α-(2-methylphenyl)isocyanoethanoic acid methyl ester | 1452589-00-2

• 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: α-(2-methylphenyl)isocyanoethanoic acid methyl ester
• 英文别名: Methyl 2-isocyano-2-(2-methylphenyl)acetate
• CAS: 1452589-00-2
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: VLSKJUJERCTBEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-苯硫基-吡咯啉-2,5-二酮 、 α-(2-methylphenyl)isocyanoethanoic acid methyl ester 在 三乙烯二胺 、 silver(I) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 0.4h， 以91%的产率得到methyl 2-(2-methylphenyl)-2-isocyano-2-(phenylthio)acetate
  参考文献：
  名称：

  DABCO/AgOAc cooperatively catalyzed α-sulfenylation of isocyanoacetates with N-(sulfanyl)succinimides

  摘要：

  The first organo/metal cooperatively catalyzed alpha-sulfenylation of isocyanoacetates with N-(sulfanyl)succinimides has been developed. The reaction condition was suitable to alpha-aryl and alkyl-substituted iso-cyanoactates as well as N-(arylthio)succinimides, affording the corresponding products with high yields (90-96%). Preliminary asymmetric organocatalysis has also been evaluated. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2019.01.050

文献信息

• Asymmetric Formal [3+2] Cycloaddition Reaction of α-Aryl Isocyanoesters with<i>N</i>-Aryl Maleimides by Bifunctional Cinchona Alkaloids-Based Squaramide/AgSbF₆Cooperative Catalysis
  作者：Mei-Xin Zhao、Deng-Ke Wei、Fei-Hu Ji、Xiao-Li Zhao、Min Shi

  DOI：10.1002/asia.201200686

  日期：2012.12

  better to be cooperative: A highly diastereo‐ and enantioselective asymmetric [3+2] cycloaddition reaction of α‐aryl isocyanoacetates with N‐aryl maleimides through cooperative catalysis of cinchona alkaloid‐derived squaramide/AgSbF6 was developed. A wide range of optically active, substituted 1,3a,4,5,6,6a‐hexahydropyrrolo[3,4‐c] pyrrole derivatives was obtained in high yields (up to 98 %), high diastereoselectivities

  最好是协同作用：通过金鸡纳生物碱衍生的方酸酰胺/ AgSbF 6的协同催化，开发了α-芳基异氰基乙酸酯与N-芳基马来酰亚胺的高度非对映体和对映选择性不对称[3 + 2]环加成反应。以高收率（高达98％），高非对映选择性（> 20：1 dr ），并且在温和的反应条件下对映体的选择性良好（高达ee的92％）。
• Diastereo- and enantioselective Mannich/cyclization cascade reaction of isocyanoacetates with cyclic sulfamide ketimines by cinchona alkaloid squaramide/AgOAc cooperative catalysis
  作者：Mei-Xin Zhao、Zhi-Wen Dong、Guang-Yu Zhu、Xiao-Li Zhao、Min Shi

  DOI：10.1039/c8ob01090k

  日期：——

  an efficient diastereo- and enantioselective Mannich/cyclization cascade reaction of α-substituted isocyanoacetates with 4-aryl-3-carbonyl-1,2,5-thiadiazole-1,1-dioxide type cyclic sulfamide ketimines cooperatively catalyzed by cinchona alkaloid-derived squaramide and AgOAc. The corresponding optically active 2,3,3a,4-tetrahydroimidazo[1,5-b][1,2,5]thiadiazole-1,1-dioxide derivatives were obtained

  我们已经开发了由金鸡纳生物碱协同催化的α-取代异氰基乙酸酯与4-芳基-3-羰基-1,2,5-噻二唑-1,1-二氧化物型环硫酰胺酮亚胺的高效非对映和对映选择性曼尼希/环化级联反应衍生的方胺和AgOAc。获得了相应的旋光性2,3,3a，4-四氢咪唑并[1,5- b ] [1,2,5]噻二唑-1,1-二氧化物衍生物，收率极高（高达99％）立体选择性（高达> 20：1 dr，高达94％ee）。