(3,4-dihydroisoquinolinium-2-yl)(4-methylbenzoyl)azanide | 1311370-07-6

• 英文名称: (3,4-dihydroisoquinolinium-2-yl)(4-methylbenzoyl)azanide
• CAS: 1311370-07-6
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: NCMRNVHBOFGKBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  (3,4-dihydroisoquinolinium-2-yl)(4-methylbenzoyl)azanide 在 六甲基磷酰三胺 、 dimethylphenyl sulfonium tetrafluoroborate 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以87%的产率得到3-(p-tolyl)-6,7-dihydro-1H-1,5-methanobenzo[g][1,3,4]oxadiazonine
  参考文献：
  名称：

  Ring Enlargement Reaction of C,N-Cyclic-N′-acyl Azomethine Imines with Sulfonium Ylide: An Efficient Synthesis of 3-Benzazepine Derivatives

  摘要：

  Highly efficient formation of 3-benzazepine derivatives has been achieved, based on the ring expansion reaction of C,N-cyclic-N'-acyl azomethine imines with sulfonium ylide generated in situ from the corresponding sulfonium salt. The reactions proceeded smoothly to afford the tricyclic 3-benzazepine derivatives in good to high yields. A wide range of C,N-cyclic N'-acyl azomethine imines were applicable to this reaction.

  DOI：

  10.1021/ol502347n
• 作为产物：
  描述：

  2-(2-溴乙基)苯甲醛 、 对甲苯甲酰肼 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.25h， 以72%的产率得到(3,4-dihydroisoquinolinium-2-yl)(4-methylbenzoyl)azanide
  参考文献：
  名称：

  Stable azomethine imines having a 3,4-dihydroisoquinoline fragment and their cycloaddition to N-arylmaleimides

  摘要：

  Aroylation of 5,6,8,8a,13,14,16,16a-octahydro[1,2,4,5]tetrazino[6,1-a:3,4-a']diisoquinoline or 1,3,4,8b-tetrahydro[1,2]diazireno[3,1-a]isoquinoline, as well as reactions of 2-(2-bromoethyl)benzaldehyde with aroylhydrazines followed by treatment with triethylamine, led to the formation of stable azomethine imines, aroyl(3,4-dihydroisoquinolinium-2-yl)azanides. 1,3-Dipolar cycloaddition of the latter to N-mesitylmaleimide was stereoselective: the ratio of the trans- and cis-adducts was similar to(3-7): 1, the former prevailing. The reactions with N-arylmaleimides having no ortho-substituents in the aryl group gave the corresponding cis-adducts as the major products [trans/cis ratio similar to 1: (2.5-10)].

  DOI：

  10.1134/s1070428011040129

文献信息

• [5 + 1] Cycloaddition of <i>C,N</i>-Cyclic <i>N</i>′-Acyl Azomethine Imines with Isocyanides
  作者：Takahiro Soeta、Kaname Tamura、Yutaka Ukaji

  DOI：10.1021/ol2034542

  日期：2012.3.2

  A catalyst-free [5 + 1] cycloaddition reaction between isocyanides and C,N-cyclic N′-acyl azomethine imines as the “isocyanophile” leading to novel heterocycles has been developed. These reactions proceeded quickly and cleanly to afford the corresponding imin-1,3,4-oxadiazin-6-one derivatives in high to excellent yields. A wide range of C,N-cyclic N′-acyl azomethine imines and isocyanides were applicable

  已开发出异氰酸酯与作为新异杂环的“异氰酸酯”的C，N-环N'-酰基偶氮甲亚胺亚胺之间的无催化剂[5 +1]环加成反应。这些反应快速而干净地进行，以高到极好的收率得到相应的亚胺-1,3,4-恶二嗪-6-一衍生物。各种各样的C，N-环N'-酰基偶氮甲亚胺和异氰酸酯可用于该反应。
• A three-component reaction of C,N-cyclic N′-acyl azomethine imines, isocyanides, and azide compounds: effective synthesis of 1,5-disubstituted tetrazoles with tetrahydroisoquinoline skeletons
  作者：Takahiro Soeta、Kaname Tamura、Shuhei Fujinami、Yutaka Ukaji

  DOI：10.1039/c3ob27297d

  日期：——

  A multicomponent reaction of isocyanides and C,N-cyclic N′-acyl azomethine imines in the presence of TMSCl and NaN3 leads to tetrazole derivatives. These reactions proceeded cleanly to afford the corresponding 1,5-disubstituted tetrazoles containing a tetrahydroisoquinoline skeleton in high to excellent yields.

