naphthalen-2-yl 2-bromo-2-methylpropanoate | 96887-94-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-2-yl 2-bromo-2-methylpropanoate
• 英文别名: α-bromo-isobutyric acid-[2]naphthyl ester；β-Naphthyl-(α-brom-isobutyrat)；α-Brom-isobuttersaeure-[2]naphthylester；α-Brom-isobuttersaeure-β-naphthylester；Naphthalen-2-yl 2-bromo-2-methylpropanoate
• CAS: 96887-94-4
• 化学式: C₁₄H₁₃BrO₂
• 分子量: 293.16
• InChiKey: IHRJPEYNTYBVBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  naphthalen-2-yl 2-bromo-2-methylpropanoate 、 sodium 2-naphtholate 在 xylene 作用下， 生成 α-[2]naphthyloxy-isobutyric acid-[2]naphthyl ester
  参考文献：
  名称：

  Bischoff, Chemische Berichte, 1906, vol. 39, p. 3847

  摘要：

  DOI：
• 作为产物：
  描述：

  2-溴-2-甲基丙酰溴 、 1-萘酚钠 在 苯 作用下， 生成 naphthalen-2-yl 2-bromo-2-methylpropanoate
  参考文献：
  名称：

  Bischoff, Chemische Berichte, 1906, vol. 39, p. 3847

  摘要：

  DOI：

文献信息

• Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation
  作者：Xinyi Ren、Chaoren Shen、Guangzhu Wang、Zhanglin Shi、Xinxin Tian、Kaiwu Dong

  DOI：10.1021/acs.orglett.1c00465

  日期：2021.4.2

  was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.

  开发了使用亲电子氰化试剂和锌还原剂对叔烷基溴进行还原性氰化的反应，在温和的反应条件下，提供了多种含氰基全碳四元中心的α-氰基酮，酯和羧酰胺，收率良好。通过密度泛函理论计算，阐明了相应的反应机理，包括原位生成的有机锌试剂和反应性的区别。
• Responsive Interfacial Assemblies Based on Charge‐Transfer Interactions
  作者：Shuyi Sun、Chenxia Xie、Jie Chen、Yang Yang、Hui Li、Thomas P. Russell、Shaowei Shi

  DOI：10.1002/anie.202111252

  日期：2021.12.6

  By taking advantage of charge transfer (CT) interactions between water-soluble electron-deficient acceptor and oil-soluble electron-rich donor, the formation and assembly of CT complex surfactants (CTCSs) at the oil–water interface is presented. With CTCSs as the building block, higher-order nanofilms with exceptional mechanical properties are produced, which can be used to stabilize and structure

  利用水溶性缺电子受体和油溶性富电子供体之间的电荷转移（CT）相互作用，提出了油水界面CT复合表面活性剂（CTCS）的形成和组装。以 CTCS 为基础，生产出具有优异机械性能的高阶纳米薄膜，可用于稳定和构建液体。
• Synthesizing Complex Quaternary Carbons by the Sequence-Regulated Additions of <i>tert</i>-Alkyl Radicals to Two Different Olefins
  作者：Kyosuke Matsuda、Chihiro Tanaka、Daisuke Sato、Takashi Nishikata

  DOI：10.1021/acs.orglett.3c00812

  日期：2023.4.28

  We report the sequence-regulated radical additions of tert-alkyl radicals to two different olefins controlled by a Cu catalyst, which we term the “atom-transfer radical addition–substitution” reaction. The reactions of α-bromocarbonyl compounds, such as tert-alkyl radical sources, with methacrylates and styrenes occur in a sequence-regulated manner to give the corresponding three-component product

  我们报告了由 Cu 催化剂控制的叔烷基自由基对两种不同烯烃的序列调节自由基加成，我们将其称为“原子转移自由基加成-取代”反应。α-溴代羰基化合物（例如叔烷基自由基源）与甲基丙烯酸酯和苯乙烯的反应以顺序调节的方式发生，得到相应的具有跳过季碳中心的三组分产物。我们的方法为如何在受调节的脂肪链合成过程中控制叔烷基自由基的反应性提供了新的见解。
• Copper-Catalyzed Bifunctionalization/Annulation of Unactivated Alkene with Alkyl Bromides
  作者：Cancan Feng、Yangjie Wu

  DOI：10.1021/acs.joc.3c01746

  日期：2023.11.3

  from unactivated alkenes and alkyl bromides via a Cu-catalyzed inter-/intramolecular carboamidation. This reaction proceeded smoothly under mild reaction conditions and exhibited a broad substrate scope and various functional groups. This protocol is not only compatible with 1, 2, and 3° alkyl bromides but also suitable for α-bromo nitrile as well as various benzyl bromides. The mechanism exploration

  β-内酰胺是生物活性化合物和药物中普遍存在的支架。在此，我们公开了一种从未活化的烯烃和烷基溴出发，通过 Cu 催化的分子间/分子内碳酰胺化反应构建 β-内酰胺的简化方法。该反应在温和的反应条件下顺利进行，并表现出广泛的底物范围和丰富的官能团。该方案不仅与 1、2 和 3° 烷基溴兼容，而且还适用于 α-溴腈以及各种苄基溴。机理探索表明涉及顺序自由基加成/还原消除。
• Triply Triggered Doxorubicin Release From Supramolecular Nanocontainers
  作者：Xian Jun Loh、Jesús del Barrio、Pearl Pei Chern Toh、Tung-Chun Lee、Dezhi Jiao、Urs Rauwald、Eric A. Appel、Oren A. Scherman

  DOI：10.1021/bm201588m

  日期：2012.1.9

  The synthesis of a supramolecular double hydrophilic block copolymer (DHBC) held together by cucurbit[8]uril (CB[8]) ternary complexation and its subsequent self-assembly into micelles is described. This system is responsive to multiple external triggers including temperature, pH and the addition of a competitive guest. The supramolecular block copolymer assembly consists of poly(N-isopropylacrylamide) (PNIPAAm) as a thermoresponsive block and poly(dimethylaminoethylmethacrylate) (PDMAE-MA) as a pH-responsive block. Moreover, encapsulation and controlled drug release was demonstrated with this system using the chemotherapeutic drug doxorubicin (DOX). This triple stimuli responsive DHBC micelle system represents an evolution over conventional double stimuli responsive covalent diblock copolymer systems and displayed a significant reduction in the viability of HeLa cells upon triggered release of DOX from the supramolecular micellar nanocontainers.