相当大的吸引力。
• High-yielding TfOH-catalyzed condensation of phenols with aromatic aldehydes at high pressure. A model synthesis of the benzylidene biphenol key skeleton of blepharismins
  作者：Takeshi Ohishi、Tomoyuki Kojima、Tatsuomi Matsuoka、Motoo Shiro、Hiyoshizo Kotsuki

  DOI：10.1016/s0040-4039(01)00208-8

  日期：2001.3

  An approach to the benzylidene biphenol key component of blepharismins, photoreceptor pigments isolated from Blepharisma japonicum, is reported. This method relies on an efficient TfOH-catalyzed condensation of phenols with aromatic aldehydes in EtOH as a solvent at 3 kbar pressure.

  报导了一种方法，该方法可用于分离竹节菌属的苄叉基双酚关键成分，该竹节菌是从日本血吸虫中分离出来的光感受器色素。该方法依赖于在3 kbar压力下以EtOH为溶剂的苯酚与芳族醛在TfOH上的有效催化缩合。
• Synthesis and crystal structure of a dinuclear rhodium complex. Catalytic activity of mono- and di-nuclear rhodium phosphite complexes in hydroformylation
  作者：Esther K. van den Beuken、Wim G. J. de Lange、Piet W. N. M. Van Leeuwen、Nora Veldman、Anthony L. Spek、Ben L. Feringa

  DOI：10.1039/dt9960003561

  日期：——

  bidentate phosphite, bis[2-(diphenoxyphosphinoxy)-1-naphthyl]methyl}benzene L1 and a tetradentate phosphite, 1,4-bisbis[2-(diphenoxyphosphinoxy)-1-naphthyl]methyl}benzene L2 were prepared in a facile two-step procedure involving condensation of 2-naphthol with respectively benzaldehyde or terephthaladehyde, followed by treatment with chlorodiphenoxyphosphine. The corresponding monuclear rhodium(I) complex

  一种新的亚齿二亚磷酸酯，双[2-（二苯氧基次膦氧基）-1-萘基]甲基}苯L 1和四齿亚磷酸酯，1，4-双二[双[2-（二苯氧基次膦氧氧基）-1-萘基]甲基}苯L 2是涉及2-萘酚的缩合分别与苯甲醛或terephthaladehyde，随后用chlorodiphenoxyphosphine处理的简便两个步骤中制备。相应的单核铑（I）配合物[RhL 1（acac）] 1（acac =乙酰丙酮酸）和双核配合物[Rh 2 L 2（acac）2 ] 2和[Rh 2 L 2 Cl 2（CO）2] 3已被隔离。通过动态1 H和31 P NMR光谱研究了溶液中单核和双核铑配合物中配体的通量行为，表明联芳基甲烷单元的旋转受阻。通过X射线分析获得的配合物2的晶体结构显示出其双核性质和“未折叠”的几何形状。配合物1和2催化环己烯的加氢甲酰化，历时4小时，其平均周转频率分别为428和344 mm –1 h –
• 1,3-Dibromo-5,5-dimethylhydantoin (DBH)/kaolin: An efficient reagent system for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions
  作者：Farhad Shirini、Nader Ghaffari Khaligh、Gholam Hossein Imanzadeh、Parisa Ghods Ghasem-Abadi

  DOI：10.1016/j.cclet.2012.08.008

  日期：2012.10

  1,3-Dibromo-5,5-dimethylhydantoin, has been used as an efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes in the presence of kaolin. All reactions are performed in the absence of solvent in relatively short reaction times in good to high yields.

  1,3-二溴-5,5-二甲基乙内酰脲已被用作在高岭土存在下合成14-芳基-14 H-二苯并[ a，j ]黄嘌呤的有效催化剂。所有反应均在不存在溶剂的情况下以相对短的反应时间进行，以高至高收率进行。
• Synthesis of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth [1,2-e][1,3]oxazine derivatives via multicomponent approach
  作者：Ruli Borah、Arup Kumar Dutta、Parishmita Sarma、Champak Dutta、Bipul Sarma

  DOI：10.1039/c3ra47211f

  日期：——

  A series of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth [1,2-e][1,3]oxazine derivatives 6 were exclusively obtained in high yields for the first time through multicomponent reactions (MCRs) of 2-naphthol, aromatic aldehydes and electron rich primary amines in ethanol at room temperature using CCl3COOH as catalyst. The same reaction could be conducted effectively in solvent-free medium at 100 °C. The stereochemistry of the two hydrogens connected to C-2 and C-4 (1,3) positions of the oxazine ring are identified as anti-orientation by single crystal XRD, COSY and NOESY analysis.

  首次通过多组分反应（MCRs），在室温下使用三氯乙酸（CCl3COOH）作为催化剂，以2-萘酚、芳香醛和富电子的伯胺在乙醇中反应，高产率地合成了系列反式-2,3-二氢-1,2,3-三取代-1H-萘[1,2-e][1,3]噁嗪衍生物6。相同反应在无溶剂条件下于100°C也能有效进行。通过单晶XRD、COSY和NOESY分析，确定了噁嗪环的C-2和C-4（1,3）位置连接的两个氢的立体化学为反式构型。