4-(2-ethoxyethyl)benzonitrile

• 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: 4-(2-ethoxyethyl)benzonitrile
• 英文别名: 4-(2-Ethoxyethyl)benzonitrile
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: ZKWSJBOPMZLUJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯苯甲腈 、 乙烯基乙醚 在 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 sodium formate 、 mesna 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 16.0h， 以81%的产率得到4-(2-ethoxyethyl)benzonitrile
  参考文献：
  名称：

  通过二氧化碳自由基阴离子 (CO2•–) 进行自由基链还原

  摘要：

  我们开发了一种有效的还原自由基形成方法，该方法利用二氧化碳的自由基阴离子 (CO 2 •– ) 作为强大的单电子还原剂。通过亲电自由基和甲酸盐之间的极性匹配氢原子转移 (HAT)，CO 2 •–形成作为新的自由基链式反应的关键元素。在这里，自由基链引发可以通过光化学或热方式进行，我们说明了这种方法实现一系列底物类别的还原活化的能力。具体来说，我们将这种策略用于未活化烯烃与（杂）芳基氯化物/溴化物的分子间加氢芳基化、芳基铵盐的自由基脱氨基、脂肪族酮基自由基的形成和磺酰胺裂解。我们表明，CO 2 •–与贫电子烯烃的反应性导致单电子还原或烯烃加氢羧化，其中底物还原电位可用于预测反应结果。

  DOI：

  10.1021/jacs.1c04427

文献信息

• 1,2,4-oxadiazole derivatives and their therapeutic use
  申请人：Laboratorios Almirall, S.A.

  公开号：EP2202232A1

  公开（公告）日：2010-06-30

  New derivatives of general formula (I), or pharmaceutically acceptable salts or N-oxides thereof wherein, A is selected from the group consisting of -N-, -O- and -S-; B and C are independently selected from the group consisting of-N- and -O-, with the proviso that at least two of A, B and C are nitrogen atoms; G1 is selected from the group consisting of -CH2-, -NH- and -O-; G2 is selected from the group consisting of -NR4- and -O-; R1 represents: ➢ a 8 to 10 membered bicyclic N-containing heteroaryl group optionally substituted with a C1-4 carboxyalkyl group or a C1-4 aminoalkyl group, ➢ a pyridyl group optionally substituted with one or more substituents selected from hydroxy groups, C1-4 alkyl groups, C1-4 carboxyalkyl groups, C1-4 haloalkyl groups, C1-4 alkoxy groups, amino groups, C1-4 aminoalkyl groups and C1-4 aminoalkoxy groups, ➢ a pyridone group substituted with one or more C1-4 alkyl groups; C1-4 haloalkyl groups or C1-4 aminoalkyl groups, or ➢ a group of formula: wherein: • Ra represents a hydrogen atom, a halogen atom, a C1-4 alkyl group, C3-4 cycloalkyl group or a -CF3 group; • Rb represents a hydrogen atom, a halogen atom, a C14 alkyl group, a -CF3 group or a C1-4 alkoxy group; • Rd represents a hydrogen atom, a C1-4 alkyl group or a C1-4 alkoxy group; • Rc represents: ○ a hydrogen atom, a C1-4 hydroxyalkyl group, a C1-4 aminoalkyl group which is optionally substituted with one or more substituents selected from halogen atoms, hydroxy groups and -CF3 groups; ○ a 4 to 6-membered saturated N-containing heterocyclic ring optionally substituted with a C1-2 carboxyalkyl group; ○ -(CH2)(0-4)-C(O)OR', -(CH2)(0-4)-C(O)NR'R", -(CH2)(0-4)-NHC(O)R", -S(O)2NR'R", -O-(CH2)(2-4)NR'R", -O-(CH2)(1-4)C(O)OR", -O-(CH2)(1-4)-C(O)NR'R", -(CH2)(0-4)-NR'R", -(CH2)(0-4)-CONHS(O)2R', -(CH2)(0-4)-NHS(O)2R' or -(CH2)(0-3)-N H-(CH2)(1-3)-(NH)(0-1)S(O)2R' wherein, ■ R' represents a hydrogen atom or a C1-4 alkyl group, ■ R" represents a hydrogen atom, a C1-4 alkyl group, a C3-4 cycloalkyl group, a C1-4 carboxyalkyl group, a C1-4 haloalkyl group, a C1-4 hydroxyalkyl group or a 6 membered, saturated N-containing heterocyclic ring, or ■ R' and R" together with the nitrogen atom to which they are attached from a 4 to 6 membered heterocyclic group which contains, as heteroatoms, one N atom and, optionally, one further atom selected from N and O, and which is optionally substituted with a carboxy or a C1-4 carboxyalkyl group, or Rc together with Rd form a C5-6 cycloalkyl group optionally substituted by a -NHRf group, wherein Rf is selected from the group consisting of a hydrogen atom and a carboxymethyl group; R2 and R3 are independently selected from the group consisting of hydrogen atoms, halogen atoms and C1-4 alkyl groups; and R4 is selected from the group consisting of a hydrogen atom, a phenyl group, a C3-4 cycloalkyl-C1-4 alkyl group, C1-4 aminoalkyl group, C1-4 haloalkyl group and a linear or branched C1-4 alkyl group which is optionally substituted by a phenyl or a pyridyl group.

