(3,4-dihydroisoquinolin-2-ium-2-yl)(4-methoxybenzoyl)amide | 1311370-08-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: (3,4-dihydroisoquinolin-2-ium-2-yl)(4-methoxybenzoyl)amide
• 英文别名: (3,4-dihydroisoquinolinium-2-yl)(4-methoxybenzoyl)azanide；(1Z)-N-(3,4-dihydroisoquinolin-2-ium-2-yl)-4-methoxybenzenecarboximidate
• CAS: 1311370-08-7
• 化学式: C₁₇H₁₆N₂O₂
• 分子量: 280.326
• InChiKey: LPVZLMYJFDWBSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 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-dihydroisoquinolin-2-ium-2-yl)(4-methoxybenzoyl)amide 、 2,3-二苯基-2H-氮丙啶 以 水 为溶剂， 以87%的产率得到(8a,9-diphenyl-5,6,8a,9-tetrahydroazirino[2',1':3,4][1,2,4]triazolo[5,1-a]isoquinolin-8(10aH)-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  偶氮甲亚胺和2H-叠氮基的化学发散反应，用于合成含氮支架。

  摘要：

  研究了2H-叠氮基与C，N-环偶氮甲亚胺的无金属反应。获得了N-桥应变环稠合的三唑衍生物或1,2,4-三嗪衍生物，其化学选择性取决于偶氮甲碱偶极上的保护基。尽管苯甲酰基保护的起始原料可以接触到应变的多环化合物，但是对于甲苯磺酰基保护基来说，在消除亚磺酸的过程中裂解了甲苯磺酰基保护基时，会发生开环。1,2,4-三嗪可以制备成毫摩尔规模，并与空气作为氧化剂一起氧化形成相应的酮，这是一种在生物活性支架中可以发现的有趣的结构基序。

  DOI：

  10.1039/c9ob00740g
• 作为产物：
  描述：

  2-(2-溴乙基)苯甲醛 、 对甲氧基苯甲酰肼 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.25h， 以79%的产率得到(3,4-dihydroisoquinolin-2-ium-2-yl)(4-methoxybenzoyl)amide
  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

• 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。
• 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。
• 1,3-Dipolar Cycloadditions of 4-Acetoxy Allenoates: Access to 2,3-Dihydropyrazoles, 2,3-Dihydroisoxazoles, and Indolizines
  作者：Falin Li、Jiangfei Chen、Yading Hou、Yujie Li、Xin-Yan Wu、Xiaofeng Tong

  DOI：10.1021/acs.orglett.5b02724

  日期：2015.11.6

  The thermal 1,3-dipolar cycloadditions of 4-acetoxyallenoates 1 with various dipoles have been reported. When azomethine imines and nitrones are used as the 1,3-dipole partner, the corresponding reactions afford 2,3-dihydropyrazole and 2,3-dihydroisoxazole derivatives, respectively. These reactions might proceed via a thermal 1,3-dipolar cycloaddition and the subsequent elimination of HOAc. In addition

  已经报道了4-乙酰氧基脲酸酯1与各种偶极的热1，3-偶极环加成。当将甲亚胺亚胺和硝酮用作1,3-偶极伴侣时，相应的反应分别得到2,3-二氢吡唑和2,3-二氢异恶唑衍生物。这些反应可能通过热的1,3-偶极环加成反应和随后的HOAc消除反应进行。另外，脲基甲酸酯1与原位产生的甲亚胺基团良好反应，其中类似的环加成途径随后是氧化芳构化，以得到吲哚嗪衍生物。
• Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
  作者：Guipeng Feng、Guoyang Ma、Wenyan Chen、Shaohong Xu、Kaikai Wang、Shaoyan Wang

  DOI：10.3390/molecules26102969

  日期：——

  [3 + 2] A 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of

  [3 + 2]已实现C，N-环甲亚胺亚胺与烯丙基烷基酮的1,3-偶极环加成反应。反应在温和的条件下进行，并能耐受各种官能团。通常以良好的非对映选择性和对映选择性（高达> 25：1 dr，> 95％ee）构造一系列四氢异喹啉衍生物。此外，事先通过使用量子电子圆二色性计算和ECD光谱法确定了产物的绝对构型。
• Palladium-Catalyzed Asymmetric Tandem [3+2] Cycloaddition/Allylation Reaction of Methylene-Trimethylenemethane: Access to Chiral Tricyclic Dinitrogen-Fused Heterocycles
  作者：Biming Mao、Yi Xu、Yuehua Chen、Jipan Dong、Junya Zhang、Kejia Gu、Bing Zheng、Hongchao Guo

  DOI：10.1021/acs.orglett.9b01064

  日期：2019.6.21

  A palladium-catalyzed asymmetric tandem [3+2] cycloaddition/allylation of methylene-trimethylenemethane is presented, providing the functionalized chiral hexahydropyrazolo[5,1-a]isoquinoline derivatives in high yields with good to excellent enantioselectivities and moderate to good E:Z ratios. In the one-pot sequential tandem reactions/hydroxylation, (E)-allylic alcohol products were obtained in good

  提出了钯催化的亚甲基三亚甲基甲烷的不对称串联[3 + 2]环加成/烯丙基化反应，以高收率提供了功能化的手性六氢吡唑并[5,1- a ]异喹啉衍生物，具有良好的至优异的对映选择性和中等至良好的E：Z比率。在一锅顺序串联反应/羟基化中，以高收率获得具有优异对映选择性的（E）-烯丙醇产物。