2-(4-bromophenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline | 1189050-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-(4-bromophenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-(4-bromophenyl)-1-(nitromethyl)-3,4-dihydro-1H-isoquinoline
• CAS: 1189050-55-2
• 化学式: C₁₆H₁₅BrN₂O₂
• 分子量: 347.211
• InChiKey: KZIYTKOBTRZXEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline 在 盐酸 、 亚硝酸特丁酯 、 水 、 氧气 作用下， 以 1,4-二氧六环 为溶剂， 以61 %的产率得到3,4-bis(2-(2-((4-bromophenyl)(nitroso)amino)ethyl)benzoyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  Tert‐Butyl Nitrite‐initiated C−N Bond Cleavage of 1‐Nitromethyl‐N‐aryltetrahydroisoquinolines: Synthesis of Furoxans with N−NO Skeleton

  摘要：

  AbstractA series of furoxan derivatives with N‐nitroso groups were synthesized in good yields by TBN initiated radical sp3 C−N bond cleavage of 1‐nitromethyl‐N‐aryltetrahydroisoquinolines. This reaction grafts the biologically important furoxan skeleton and N‐nitroso group into on molecule, greatly improving the molecular complexity in one step transformation. The mechanistic study shows that this reaction is mediated by the in situ generated α‐carbonyl nitrile oxide, which is afforded by TBN promoted C−N bond cleavage.

  DOI：

  10.1002/asia.202201265
• 作为产物：
  描述：

  2-苯基-1,2,3,4-四氢异喹啉 在 N-溴代丁二酰亚胺(NBS) 、 ammonium acetate 、 氧气 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 18.17h， 生成 2-(4-bromophenyl)-1-(nitromethyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Acetic Acid Promoted Metal-Free Aerobic Carbon–Carbon Bond Forming Reactions at α-Position of Tertiary Amines

  摘要：

  The oxidative functionalization of the benzylic C-H bonds in tetrahydroisoquinolines and tetrahydro-β-carboline derivatives was investigated. C-C bond forming reactions proceeded with a range of nucleophiles (nitroalkane, enol silyl ether, indole, allylstannane, and tetrabutylammonium cyanide) under metal-free conditions and an oxygen atmosphere. Acetic acid caused a significant acceleration effect.

  DOI：

  10.1021/ol5018883

文献信息

• A recyclable self-assembled composite catalyst consisting of Fe₃O₄-rose bengal-layered double hydroxides for highly efficient visible light photocatalysis in water
  作者：Yuxing Huang、Zhuo Xin、Wenlong Yao、Qi Hu、Zhuohua Li、Liuqing Xiao、Bo Yang、Junmin Zhang

  DOI：10.1039/c8cc08130a

  日期：——

  The first case of a highly efficient layered double hydroxide (LDH) supported organic visible light photocatalyst is reported and it can catalyze various organic transformations with high efficiency in water under visible light irradiation.

  报道了第一种高效的层状双氢氧化物（LDH）负载的有机可见光光催化剂，它可以在可见光照射下高效催化水中的各种有机转化。
• A Robust Palladium(II)-Porphyrin Complex as Catalyst for Visible Light Induced Oxidative CH Functionalization
  作者：Wai-Pong To、Yungen Liu、Tai-Chu Lau、Chi-Ming Che

  DOI：10.1002/chem.201203774

  日期：2013.4.26

  A series of palladium(II)–porphyrin complexes that display dual emissions with lifetimes up to 437 μs have been synthesized. Among the four complexes, PdF20TPP is an efficient and robust catalyst for photoinduced oxidative CH functionalization by using oxygen as terminal oxidant. α‐Functionalized tertiary amines were obtained in good to excellent yields by light irradiation (λ>400 nm) of a mixture

