ethyl 3-methyl-2H-isoindole-1-carboxylate | 1111311-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: ethyl 3-methyl-2H-isoindole-1-carboxylate
• CAS: 1111311-17-1
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: OAQRWPDBRBXNBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氘代苯 在 aluminum (III) chloride 、 silver tetrafluoroborate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 三氯异氰尿酸 、 甲酸铵 、 sodium acetate 作用下， 以 甲醇 、 二硫化碳 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 28.0h， 生成 ethyl 3-methyl-2H-isoindole-1-carboxylate
  参考文献：
  名称：

  Rh(III)-Catalyzed Coupling of N-Chloroimines with α-Diazo-α-phosphonoacetates for the Synthesis of 2H-Isoindoles

  摘要：

  We report herein the first use of N-chloroimines as effective synthons for directed C-H functionalization. Rh(III)-catalyzed coupling of N-chloroimines with α-diazo-α-phosphonoacetates allows for efficient dechlorinative/dephosphonative access to 2H-isoindoles. Further deesterification under Ni(II) catalysis enables the complete elimination of reactivity-assisting groups and full exposure of reactivity of C3 and N2 ring atoms for attaching structurally distinct appendages.

  DOI：

  10.1021/acs.orglett.9b02501

文献信息

• Synthesis of Isoindoles from Intramolecular Condensation of Benzyl Azides with α-Aryldiazoesters
  作者：Jing Zhu、Rui Li、Yan Su、Peiming Gu

  DOI：10.1021/acs.joc.8b03180

  日期：2019.5.3

  Rh-catalyzed intramolecular condensation of the benzyl azides with α-aryldiazoesters was explored. The reaction proceeded through the nucleophilic attack of the organic azide onto a rhodium carbenoid, while releasing nitrogen gas, affording the α-imino esters as the primary product. Tautomerization of the imino esters efficiently gave 13 desired isoindoles with good to excellent yields.

  探索了Rh催化的叠氮化物与α-芳基重氮酯的分子内缩合。反应通过有机叠氮化物对铑类胡萝卜素的亲核攻击而进行，同时释放氮气，得到α-亚氨基酯作为主要产物。亚氨基酯的互变异构有效地以良好至优异的产率得到13种所需的异吲哚。
• Synthesis of Isoindoles via 1,3-Dipolar Cycloaddition of α-Azido Carbonyl Compounds onto Intramolecular Alkenes and Their Conversion into Substituted Aromatic Hydrocarbons
  作者：Shunsuke Chiba、Benny Tong、Benjamin Hui、Sze Chua

  DOI：10.1055/s-0030-1260221

  日期：2011.11

  α-Azido carbonyl compounds bearing a 2-alkenylaryl moiety in the α-position are found to be promising precursors in the synthesis of isoindoles via 1,3-dipolar cycloaddition of azides to alkenes. Applications of these isoindoles in the preparation of 1,2,3,4-tetrasubstituted naphthalene and 9,10-disubstituted anthracene derivatives were developed via [4+2]-cycloaddition reactions of isoindoles with

  发现在α-位置带有2-链烯基芳基部分的α-叠氮羰基化合物是通过叠氮化物与烯烃的1，3-偶极环加成合成异吲哚的有希望的前体。这些异吲哚在制备1,2,3,4-四取代的萘和9,10-二取代的蒽衍生物中的应用分别是通过异吲哚与乙酰二羧酸二甲酯和苯并炔的[4 + 2]-环加成反应，然后进行脱氨基反应而开发的芳香化。 异吲哚-有机叠氮化物-1,3-偶极环加成-芳烃-苯并
• Orthogonal Synthesis of Isoindole and Isoquinoline Derivatives from Organic Azides
  作者：Benjamin Wei-Qiang Hui、Shunsuke Chiba

  DOI：10.1021/ol802816k

  日期：2009.2.5

  alpha-Azido carbonyl compounds bearing a 2-alkenylaryl moiety at the alpha-position are found to be promising precursors for synthesis of isoindole and isoquinoline derivatives via 1,3-dipolar cycloaddition of azides onto alkenes and 6 pi-electrocyclization of N-H imine intermediates, respectively.
• Rh(III)-Catalyzed Coupling of <i>N</i>-Chloroimines with α-Diazo-α-phosphonoacetates for the Synthesis of 2<i>H</i>-Isoindoles
  作者：Bing Qi、Lei Li、Qi Wang、Wenjing Zhang、Lili Fang、Jin Zhu

  DOI：10.1021/acs.orglett.9b02501

  日期：2019.9.6

  We report herein the first use of N-chloroimines as effective synthons for directed C-H functionalization. Rh(III)-catalyzed coupling of N-chloroimines with α-diazo-α-phosphonoacetates allows for efficient dechlorinative/dephosphonative access to 2H-isoindoles. Further deesterification under Ni(II) catalysis enables the complete elimination of reactivity-assisting groups and full exposure of reactivity of C3 and N2 ring atoms for attaching structurally distinct appendages.