  在TMSCl和NaN3的存在下，异氰化物与C,N-环状N'-酰基偶氮甲亚胺的多元反应可得到四唑衍生物。这些反应顺利进行，以高水平至极佳的产率得到了含有四氢异喹啉骨架的1,5-二取代四唑。
• Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines
  作者：Biming Mao、Junya Zhang、Yi Xu、Zhengyang Yan、Wei Wang、Yongjun Wu、Changqing Sun、Bing Zheng、Hongchao Guo

  DOI：10.1039/c9cc06670e

  日期：——

  with azomethine imines has successfully been developed under mild reaction conditions, affording biologically interesting tetrahydropyrazoloisoquinoline derivatives in high to excellent yields and with excellent stereoselectivity. The reaction follows a tandem [3+2] cycloaddition/allylation/elimination of AcOH pathway. Allenyl carbinol acetates also reacted well with in situ generated azomethine imine

  在本文中，成功开发了在温和的反应条件下钯催化的[3 + 2]烯丙乙酸乙酸酯与偶氮甲亚胺的环化反应，提供了生物学上令人感兴趣的四氢吡唑并异喹啉衍生物，具有高到极好的收率，并且具有出色的立体选择性。反应遵循串联的[3 + 2]环加成/烯丙基化/消除AcOH途径。烯丙基甲醇乙酸酯在相似的反应路径下，在Ag（I）/ Pd（0）催化剂的共催化下，还可以与原位生成的甲亚胺亚胺充分反应。
• 1,3‐Dipolar Cycloaddition between Dehydroalanines and C,N‐Cyclic Azomethine Imines: Application to Late‐Stage Peptide Modification
  作者：Guangjun Bao、Peng Wang、Guofeng Li、Changjun Yu、Yiping Li、Yuyang Liu、Zeyuan He、Tiantian Zhao、Jing Rao、Junqiu Xie、Liang Hong、Wangsheng Sun、Rui Wang

  DOI：10.1002/anie.202012523

  日期：2021.3

  between bi‐ or mono‐N‐protected Dha and C,N‐cyclic azomethine imines, which afford various quaternary amino acids with diverse scaffolds, is disclosed. Specifically, normal‐electron‐demand 1,3‐DC reaction occurs between bi‐N‐protected Dha and C,N‐cyclic azomethine imines, while inverse‐electron‐demand 1,3‐DC reaction occurs between mono‐N‐protected Dha and C,N‐cyclic azomethine imines. Above all, the

  非催化，温和且易于操作的保护基在双或单N-保护的Dha与C，N-环偶氮甲亚胺之间切换1,3-偶极环加成（1,3-DC）公开了具有各种支架的各种季氨基酸。具体来说，在双N保护的Dha与C，N环甲亚胺亚胺之间发生正常的电子需求1,3-DC反应，而在单N保护的Dha之间发生反电子需求的1,3-DC反应。和C，N-环偶氮甲亚胺。最重要的是，该反应可以在目标位置具有Dha残基的肽与C，N-环偶氮甲亚胺在均相和SPPS树脂上进行。它为后期肽修饰，标记和肽-药物结合提供了一个新的工具包。为了阐明反应的高区域选择性，
• N-Heterocyclic carbene-catalyzed [2+3] cyclocondensation of α-chloroaldehydes with azomethine imines
  作者：Zhong-Hua Gao、Xiang-Yu Chen、Jin-Tang Cheng、Wei-Lin Liao、Song Ye

  DOI：10.1039/c5cc01238d

  日期：——

  The N-heterocyclic carbene-catalyzed enantioselective [2+3] cyclocondensation of α-chloroaldehydes with azomethine imines was developed to give the corresponding pyrazolidinones in good yields with excellent enantioselectivities.

  N-杂环卡宾催化的α-氯醛与偶氮甲醛亚胺的对映选择性[2+3]环缩合反应已经发展，能够以良好产率和优异对映选择性得到相应的吡唑啉酮。