  已经合成了一系列显示双发射且寿命高达437μs的钯（II）-卟啉配合物。在这四种络合物，PDF 20 TPP为光致氧化℃的高效且健壮的催化剂通过使用氧气作为氧化剂终端ħ官能化。通过对PdF 20 TPP的混合物进行光辐照（λ > 400 nm），可以得到高至极好产率的α-官能化叔胺，叔胺和亲核试剂（氰化物，硝基甲烷，丙二酸二甲酯，亚磷酸二乙酯和丙酮）在有氧条件下。可以类似地制备分子内环化胺化合物的四个实例。光化学反应前后的紫外可见吸收光谱比较表明，PdF 20 TPP具有很高的耐受性（回收率> 95％）。PdF 20 TPP的实际应用已通过使用低催化剂负载量（0.01 mol％）并以10 mmol规模进行的光化学反应得以揭示。该PDF 20 TPP催化剂可以优异的收率使光诱导的硫化物氧化为亚砜。机理研究表明，光催化通过单线态氧氧化进行。
• Donor-acceptor type [4+3] covalent organic frameworks: sub-stoichiometric synthesis and photocatalytic application
  作者：Qiaobo Liao、Wentao Xu、Xin Huang、Can Ke、Qi Zhang、Kai Xi、Jin Xie

  DOI：10.1007/s11426-019-9696-3

  日期：2020.5

  Three unprecedented 2D [4+3] covalent organic frameworks (TTCOF-1, TTCOF-2, and TTCOF-3) have been prepared by substoichiometric condensation of tetratopic and tritopic monomers, overcoming the limitations of the design rules of conventional topologies. By reticulating the tetraphenylethylene (TPE)-based and triazine-based moieties into COF frameworks, novel electron donor-acceptor (D-A) type structures

  通过四位和三位单体的亚化学计量缩合，已经克服了常规拓扑设计规则的局限性，制备了三种前所未有的2D [4 + 3]共价有机骨架（TTCOF-1，TTCOF-2和TTCOF-3）。通过将基于四苯乙烯（TPE）和基于三嗪的部分网状化为COF骨架，获得了新型的电子供体-受体（DA）型结构。这些TTCOF在可见光驱动的好氧C（sp 3）-H键官能化和芳基硼酸氧化中具有良好的光催化活性，收率高达94％。这可以加快具有新的结构和拓扑复杂性的COF的可能性，还可以扩展基于COF的光催化在合成化学中的应用。
• A Highly Efficient Gold-Catalyzed Oxidative CC Coupling from CH Bonds Using Air as Oxidant
  作者：Jin Xie、Huamin Li、Jiecong Zhou、Yixiang Cheng、Chengjian Zhu

  DOI：10.1002/anie.201107605

  日期：2012.1.27

  A breath of fresh air: The title reaction has been developed for the coupling of amines with nitroalkanes and different unmodified ketones using air as the sole oxidant under mild reaction conditions. The safe, convenient, and environmentally benign process, as well as the low catalyst loading, short reaction time, and good yields make this protocol very practical (see scheme).

  呼吸新鲜空气：在温和的反应条件下，使用空气作为唯一的氧化剂，已开发出标题反应，用于将胺与硝基烷烃和不同的未改性酮偶联。安全，方便且对环境无害的过程，以及催化剂用量低，反应时间短和产率高的特点，使该方案非常实用（请参阅方案）。
• Molecular Iodine Catalyzed Cross-Dehydrogenative Coupling Reaction between Two sp³ C–H Bonds Using Hydrogen Peroxide
  作者：Tomoya Nobuta、Norihiro Tada、Akitoshi Fujiya、Atsumasa Kariya、Tsuyoshi Miura、Akichika Itoh

  DOI：10.1021/ol303389t

  日期：2013.2.1

  A useful method for molecular iodine catalyzed oxidative C–C bond formation between tertiary amines and a carbon nucleophile using hydrogen peroxide as the terminal oxidant is reported. This is the first report of a molecular iodine catalyzed cross-dehydrogenative coupling (CDC) reaction between two sp3 C–H bonds.

  报道了一种有用的方法，该方法使用过氧化氢作为末端氧化剂，在叔胺和碳亲核试剂之间形成分子碘催化的氧化碳-碳键。这是两个sp 3 C–H键之间的分子碘催化的交叉脱氢偶联（CDC）反应的第一个报告。