α-(3-fluorophenyl)isocyanoethanoic acid methyl ester | 1452588-96-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: α-(3-fluorophenyl)isocyanoethanoic acid methyl ester
• 英文别名: Methyl 2-(3-fluorophenyl)-2-isocyanoacetate
• CAS: 1452588-96-3
• 化学式: C₁₀H₈FNO₂
• 分子量: 193.177
• InChiKey: XRBMZIXMZKLASK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苯硫基-吡咯啉-2,5-二酮 、 α-(3-fluorophenyl)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 0.2h， 以92%的产率得到methyl 2-(3-fluorophenyl)-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

• Chiral squaramides catalyzed diastereo- and enantioselective Michael addition of α-substituted isocyanoacetates to N-aryl maleimides
  作者：Mei-Xin Zhao、Fei-Hu Ji、Deng-Ke Wei、Min Shi

  DOI：10.1016/j.tet.2013.09.084

  日期：2013.12

  An efficient diastereo- and enantioselective Michael addition of α-substituted isocyanoacetates to N-aryl maleimides catalyzed by quinine or cyclohexane-1,2-diamine derived squaramide catalysts has been disclosed, affording the corresponding adducts in good yields (up to 99%), high diastereoselectivities (up to >20:1 dr) and good to excellent enantioselectivities (up to 94% ee) under mild conditions

  已经公开了由奎宁或环己烷-1，2-二胺衍生的方酰胺催化剂催化的α-取代的异氰基乙酸酯向N-芳基马来酰亚胺的高效非对映和对映选择性迈克尔加成反应，可提供相应的加合物，收率高（高达99％），非对映选择性高（高达> 20：1 dr），在温和条件下良好至优异的对映选择性（高达94％ee）。
• Cinchona alkaloid thiourea mediated asymmetric Mannich reaction of isocyanoacetates with isatin-derived ketimines and subsequent cyclization: enantioselective synthesis of spirooxindole imidazolines
  作者：Mei-Xin Zhao、Lei Jing、Hao Zhou、Min Shi

  DOI：10.1039/c5ra17075c

  日期：——

  The organocatalyzed asymmetric Mannich reaction of isocyanoacetates with isatin ketimines and subsequent cyclization were developed, leading to spirooxindole imidazolines in high yields and excellent stereoselectivities.

  有机催化的对映选择性Mannich反应，使用异氰基乙酸酯与异喹啉酮亚胺反应，并随后进行环化反应，产率高且立体选择性优异，形成螺环氧吲哚咪唑啉。
• Organocatalyzed asymmetric tandem conjugate addition–protonation of isocyanoacetates to 2-chloroacrylonitrile
  作者：Kun-Ming Yu、Hui-Kai Zhu、Xiao-Li Zhao、Min Shi、Mei-Xin Zhao

  DOI：10.1039/c8ob02833h

  日期：——

  organocatalytic asymmetric tandem conjugate addition–protonation of α-substituted isocyanoacetates to 2-chloroacrylonitrile catalyzed by dihydroquinine-derived thiourea has been investigated, affording the corresponding adducts with two non-adjacent tertiary–quaternary stereocenters in excellent yields (up to 99%) along with good to excellent diastereo- and enantioselectivities (up to 20 : 1 dr, up to 95%

  研究了一种有效的有机催化不对称串联共轭加成反应—由二氢奎宁衍生的硫脲催化α-取代的异氰基乙酸酯质子化成2-氯丙烯腈，并以优异的收率（高达99％）为相应的加合物提供了两个不相邻的叔-四级立体中心。在温和条件下具有良好至优异的非对映选择性和对映选择性（最高20：1 dr，最高95％ee）。该加合物还可以通过合成转化而转化为手性γ-内酰胺。
• <i>Cinchona</i> Alkaloid Squaramide-Catalyzed Asymmetric Ugi-Type Reaction of Isocyanoacetates with C,N-Cyclic Azomethine Imines: Access to Chiral Oxazole-Substituted Tetrahydroisoquinolines
  作者：Zi-Qiang Zhao、Xiao-Li Zhao、Min Shi、Mei-Xin Zhao

  DOI：10.1021/acs.joc.9b01955

  日期：2019.11.15

  We reported herein an unexpected cinchona alkaloid-derived squaramide-catalyzed asymmetric two-component Ugi-type reaction of α-aryl-substituted isocyanoacetates with C,N-cyclic azomethine imines, which provides concise access to optically active C1-oxazole-substituted tetrahydroisoquinolines in good yields (86-93%) and high enantioselectivities (up to 98% enantiomeric excess) under mild conditions

  我们在本文中报道了意料之外的金鸡纳生物碱衍生的方酰胺催化的α-芳基取代的异氰基乙酸酯与C，N-环偶氮甲亚胺的不对称两组分Ugi型反应，这提供了对光学活性C1-恶唑取代的四氢异喹啉的简明访问在温和条件下，收率高（86-93％），对映选择性高（对映体过量高达98％）。
• Temperature-Dependent <i>Cinchona</i> Alkaloid Squaramide-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Isocyanoacetates with β-Trifluoromethylated Enones
  作者：Mei-Xin Zhao、Guang-Yu Zhu、Hui-Kai Zhu、Xiao-Li Zhao、Ming Ji、Min Shi

  DOI：10.1002/ejoc.201800511

  日期：2018.8.7

  organocatalyzed asymmetric formal [3+2] cycloaddition reaction of isocyanoacetates to β‐trifluoromethylated enones is developed that directly affords chiral trifluoromethylated 2‐pyrrolines in good yield and high stereoselectivity.

  已开发出一种温度依赖性的异氰基乙酸酯与β-三氟甲基化烯酮的有机催化不对称甲醛[3 + 2]正式环加成反应，该反应可直接提供高收率和高立体选择性的手性三氟甲基化2-吡咯啉。