ethyl 2-(3-methyl-2-(pyrimidin-2-yl)phenyl)acetate | 1436430-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(3-methyl-2-(pyrimidin-2-yl)phenyl)acetate
• 英文别名: Ethyl 2-(3-methyl-2-pyrimidin-2-ylphenyl)acetate；ethyl 2-(3-methyl-2-pyrimidin-2-ylphenyl)acetate
• CAS: 1436430-75-9
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: FPOLFDBGOGGFMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-methyl-2-(pyrimidin-2-yl)phenyl)acetate 在 对甲苯磺酰叠氮 、 dicobalt octacarbonyl 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 ethyl 11-methyl-6-oxo-6H-pyrimido[2,1-a]isoquinoline-7-carboxylate
  参考文献：
  名称：

  Cobalt-Catalyzed Carbonylative Cyclization of Pyridinyl Diazoacetates for the Synthesis of Pyridoisoquinolinones

  摘要：

  Dicobalt octacarbonyl-catalyzed carbonylative cyclization of pyridinyl diazoacetates is developed for the synthesis of pyridoisoquinolinones under mild conditions (room temperature) in a carbon monoxide atmosphere. Moreover, a synthetic method for various pyridoisoquinolinones from ethylp-yridinyl aryl acetates is demonstrated through diazotization using TsN3 and DBU followed by Co-catalyzed carbonylation to generate ketene intermediates, which can subsequently undergo intramolecular cyclization under mild conditions in a carbon monoxide atmosphere in a semi-one-pot fashion.

  DOI：

  10.1021/acs.orglett.5b03340
• 作为产物：
  描述：

  5-重氮米氏酸(=5-重氮-2,2-二甲基-1,3-二氧杂环己烷-4,6-二酮) 、 2-(2-methylphenyl)pyrimidine 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以84%的产率得到ethyl 2-(3-methyl-2-(pyrimidin-2-yl)phenyl)acetate
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Azacycle-Directed Intermolecular Insertion of Arene C–H Bonds into α-Diazocarbonyl Compounds

  摘要：

  Cp*Rh(III)-catalyzed intermolecular C C couplings between activated alpha-diazocarbonyl compounds and arenes bearing a range of azacyclic directing groups have been achieved. This catalytic alkylation reaction operates under mild conditions with good functional group tolerance.

  DOI：

  10.1021/jo400572h

文献信息

• Synthesis of Pyridoisoindoles through Diazotization Followed by Intramolecular Cyclization from Pyridinylarylacetates in One Pot
  作者：Cheol-Eui Kim、Yonghyeon Baek、Sung Hong Kim、Phil Ho Lee

  DOI：10.1002/adsc.201500433

  日期：2015.9.14

  method for a variety of pyridoisoindoles from pyridinylarylacetates has been developed through diazotization using 4‐methylbenzenesulfonyl azide and 1,8‐diazabicyclo[5.4.0]undec‐7‐ene followed by intramolecular cyclization via elimination of a nitrogen molecule under copper(II) trifluoromethanesulfonate‐catalyzed conditions in a one‐pot process. The intramolecular cyclization also took place efficiently

  通过使用4-甲基苯磺酰基叠氮化物和1,8-二氮杂双环[5.4.0]十一碳-7-烯进行重氮化，然后通过消除铜下的氮分子进行分子内环化，已开发出一种强大的合成方法，用于从吡啶基芳基乙酸酯中合成各种吡啶基异吲哚。II）一锅法中三氟甲磺酸盐催化的条件。在无金属条件或催化条件[1.0 mol％三氟甲磺酸铜（II）铜，25°C]下，重氮底物也有效地进行了分子内环化反应，以良好的产率获得了吡啶异吲哚。
• 신규한 피리도아이소인돌 유도체의 제조방법
  申请人：KNU-Industry Cooperation Foundation 강원대학교산학협력단(220040088571) BRN ▼221-82-10213

  公开号：KR20170109709A

  公开（公告）日：2017-10-10

  본 발명은 약학, 천연물, 형광 물질, 염색 물질과 같은 다양한 분야에서 사용되는 주요 골격 구조로 이용될 수 있는 피리도아이소인돌 유도체의 제조방법에 관한 것으로, 다양한 친핵체와 반응 할 수 있는 카벤 유도체를 이용하여 다이아조아세테이트로부터 구리촉매 존재 하에 또는 구리촉매 없이 가열만을 통해 효과적이고 보다 용이하게 피리도아이소인돌 유도체의 제조방법을 제공한다. 또한 아세테이트 유도체에 염기성 촉매, 아지드 유도체를 사용하여 diazotization을 진행한 후 Cu(OTf) 촉매하에 질소의 제거반응을 통한 분자내 고리화 반응을 one-pot으로 진행 시켜 피리도인돌유도체의 효율적인 제조방법을 제공한다.

  本发明涉及一种制备可用作药学、天然物、荧光物质、染料等多个领域的主要骨架结构的吡啶并异吲哚衍生物的制备方法，利用多种亲核试剂与卡宾衍生物反应，通过在铜催化下或仅通过加热而无需铜催化的条件下，从二氮基乙酸酯中有效且更容易地制备吡啶并异吲哚衍生物。此外，本发明还提供了一种高效的制备方法，通过使用碱性催化剂和叠氮化合物对乙酸酯衍生物进行重氮化反应，然后在Cu(OTf)催化下进行分子内环化反应，以一步完成吡啶并异吲哚衍生物的制备。
• Rhodium(III)-Catalyzed Azacycle-Directed Intermolecular Insertion of Arene C–H Bonds into α-Diazocarbonyl Compounds
  作者：Xinzhang Yu、Songjie Yu、Jian Xiao、Boshun Wan、Xingwei Li

  DOI：10.1021/jo400572h

  日期：2013.6.7

  Cp*Rh(III)-catalyzed intermolecular C C couplings between activated alpha-diazocarbonyl compounds and arenes bearing a range of azacyclic directing groups have been achieved. This catalytic alkylation reaction operates under mild conditions with good functional group tolerance.
• Cobalt-Catalyzed Carbonylative Cyclization of Pyridinyl Diazoacetates for the Synthesis of Pyridoisoquinolinones
  作者：Yonghyeon Baek、Sunghwa Kim、Bongkeun Jeon、Phil Ho Lee

  DOI：10.1021/acs.orglett.5b03340

  日期：2016.1.4

  Dicobalt octacarbonyl-catalyzed carbonylative cyclization of pyridinyl diazoacetates is developed for the synthesis of pyridoisoquinolinones under mild conditions (room temperature) in a carbon monoxide atmosphere. Moreover, a synthetic method for various pyridoisoquinolinones from ethylp-yridinyl aryl acetates is demonstrated through diazotization using TsN3 and DBU followed by Co-catalyzed carbonylation to generate ketene intermediates, which can subsequently undergo intramolecular cyclization under mild conditions in a carbon monoxide atmosphere in a semi-one-pot fashion.