4-iodo-N-((3,4-dihydronaphthalen-1-yl)methyl)benzamide | 1359180-14-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 4-iodo-N-((3,4-dihydronaphthalen-1-yl)methyl)benzamide
• 英文别名: N-(3,4-dihydronaphthalen-1-ylmethyl)-4-iodobenzamide
• CAS: 1359180-14-5
• 化学式: C₁₈H₁₆INO
• 分子量: 389.236
• InChiKey: VHNHBJNMDBUBBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-iodo-N-((3,4-dihydronaphthalen-1-yl)methyl)benzamide 在 sodium carbonate 、 Selectfluor 作用下， 以 hexanes 、 氟苯 为溶剂， 反应 24.0h， 以71%的产率得到(1R,2S)-2'-(4-iodophenyl)-2-fluoro-3,4-dihydro-2H,4'H-spiro[naphthalene-1,5'-oxazole]
  参考文献：
  名称：

  Asymmetric Electrophilic Fluorination Using an Anionic Chiral Phase-Transfer Catalyst

  摘要：

  一个手性磷酸根离子发挥双重作用，促使氟化试剂溶解，然后在其中催化其反应。

  DOI：

  10.1126/science.1213918
• 作为产物：
  描述：

  3,4-二氢-1(2H)-萘酮 在 4-二甲氨基吡啶 、 aluminum (III) chloride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 4-iodo-N-((3,4-dihydronaphthalen-1-yl)methyl)benzamide
  参考文献：
  名称：

  Anti-Diastereoselective Synthesis of CF₃-Containing Spirooxazolines and Spirooxazines via Regiospecific Trifluoromethylative Spirocyclization by Photoredox Catalysis

  摘要：

  A novel synthesis of CF3-containing spirooxazolines and spirooxazines has been developed. Regiospecific trifluoromethylative spirocyclization (CF3-spirocyclization) of cyclic alkenes bearing an amide pendant mediated by photoredox catalysis is a useful strategy for construction of a C(sp(3))-CF3 bond and an spirooxazoline or spirooxazine ring onto C = C bonds via a single step. The key intermediate is alpha-CF3-substituted carbocationic species smoothly generated from single-electron-transfer (SET) photoredox processes, which results in diastereoselective spirocyclization. This is the first example of synthesis of CF3-containing spirooxazolines and spirooxazines in anti-fashion with respect to the CF3 group and the oxygen atom of the spirocycles.

  DOI：

  10.1021/acs.orglett.5b01694

文献信息

• [EN] ASYMMETRIC ELECTROPHILIC FLUORINATION USING AN ANIONIC CHIRAL PHASE-TRANSFER CATALYST<br/>[FR] FLUORATION ÉLECTROPHILE ASYMÉTRIQUE UTILISANT UN CATALYSEUR DE TRANSFERT DE PHASE CHIRAL ANIONIQUE
  申请人：UNIV CALIFORNIA

  公开号：WO2013096971A1

  公开（公告）日：2013-06-27

  The discovery of distinct modes of asymmetric catalysis has the potential to rapidly advance chemists' ability to build enantioenriched molecules. As an example, the use of chiral cation salts as phase-transfer catalysts for anionic reagents has enabled a vast set of enantioselective transformations. A largely overlooked analogous mechanism wherein a chiral anionic catalyst brings a cationic species into solution is itself a powerful method. The concept is broadly applicable to a number of different reaction pathways, including to the enantioselective fluorocyclization of olefins, and dearomatization of aromatic systems with a cationic electrophile-transferring (e.g., fluorinating) agent and a chiral phosphate catalyst. The reactions proceed in high yield and stereoselectivity. The compounds and methods of the invention are of particular value, especially considering the scarcity of alternative approaches.

  发现不对称催化的不同模式具有潜力快速推动化学家构建手性富集分子的能力。例如，使用手性阳离子盐作为相转移催化剂用于阴离子试剂已经实现了大量手性选择性转化。一个被大多数人忽视的类似机制是手性阴离子催化剂将阳离子物种溶解到溶液中，这本身就是一种强大的方法。这一概念广泛适用于许多不同的反应途径，包括对烯烃进行手性选择性氟环化和用阳离子亲电试剂转移（例如，氟化）剂和手性磷酸盐催化剂进行芳香系统去芳构化。这些反应产率高，立体选择性好。该发明的化合物和方法具有特殊价值，尤其考虑到替代方法的稀缺性。
• ASYMMETRIC ELECTROPHILIC FLUORINATION USING AN ANIONIC CHIRAL PHASE-TRANSFER CATALYST
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20140350253A1

  公开（公告）日：2014-11-27

  The discovery of distinct modes of asymmetric catalysis has the potential to rapidly advance chemists' ability to build enantioenriched molecules. As an example, the use of chiral cation salts as phase-transfer catalysts for anionic reagents has enabled a vast set of enantioselective transformations. A largely overlooked analogous mechanism wherein a chiral anionic catalyst brings a cationic species into solution is itself a powerful method. The concept is broadly applicable to a number of different reaction pathways, including to the enantioselective fluorocyclization of olefins, and dearomatization of aromatic systems with a cationic electrophile-transferring (e.g., fluorinating) agent and a chiral phosphate catalyst. The reactions proceed in high yield and stereoselectivity. The compounds and methods of the invention are of particular value, especially considering the scarcity of alternative approaches.

  不对称催化的不同模式的发现有潜力快速推进化学家构建对映富集分子的能力。例如，手性阳离子盐作为相转移催化剂用于阴离子试剂的使用已经实现了广泛的对映选择性转化。一个被大多数人忽视的类似机理是手性阴离子催化剂将阳离子物种溶解进溶液中的强大方法。这个概念广泛适用于许多不同的反应途径，包括烯烃的对映选择性氟杂环化和芳香体系的脱芳香化，使用离子型电子亲合试剂（例如氟化试剂）和手性磷酸盐催化剂。反应具有高产率和立体选择性。该发明的化合物和方法具有特殊价值，特别是考虑到替代方法的稀缺性。
• US9981977B2
  申请人：——

  公开号：US9981977B2

  公开（公告）日：2018-05-29