1-((4-methoxyphenyl)(phenyl)methyl)naphthalen-2-ol | 1262848-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((4-methoxyphenyl)(phenyl)methyl)naphthalen-2-ol
• 英文别名: 1-[(4-methoxyphenyl)(phenyl)methyl]-2-naphtho；1-[(4-methoxyphenyl)(phenyl)methyl]-2-naphthol；1-[(4-Methoxyphenyl)-phenylmethyl]naphthalen-2-ol；1-[(4-methoxyphenyl)-phenylmethyl]naphthalen-2-ol
• CAS: 1262848-29-2
• 化学式: C₂₄H₂₀O₂
• 分子量: 340.422
• InChiKey: NRPYGMADXJBPKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲氧基二苯甲醇 、 2-萘酚 在 phosphomolybdic acid 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以97%的产率得到1-((4-methoxyphenyl)(phenyl)methyl)naphthalen-2-ol
  参考文献：
  名称：

  磷钼酸作为Friedel-Crafts型脱水偶联反应的双功能催化剂

  摘要：

  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。

  DOI：

  10.1002/aoc.4450

文献信息

• Transition-Metal-Free Arylation and Alkylation of Diarylmethyl <i>p</i>-Tolyl Sulfones with Zinc Reagents
  作者：Maozhong Miao、Wenguang Yin、Lei Wang、Zhengkai Chen、Jianfeng Xu、Hongjun Ren

  DOI：10.1021/acs.joc.8b01428

  日期：2018.9.7

  The transition-metal-free synthesis of unsymmetrical and highly functionalized triarylmethanes through arylation of the situ generated o-QMs from diarylmethyl p-tolyl sulfones with aryl zinc reagents is described. Alkyl zinc reagents are also well tolerated in this reaction. Additionally, the straightforward synthesis of the analogue of the antituberculosis agent A and the key precursor of the anti-breast-cancer

  描述了不对称金属和高度官能化的三芳基甲烷的无过渡金属合成，该芳基通过芳基锌试剂芳基化二芳基甲基对甲苯砜中的原位生成的o- QM来合成。烷基锌试剂在该反应中也具有良好的耐受性。另外，通过该策略实现了抗结核剂A的类似物和抗乳腺癌剂B的关键前体的直接合成。
• Friedel-Crafts Reactions of 2-Naphthol with α-Amido Sulfones and Conversion of the Products with Nucleophiles¹
  作者：Biswanath Das、Cheruku Reddy、Chava Sindhu、Chithaluri Sudhakar、Siddavatam Nagendra

  DOI：10.1055/s-0030-1258218

  日期：2010.11

  2-Naphthol underwent Friedel-Crafts reaction with N-benzyloxycarbonylamino sulfones in the presence of InCl3 at room temperature to form the corresponding sulfonyl derivatives in high yields. The products were subsequently reacted with nucleophiles such as allyltributyltin and anisole to replace the sulfonyl group.

  在 InCl3 存在下，2-萘酚与 N-苄氧羰基氨基砜在室温下发生 Friedel-Crafts 反应，生成相应的磺酰衍生物，产量很高。这些产物随后与烯丙基三丁基锡和苯甲醚等亲核物反应，以取代磺酰基。
• Multicomponent one-pot synthesis of 2-naphthol derivatives and evaluation of their anticancer activity
  作者：Biswanath Das、Cheruku Ravindra Reddy、Jajula Kashanna、Suman Kumar Mamidyala、Chityal Ganesh Kumar

  DOI：10.1007/s00044-011-9884-x

  日期：2012.10

  Treatment of 2-naphthol with aldehydes and allyl tributyl stannane or anisole in the presence of AlCl3 at 0A degrees C to room temperature afforded its 1-alkyl derivatives in high yields (76-83%) within 4-8 h. The products were evaluated for their cytotoxic activity against four human cancer cell lines. The most potent compound (5d) showed IC50 of 1.2 +/- A 1.1, 1.6 +/- A 1.0, 0.9 +/- A 0.1, and 0.8 +/- A 0.4 mu M against Hep G(2), A549, MDA 231, and HeLa cell lines, respectively, and its activity was found to be comparable to that of doxorubicin.A new multicomponent synthesis of 2-naphthol derivatives has been developed. The cytotoxic activity of one of the 2-naphthol derivatives (A:R = 4-F-C6H5) was comparable to that of doxorubicin.