benzyl 1-(4-methoxyphenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1449307-89-4

• 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: benzyl 1-(4-methoxyphenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
• 英文别名: benzyl 1-(4-methoxyphenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1449307-89-4
• 化学式: C₂₄H₂₃NO₃
• 分子量: 373.452
• InChiKey: LCSFLNIPDXAHTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 1-(4-methoxyphenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline 、 (S)-1-(4-methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Organocatalytic Asymmetric C–H Vinylation and Arylation of N-Acyl Tetrahydroisoquinolines

  摘要：

  The first organocatalytic enantioselective oxidative C-H functionalization of N-acyl tetrahydroisoquinolines with vinyl and aryl boronates promoted by a chiral Bronsted acid is described. This metal-free process tolerates a wide range of electronically varied N-acyl tetrahydroisoquinolines and structurally diverse boronates with good to excellent enantioselectivities.

  DOI：

  10.1021/acs.orglett.5b00909
• 作为产物：
  描述：

  benzyl 3,4-dihydroisoquinoline-2(1H)-carboxylate 在 甲烷磺酸 、 溶剂黄146 作用下， 以 癸烷 为溶剂， 反应 26.0h， 生成 benzyl 1-(4-methoxyphenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  N-保护的四氢异喹啉通过中间过氧化物的布朗斯台德酸催化 CH 官能化

  摘要：

  N-保护的四氢异喹啉的有机催化氧化合成通过中间过氧化物的 C-H 官能化进行描述。过氧化物是在无金属热条件下由叔丁基过氧化氢合成的，并通过布朗斯台德酸催化取代转化为最终产物。亲核试剂的范围被详细研究并证明是广泛的；也可以实现偶联产物的 N-脱保护。

  DOI：

  10.1002/ejoc.201201527

文献信息

• Practical Metal-Free C(sp³)H Functionalization: Construction of Structurally Diverse α-Substituted<i>N</i>-Benzyl and<i>N</i>-Allyl Carbamates
  作者：Zhiyu Xie、Lei Liu、Wenfang Chen、Hongbo Zheng、Qingqing Xu、Huiqing Yuan、Hongxiang Lou

  DOI：10.1002/anie.201310193

  日期：2014.4.7

  is a practical and universal CH functionalization of readily removable N‐benzyl and N‐allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal‐free reaction has an excellent functional‐group tolerance, and displays a broad scope with respect to both N‐carbamates and nucleophile partners (a variety of organoboranes and CH compounds). The synthetic utility

  描述了一种实用的和普遍Ç 易于除去h的官能ñ -苄基和Ñ -烯丙基氨基甲酸酯，在环境温度下的宽范围的亲核试剂通过pH促进3 CClO 4。无金属反应具有出色的官能团耐受性，并且在N-氨基甲酸酯和亲核试剂（各种有机硼烷和CH化合物）方面都具有广阔的应用范围。展示了目标以及面向多样性的综合中的综合效用。
• Transition-Metal-Free Oxidative Cross-Coupling of Triorganoindium Reagents with Tetrahydroisoquinolines
  作者：José M. Gil-Negrete、José Pérez Sestelo、Luis A. Sarandeses

  DOI：10.1021/acs.joc.9b00928

  日期：2019.8.2

  proceeds in good yields at rt using 50 mol % R3In with a variety of organic groups. 1H NMR studies show the generation of an iminium ion intermediate, supporting a two-step mechanism based on THIQ oxidation and R3In nucleophilic addition. This reaction was applied to the synthesis of the alkaloid nuciferine in three steps.

  三有机铟试剂（R 3 In）在作为氧化剂的Ph 3 CBF 4存在下与四氢异喹啉（THIQ）反应，得到1-取代的THIQ。使用具有各种有机基团的50 mol％R 3 In，该反应在室温下以良好的产率进行。1 H NMR研究表明生成了亚胺离子中间体，该中间体支持基于THIQ氧化和亲核加成中的R 3的两步机理。通过三个步骤将该反应应用于生物碱生物碱的合成。
• A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline by sodium persulfate
  作者：Wenfang Chen、Hongbo Zheng、Xinhui Pan、Zhiyu Xie、Xin Zan、Bin Sun、Lei Liu、Hongxiang Lou

  DOI：10.1016/j.tetlet.2014.03.094

  日期：2014.4

  A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline with a variety of C-H nucleophiles mediated by Na2S2O8 is developed. The reaction proceeds smoothly to give the coupled product in up to 83% yields. The nucleophile scope is broad, including simple ketones, aldehydes, and aryl rings. The carbamoyl protecting group can be readily removed under mild condition. The use of Na2S2O8 as the sole reagent for the CDC reaction is attractive based on economical and environmental factors. (C) 2014 Elsevier Ltd. All rights reserved.
• Brønsted Acid Catalyzed C-H Functionalization of<i>N</i>-Protected Tetrahydroisoquinolines via Intermediate Peroxides
  作者：Bertrand Schweitzer-Chaput、Martin Klussmann

  DOI：10.1002/ejoc.201201527

  日期：2013.2

  An organocatalytic oxidative synthesis of N-protected tetrahydroisoquinolines is described by C–H functionalization via intermediate peroxides. The peroxides were synthesized from tert-butylhydroperoxide under metal-free thermal conditions and were converted into the final products by Bronsted acid catalyzed substitution. The nucleophile scope was investigated in detail and proved to be broad; N-deprotection

  N-保护的四氢异喹啉的有机催化氧化合成通过中间过氧化物的 C-H 官能化进行描述。过氧化物是在无金属热条件下由叔丁基过氧化氢合成的，并通过布朗斯台德酸催化取代转化为最终产物。亲核试剂的范围被详细研究并证明是广泛的；也可以实现偶联产物的 N-脱保护。
• Organocatalytic Asymmetric C–H Vinylation and Arylation of <i>N</i>-Acyl Tetrahydroisoquinolines
  作者：Xigong Liu、Shutao Sun、Zhilin Meng、Hongxiang Lou、Lei Liu

  DOI：10.1021/acs.orglett.5b00909

  日期：2015.5.15

  The first organocatalytic enantioselective oxidative C-H functionalization of N-acyl tetrahydroisoquinolines with vinyl and aryl boronates promoted by a chiral Bronsted acid is described. This metal-free process tolerates a wide range of electronically varied N-acyl tetrahydroisoquinolines and structurally diverse boronates with good to excellent enantioselectivities.