1-benzhydryl-2-hydroxynaphthalene | 52449-12-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-benzhydryl-2-hydroxynaphthalene
• 英文别名: 1-(Diphenylmethyl)-2-naphthol；1-benzhydrylnaphthalen-2-ol；1-Benzhydryl-[2]naphthol；2-Hydroxy-1-naphthyl-diphenylmethan；1-Benzhydryl-naphthol-(2)
• CAS: 52449-12-4
• 化学式: C₂₃H₁₈O
• 分子量: 310.395
• InChiKey: QFXSOXGCWMIEBB-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  482.3±14.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  1-benzhydryl-2-hydroxynaphthalene 、 2-二乙氨基氯乙烷盐酸盐 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以67%的产率得到2-[(1-benzhydryl-2-naphthyl)oxy]-N,N-diethyl-ethanamine
  参考文献：
  名称：

  Design, synthesis and antitubercular activity of diarylmethylnaphthol derivatives

  摘要：

  A new series of diarylmethylnapthyloxy ethylamines were synthesized by antinoalkylation of diarylmethylnaphthols which were obtained by Friedel-Crafts alkylation on 1- and 2-naphthols using diarylcarbinols as the alkylating agents. The title compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Rv, in vitro and showed MIC in the range of 3.12-25 mu g/ml. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.089
• 作为产物：
  描述：

  benzhydryl[2,2,2-trifluoro-1-(1H-indol-3-yl)ethyl]amine 在 盐酸 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 1-benzhydryl-2-hydroxynaphthalene
  参考文献：
  名称：

  BF3 促进 N-烷基α-三氟甲基化亚胺的芳香取代：1-Aryl-2,2,2-trifluoroethylamines 的简便合成

  摘要：

  从伯烷基胺和三氟乙醛乙基半缩醛中获得的三种代表性 N-烷基三氟甲基亚胺 1a-c（R：a，苄基；b，二苯甲基；c，甲基）的芳族取代用于研究 1-芳基的制备-2,2,2-三氟乙胺。在BF3·OEt2的存在下，亚胺1与各种芳香族化合物在室温下反应顺利进行，得到了中高产率的N-烷基-1-芳基-2,2,2-三氟乙胺。此外，通过在盐酸中水解或通过钯催化的氢解，成功地区域选择性去除 N-苄基和 N-二苯甲基。

  DOI：

  10.1246/bcsj.75.2637

文献信息

• Protecting group-free use of alcohols as carbon electrophiles in atom efficient aluminium triflate-catalysed dehydrative nucleophilic displacement reactions
  作者：Adam Cullen、Alfred J. Muller、D. Bradley G. Williams

  DOI：10.1039/c7ra08784e

  日期：——

  Benzylic and allylic alcohols are rendered electrophilic without chemical modification by the use of aluminium triflate as catalyst. The reaction succeeds with alcohol, thiol, carbon and nitrogen nucleophiles. When phenols are employed as nucleophiles, C-alkylation ensues. An advanced application of the method is demonstrated in the synthesis of 2H-chromenes and their N and S analogues.

  通过使用三氟甲磺酸铝作为催化剂，无需化学改性即可将苯甲酸和烯丙醇亲电子化。该反应通过醇，硫醇，碳和氮亲核试剂成功进行。当苯酚用作亲核试剂时，随后发生C-烷基化。该方法的先进应用在2 H-色烯及其N和S类似物的合成中得到了证明。
• An Efficient and General Iron-Catalyzed CC Bond Activation with 1,3-Dicarbonyl Units as a Leaving Groups
  作者：Huanrong Li、Wenjuan Li、Weiping Liu、Zhiheng He、Zhiping Li

  DOI：10.1002/anie.201006779

  日期：2011.3.21

  With our compliments: The 1,3‐dicarbonyl unit has been shown to be a new and useful leaving group for iron‐catalyzed bond cleavage (see scheme). This new strategy can complement the traditional Friedel–Crafts reaction and was applied in the synthesis of indene derivatives.

  在我们的赞美中：1,3-二羰基单元已被证明是一个新的有用的离去基团，可用于铁催化的键裂解（请参见方案）。这种新的策略可以补充传统的Friedel-Crafts反应，并被用于合成茚衍生物。
• Phosphomolybdic acid as a bifunctional catalyst for Friedel-Crafts type dehydrative coupling reaction
  作者：Guo-Ping Yang、Dilireba Dilixiati、Tao Yang、Dong Liu、Bing Yu、Chang-Wen Hu

  DOI：10.1002/aoc.4450

  日期：2018.9

  Phosphomolybdic acid (H3PMo12O40) was found to be a bifunctional catalyst for C─C bond formation via the dehydrative reaction of diarylmethanols with various nucleophiles, including 2‐naphthols, indoles, benzofuran and benzothiophene. The protons in the catalyst might play a critical role in the activation of alcohol, while the polyanion was advantageous for stabilizing the carbocation species. The

  磷钼酸（H 3 PMo 12 O 40）是通过二芳基甲醇与各种亲核试剂，包括2-萘酚，吲哚，苯并呋喃和苯并噻吩的脱水反应，形成C-C键的双功能催化剂。催化剂中的质子可能在醇的活化中起关键作用，而聚阴离子有利于稳定碳正离子。协同催化体系显示出其自身的优点，例如高反应速率，低催化剂负载，温和的条件，极好的收率（高达99％）和良好的官能团相容性。
• Direct alkylation of aromatics using alcohols in the presence of NaHSO4/SiO2
  作者：Yuta Sato、Tadashi Aoyama、Toshio Takido、Mitsuo Kodomari

  DOI：10.1016/j.tet.2012.06.063

  日期：2012.9

  Simple and efficient procedure for alkylation of aromatics from alcohols in the presence of NaHSO4/SiO2 was developed. Various triaryl methanes were obtained in good yields in short reaction time. For instance the reaction of mesitylene with benzhydrol in the presence of NaHSO4/SiO2 gave the corresponding triaryl methane in a quantitative yield. NaHSO4/SiO2 was regenerated by simple treatment and could

  在NaHSO 4 / SiO 2的存在下，开发了一种简单有效的从醇类将芳烃烷基化的方法。在短的反应时间内以高收率获得了各种三芳基甲烷。例如，在NaHSO 4 / SiO 2的存在下，1，3，5-三甲基苯与苯甲醇的反应以定量收率得到了相应的三芳基甲烷。NaHSO 4 / SiO 2通过简单处理即可再生，可以循环使用八次而不会损失活性。
• Microwave assisted benzylation of naphthols and 4-hydroxycoumarin under catalyst & solvent free conditions
  作者：Ravikrishna Dada、Garima Singh、Abhishek Pareek、Saeen Kausar、Srinivasarao Yaragorla

  DOI：10.1016/j.tetlet.2016.07.010

  日期：2016.8

  An expeditious and highly practical, microwave assisted benzylation of naphthols and 4-hydroxycoumarin has been developed under catalyst-free & solvent-free conditions. Alcohols undergo heat induced dehydration to form ethers, which collapse reversibly to form the carbocation which was captured immediately by a suitable nucleophile to furnish the benzylated compounds.

  在无催化剂和无溶剂的条件下，开发了一种快速且高度实用的萘酚和4-羟基香豆素的微波辅助苄基化方法。醇经历热诱导的脱水以形成醚，醚可逆地塌陷以形成碳阳离子，该碳阳离子被合适的亲核试剂立即捕获以提供苄基化的化合物。