1-(naphthalen-2-yl)-2-(tetrahydrofuran-2-yl)ethanone | 1166996-29-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(naphthalen-2-yl)-2-(tetrahydrofuran-2-yl)ethanone
• 英文别名: 1-Naphthalen-2-yl-2-(oxolan-2-yl)ethanone
• CAS: 1166996-29-7
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: MFYUMHJITLXPFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 氢氟酸 、 水 、 对甲苯磺酸 作用下， 以 环戊基甲醚 、 乙腈 为溶剂， 反应 24.0h， 生成 1-(naphthalen-2-yl)-2-(tetrahydrofuran-2-yl)ethanone
  参考文献：
  名称：

  Asymmetric Catalytic Cycloetherification Mediated by Bifunctional Organocatalysts

  摘要：

  Oxacyclic structures such as tetrahydrofuran (THF) rings are commonly found in many bioactive compounds, and this has led to several efforts toward their stereoselective syntheses. However, the process of catalytic asymmetric cycloetherification for their straightforward synthesis has remained a challenge. In this study, we demonstrate a novel asymmetric synthesis method for THF via the catalytic cycloetherification of epsilon-hydroxy-alpha,beta-unsaturated ketones mediated by cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This catalytic process represents a highly practical cycloetherification method that provides excellent enantioselectivities, even with low catalyst loadings at ambient temperature.

  DOI：

  10.1021/ja207322d

文献信息

• Copper-catalyzed dehydrogenative cross-coupling reaction between unactivated ethers and simple ketones mediated by pyrrolidine
  作者：Xing-Fen Huang、Zhi-Qiang Zhu、Zhi-Zhen Huang

  DOI：10.1016/j.tet.2013.07.085

  日期：2013.10

  A copper-catalyzed dehydrogenative cross-coupling reaction between unactivated ethers and simple ketones mediated by pyrrolidine has been developed. Under the catalysis of CuBr2 and in the presence of pyrrolidine, either tetrahydrofuran 2a or tetrahydropyran 2b can react smoothly with a series of methyl aryl ketones 1a–m to give desired coupling products 3aa–mb using TBHP as an oxidant. The advantages

  已开发了未活化的醚与吡咯烷介导的简单酮之间的铜催化的脱氢交叉偶联反应。在CuBr 2的催化下，在吡咯烷的存在下，四氢呋喃2a或四氢吡喃2b可以与一系列甲基芳基酮1a – m平稳反应，使用TBHP作为氧化剂得到所需的偶联产物3aa – mb。脱氢交叉偶联反应的优点是采用未改性的醚作为底物，对许多官能团具有良好的耐受性，并使用廉价的铜盐作为催化剂。提出了通过烯胺攻击的可能的自由基机制。
• Visible-light-promoted oxidative coupling of styrene with cyclic ethers
  作者：Golam Kibriya、Debashis Ghosh、Alakananda Hajra

  DOI：10.1007/s11426-019-9609-9

  日期：2020.1

  A new visible-light-promoted oxidative coupling of vinylarenes with cyclic ethers has been developed using rose bengal as photocatalyst and tert-butyl hydrogenperoxide (TBHP) as oxidant under ambient air at room temperature. A library of α-oxyalkylated ketones with broad functionalities has been synthesized in moderate to good yields. A radical mechanism is suggested for the present protocol

  在室温和室温下，使用玫瑰红作为光催化剂，叔丁基过氧化氢（TBHP）作为氧化剂，开发了一种新的可见光促进的乙烯基芳烃与环醚的氧化偶联反应。已经以中等至良好的产率合成了具有广泛功能的α-氧烷基化酮的文库。对于本协议，提出了一种根本性机制
• Organocatalytic Enantioselective Cycloetherifications Using a Cooperative Cation-Binding Catalyst
  作者：Amol P. Jadhav、Jeong-A Oh、In-Soo Hwang、Hailong Yan、Choong Eui Song

  DOI：10.1021/acs.orglett.8b02240

  日期：2018.9.7

  A highly enantioselective cycloetherification strategy for the straightforward synthesis of enantioenriched tetrahydrofurans, tetrahydropyrans, and oxepanes using Song’s cation-binding oligoEG catalyst and KF as the base is demonstrated. A wide range of ε-, ζ-, and η-hydroxy-α,β-unsaturated ketones were cyclized to the corresponding five-, six-, and seven-membered chiral oxacycles with high enantiopurity

  展示了一种高度对映体选择性的环醚化策略，该策略可使用Song的阳离子结合寡聚EG催化剂和KF作为碱直接合成富对映体的四氢呋喃，四氢吡喃和氧杂环丁烷。各种各样的ε-，ζ-和η-羟基-α，β-不饱和酮被环化成具有高对映体纯度的相应的五元，六元和七元手性氧杂环。这种非常成功的催化作用可归因于由手性催化剂，底物和KF原位生成的密闭超分子手性笼中的系统协同阳离子结合催化。
• Visible-light induced eosin Y catalysed C(sp2)-H alkylation of carbonyl substrates via direct HAT
  作者：Satya Prakash Singh、Vishal Srivastava、Pravin K. Singh、Praveen P. Singh

  DOI：10.1016/j.tet.2023.133245

  日期：2023.2

  (HAT) catalyst for C–H activation. A study that utilized the alkylation of C–H bonds with electron-deficient alkenes as a paradigm provided a very wide substrate scope that made it simple to access a number of significant synthons. This green and sustainable eosin Y-based photocatalytic hydrogen atom transfer method promises to diversify the functionalization of a variety of native C–H bonds.

  已经提出了可见光驱动的有机转化，使用曙红 Y，一种广泛使用且价格合理的金属催化剂替代品，它也可以作为 C-H 活化的有效直接氢原子转移 (HAT) 催化剂。一项利用 C-H 键与缺电子烯烃的烷基化作为范例的研究提供了非常广泛的底物范围，使得获得许多重要的合成子变得容易。这种绿色且可持续的基于曙红 Y 的光催化氢原子转移方法有望使各种天然 C-H 键的功能化多样化。
• Visible-Light-Driven Denitrogenative C–C Bond Formation and Oxidative Difunctionalization of Vinyl Azides
  作者：Adinath Majee、Santosh Sing Sardar、Aramita De、Satyajit Pal、Subhankar Sarkar、Sougata Santra、Grigory V. Zyryanov

  DOI：10.1055/a-2131-3208

  日期：2024.2

  A newer synthetic protocol has been developed to synthesize α-oxyalkyl ketones from vinyl azides under transition-metal-free reaction conditions. The reaction proceeds in the presence of organic photoredox catalyst rose bengal, an oxidant tert-butyl hydroperoxide (TBHP), and ethers. A broad range of substituted vinyl azides were found to react smoothly upon visible-light irradiation, which readily

  开发了一种新的合成方案，可以在无过渡金属的反应条件下从乙烯基叠氮化物合成 α-氧基烷基酮。该反应在有机光氧化还原催化剂玫瑰红（一种氧化剂叔胺）的存在下进行-丁基氢过氧化物（TBHP）和醚。人们发现多种取代的乙烯基叠氮化物在可见光照射下可以顺利反应，这很容易提供相关产品。已经进行了一些对照实验来提出可能的机制。该过程由乙烯基叠氮化物的自由基加成引发，这触发了由二氮损失驱动的级联断裂机制，稳定的醚自由基最终产生α-氧基烷基酮。该方法提供了一种简单、温和、直接、新颖的制备α-烷氧基酮的范例。