4-(1,2,3,4-tetrahydronaphthalen-1-yl)benzonitrile | 132777-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4-(1,2,3,4-tetrahydronaphthalen-1-yl)benzonitrile
• CAS: 132777-28-7
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: FVDVTATYJTVIAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(p-Cyanophenyl)-4-phenylbutan-1-ol 在 四氯化钛 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以90%的产率得到4-(1,2,3,4-tetrahydronaphthalen-1-yl)benzonitrile
  参考文献：
  名称：

  A systematic study of benzyl cation initiated cyclization reactions

  摘要：

  A systematic investigation of benzyl cation initiated cyclization reactions to form six-membered carbocycles is presented. The generation of benzyl cations from benzylic bromides, ethers, and alcohols followed by intramolecular capture provided good yields of cyclized products by use of several different cyclization terminators (e.g., phenyl, alkene, beta-keto ester). A study on the effect of changing the electronic nature of substituents para to the benzyl cation showed that even electron-withdrawing substituents such as quaternary ammonium afford high yields of cyclization products. The formation of five- and seven-membered carbocycles was briefly investigated and found to be less general than the formation of the corresponding six-membered carbocycles.

  DOI：

  10.1021/jo00008a049

文献信息

• Visible-light-mediated external-reductant-free reductive cross coupling of benzylammonium salts with (hetero)aryl nitriles
  作者：Meng Miao、Li-Li Liao、Guang-Mei Cao、Wen-Jun Zhou、Da-Gang Yu

  DOI：10.1007/s11426-019-9597-8

  日期：2019.11

  Herein we report a novel visible-light-mediated external reductant-free reductive cross coupling for the construction of C sp2–C sp3 bonds. A variety of benzylammonium salts underwent selective coupling with (hetero)aryl nitriles to deliver important diarylmethanes under mild reaction conditions. Importantly, photocatalysts can be omitted for many cases, which might involve the electron donor acceptor

  在这里，我们报告了一种新型的可见光介导的无外部还原剂的还原性交叉偶联，用于构建C sp 2 –C sp 3键。各种苄基铵盐与（杂）芳基腈进行选择性偶联，以在温和的反应条件下提供重要的二芳基甲烷。重要的是，在许多情况下可以省略光催化剂，这可能涉及电子给体受体（EDA）配合物。机理研究表明，苄基可能是关键的中间体。此外，通过裂解铵盐中的C–N键原位生成的NMe 3充当电子给体，因此避免了使用外部还原剂。
• Switchable Direct Oxygenative Arylation of C(sp³)–H Bonds via Electrophotocatalysis
  作者：Yan Zhang、Xiang Sun、Ji-Hu Su、Tong Li、Chengbin Du、Kuiliang Li、Qi Sun、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.orglett.3c01751

  日期：2023.7.14

  A metal-free electrophotochemical C(sp3)-H arylation was developed under mild conditions. This method enables a switchable synthesis of diaryl alcohols and diaryl alkanes from inactive benzylic carbons. More importantly, a cheap and safe mediator N-chlorosuccinimide (NCS) was developed, which was employed for the hydrogen atom transfer (HAT) process of the benzylic C–H bond. In addition, this active

  在温和条件下开发了无金属的电化学C(sp 3 )-H芳基化反应。该方法能够从不活泼的苄基碳可转换地合成二芳基醇和二芳基烷烃。更重要的是，开发了一种廉价且安全的介体N-氯代琥珀酰亚胺（NCS），用于苄基C-H键的氢原子转移（HAT）过程。此外，该活性自由基被电子顺磁共振（EPR）捕获并识别。
• Direct C(sp³)–H Arylation of Unprotected Benzyl Anilines and Alkylarenes by Organocatalysis under Visible Light
  作者：Cheng Huang、Peng Xiao、Zhong-Ming Ye、Chen-Lu Wang、Chen Kang、Sheng Tang、Zhenhong Wei、Hu Cai

  DOI：10.1021/acs.orglett.3c03980

  日期：2024.1.12

  alkylarenes via consecutive photoinduced electron transfer by visible light irradiation. Reductive quenching cycles and radical–radical cross-coupling were involved, and electron paramagnetic resonance experiments provide evidence for the formation of radical intermediates formed in situ. The protocol highlights transition metal free, external oxidant free, broad substrate scope, and high efficiency (>60 examples

  本文报道了未受保护的苄基苯胺和烷基芳烃通过可见光照射连续光诱导电子转移的直接C(sp 3 )–H芳基化。涉及还原猝灭循环和自由基-自由基交叉偶联，电子顺磁共振实验为原位形成自由基中间体的形成提供了证据。该协议强调不含过渡金属、不含外部氧化剂、底物范围广泛和效率高（> 60 个示例，高达 96%）。
• Benzylic C–H arylation with dicyanoarenes<i>via</i>convergent paired electrolysis
  作者：Shanyu Tang、Guillaume Vincent

  DOI：10.1039/d3gc00866e

  日期：——

  methylarene derivatives and 1,4-dicyanoarenes to perform the arylative functionalization of a benzylic C(sp3)–H bond to form 1,1-biarylmethane derivatives that are found in several drugs and biologically active compounds. This electrochemical process proceeds via the coupling of a benzylic radical or a benzylic carbocation with a 1,4-dicyanoarene radical anion to form the desired C–C bond followed by

  我们描述了甲基芳烃衍生物和 1,4-二氰基芳烃的汇聚配对电解，以对苄基 C(sp 3 )–H 键进行芳基化官能化，形成 1,1-联芳基甲烷衍生物，这些衍生物存在于多种药物和生物活性化合物中。该电化学过程通过苯甲基自由基或苯甲基碳正离子与 1,4-二氰基芳烃自由基阴离子偶联，形成所需的 C-C 键，然后消除氰化物阴离子，氰化物阴离子可能被醛捕获为氰醇。这些活性物质分别通过阳极处的苄基底物的氧化和阴极处的二氰基芳烃的还原而产生。我们克服的关键挑战之一是避免在获得的联芳基甲烷产物的双苄基位置形成过氧化的偶联产物。
• Electrochemical deoxygenative arylation of aldehydes and ketones
  作者：Meng Li、Yue Tian、Kunhui Sun、Zhimin Xu、Lifang Tian、Yahui Wang

  DOI：10.1039/d3cc01395b

  日期：——

  of trivalent phosphine under electrochemical conditions. Reductive coupling between electron-deficient arenes and the carbonyl groups of aldehydes or ketones occurs at the cathode to yield diaryl alcohols. At the anode, the trivalent phosphine reagent may undergo single-electron oxidation to generate its radical cation, which reacts with the diaryl alcohols to form dehydroxylated products.

  在电化学条件下，在三价膦的存在下，从芳香醛或酮与缺电子芳烃构建二芳基烷烃。缺电子芳烃与醛或酮的羰基之间的还原偶联发生在阴极，生成二芳基醇。在阳极，三价膦试剂可以进行单电子氧化以产生其自由基阳离子，其与二芳基醇反应形成脱羟基产物。