benzyl 1-(2-oxo-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate | 1428485-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 1-(2-oxo-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
• 英文别名: 2-benzylcarboxy-1-(2-oxo-2-phenylethyl)-3,4-dihydroisoquinoline；benzyl 1-phenacyl-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 1428485-05-5
• 化学式: C₂₅H₂₃NO₃
• 分子量: 385.463
• InChiKey: JNRSZTAUQMHWLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 1-(2-oxo-2-phenylethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 5.0h， 以93%的产率得到1-(2-苯基乙基)-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline by sodium persulfate

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2014.03.094
• 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 5.0h， 生成 benzyl 1-(2-oxo-2-phenylethyl)-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。
• Enolizable Carbonyls and <i>N</i> ,<i>O</i> -Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes
  作者：Bahria Touati、Abderrahman El Bouakher、Catherine Taillier、Raja Ben Othman、Malika Trabelsi-Ayadi、Sylvain Antoniotti、Elisabet Duñach、Vincent Dalla

  DOI：10.1002/chem.201504772

  日期：2016.4.18

  carbonyl donors, that is, ketones and aldehydes with unbiased N,O‐acetals, is described. Sn(NTf2)4 is an optimal catalyst to promote this challenging transformation at low loading and the reaction shows promising scope. A comprehensive and rational evaluation of this reaction has led to the establishment of an empirical scale of nucleophilic reactivity for a broad set of ketones that should be helpful

  描述了羰基供体的高效催化室温直接α-酰胺基烷基化反应，即具有无偏N，O-乙缩醛的酮和醛。Sn（NTf 2）4是在低负荷下促进这一具有挑战性的转变的最佳催化剂，该反应具有广阔的前景。对该反应进行了全面而合理的评估，已建立了一套广泛的酮亲核反应性的经验规模，这对羰基α-官能化方法的合成设计和开发应有所帮助。
• Mechanochemical Oxidative Mannich Reaction: Evaluation of Chemical and Mechanical Parameters for the Mild and Chemoselective Coupling of<i>N</i>-<i>tert</i>-butoxycarbonyltetrahydroquinolines and Ketones
  作者：Jing-Bo Yu、Gang Peng、Zhi-Jiang Jiang、Zi-Kun Hong、Wei-Ke Su

  DOI：10.1002/ejoc.201600987

  日期：2016.11

  A mechanochemical oxidative Mannich reaction of N-tert-butoxycarbonyl (Boc) tetrahydroquinolines and ketones was successfully developed under solvent-free ball-milling conditions. The reaction afforded the desired coupling products in satisfactory yields under mild and tractable oxidative conditions. Side reactions such as deprotection of the Boc group were prevented by carefully adjusting the milling

  在无溶剂球磨条件下成功开发了 N-叔丁氧基羰基 (Boc) 四氢喹啉和酮的机械化学氧化曼尼希反应。该反应在温和且易处理的氧化条件下以令人满意的产率提供了所需的偶联产物。通过仔细调整研磨参数，包括研磨频率、时间、研磨球填充度、研磨球尺寸和研磨助剂，防止了 Boc 基团脱保护等副反应。对范围的进一步检查表明，该反应体系也可以应用于 N-苄氧羰基和 N-芳基底物，以中等至良好的收率提供相应的产物。
• Manganese Dioxide–Methanesulfonic Acid Promoted Direct Dehydrogenative Alkylation of sp³ C–H Bonds Adjacent to a Heteroatom
  作者：Xigong Liu、Bin Sun、Zhiyu Xie、Xiaojun Qin、Lei Liu、Hongxiang Lou

  DOI：10.1021/jo4000674

  日期：2013.4.5

  A manganese dioxide (MnO2)-methanesulfonic acid (CH3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation. The alkylation proceeds smoothly under air atmosphere to afford the corresponding products in good to excellent yields (53-87%). The employment of the combination of MnO2 and CH3SO3H is attractive on the basis of economical and environmental issues.