1-(1-phenylbut-3-enyl)-2-naphthol | 1262848-28-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-phenylbut-3-enyl)-2-naphthol
• 英文别名: 1-(1-Phenylbut-3-enyl)naphthalen-2-ol；1-(1-phenylbut-3-enyl)naphthalen-2-ol
• CAS: 1262848-28-1
• 化学式: C₂₀H₁₈O
• 分子量: 274.362
• InChiKey: WOQLUFYRGPASBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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-[(phenyl)(p-tosyl)methyl]-2-naphthol 、 烯丙基三丁基锡 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以89%的产率得到1-(1-phenylbut-3-enyl)-2-naphthol
  参考文献：
  名称：

  Friedel-Crafts Reactions of 2-Naphthol with α-Amido Sulfones and Conversion of the Products with Nucleophiles¹

  摘要：

  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。

  DOI：

  10.1055/s-0030-1258218

文献信息

• Allylsilane Reagent‐Controlled Divergent Asymmetric Catalytic Reactions of 2‐Naphthoquinone‐1‐methide
  作者：Xiangfeng Lin、Yan Liu、Can Li

  DOI：10.1002/chem.202002814

  日期：2020.11.6

  and highly stereoselective (up to 96.5:3.5 e.r.) manner under mild conditions. Moreover, it is demonstrated that 2‐Nap‐Q‐1‐M can serve as an efficient diene for a side asymmetric Diels–Alder (D‐A) reaction. This principle can provide a straightforward access to hydrophenalene in an optically active form, which represents a structural core of various natural products and bioactive molecules.

  在此，在Sc III /报道了Feng配体复合物。通过这些方法，可以在温和的条件下以直接且高度立体选择性（高达96.5：3.5 er）的方式获得各种独特取代的手性烯丙基官能化的二芳基化合物和萘并吡喃产物。此外，已证明2-Nap-Q-1-M可以用作侧面不对称Diels-Alder（D-A）反应的有效二烯。该原理可以提供光学活性形式的对苯二酚的直接途径，其代表各种天然产物和生物活性分子的结构核心。
• 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.