  通用公式（I）的新衍生物，或其药用可接受盐或N-氧化物，其中， A选自-N-，-O-和-S-组成的群; B和C分别选自-N-和-O-组成的群，但至少有两个A，B和C是氮原子; G1选自-CH2-，-NH-和-O-组成的群; G2选自-NR4-和-O-组成的群; R1代表: ➢一个含氮杂环的8到10成员双环基团，可选择地取代为C1-4羧基烷基基团或C1-4氨基烷基基团， ➢一个吡啶基，可选择地取代为一个或多个取代基，所选取代基包括羟基、C1-4烷基基团、C1-4羧基烷基基团、C1-4卤代烷基基团、C1-4烷氧基团、氨基、C1-4氨基烷基基团和C1-4氨氧基团， ➢一个吡啶酮基，取代为一个或多个C1-4烷基基团；C1-4卤代烷基基团或C1-4氨基烷基基团，或 ➢一个公式的基团： 其中: • Ra代表氢原子、卤原子、C1-4烷基基团、C3-4环烷基基团或-CF3基团; • Rb代表氢原子、卤原子、C14烷基基团、-CF3基团或C1-4烷氧基团; • Rd代表氢原子、C1-4烷基基团或C1-4烷氧基团; • Rc代表: ○氢原子、C1-4羟基烷基基团、C1-4氨基烷基基团，可选择地取代为一个或多个取代基，所选取代基包括卤原子、羟基和-CF3基团; ○一个4到6成员饱和的含氮杂环环，可选择地取代为C1-2羧基烷基基团; ○-(CH2)(0-4)-C(O)OR'，-(CH2)(0-4)-C(O)NR'R"，-(CH2)(0-4)-NHC(O)R"，-S(O)2NR'R"，-O-(CH2)(2-4)NR'R"，-O-(CH2)(1-4)C(O)OR"，-O-(CH2)(1-4)-C(O)NR'R"，-(CH2)(0-4)-NR'R"，-(CH2)(0-4)-CONHS(O)2R'，-(CH2)(0-4)-NHS(O)2R'或-(CH2)(0-3)-N H-(CH2)(1-3)-(NH)(0-1)S(O)2R'其中， ■ R'代表氢原子或C1-4烷基基团， ■ R"代表氢原子、C1-4烷基基团、C3-4环烷基基团、C1-4羧基烷基基团、C1-4卤代烷基基团、C1-4羟基烷基基团或6成员饱和的含氮杂环环，或 ■ R'和R"与它们连接的氮原子一起形成一个4到6成员的杂环基团，该基团包含一个N原子和可选择地一个进一步选择自N和O的原子，并可选择地取代为羧基或C1-4羧基烷基基团， 或Rc与Rd一起形成一个可选择地由-NHRf基团取代的C5-6环烷基基团，其中Rf选自氢原子和羧甲基基团; R2和R3分别选自氢原子、卤原子和C1-4烷基基团;和 R4选自氢原子、苯基团、C3-4环烷基-C1-4烷基基团、C1-4氨基烷基基团、C1-4卤代烷基基团和可选择地由苯基或吡啶基取代的线性或支链C1-4烷基基团。
• Radical Chain Reduction via Carbon Dioxide Radical Anion (CO₂^•–)
  作者：Cecilia M. Hendy、Gavin C. Smith、Zihao Xu、Tianquan Lian、Nathan T. Jui

  DOI：10.1021/jacs.1c04427

  日期：2021.6.23

  developed an effective method for reductive radical formation that utilizes the radical anion of carbon dioxide (CO2•–) as a powerful single electron reductant. Through a polarity matched hydrogen atom transfer (HAT) between an electrophilic radical and a formate salt, CO2•– formation occurs as a key element in a new radical chain reaction. Here, radical chain initiation can be performed through photochemical

  我们开发了一种有效的还原自由基形成方法，该方法利用二氧化碳的自由基阴离子 (CO 2 •– ) 作为强大的单电子还原剂。通过亲电自由基和甲酸盐之间的极性匹配氢原子转移 (HAT)，CO 2 •–形成作为新的自由基链式反应的关键元素。在这里，自由基链引发可以通过光化学或热方式进行，我们说明了这种方法实现一系列底物类别的还原活化的能力。具体来说，我们将这种策略用于未活化烯烃与（杂）芳基氯化物/溴化物的分子间加氢芳基化、芳基铵盐的自由基脱氨基、脂肪族酮基自由基的形成和磺酰胺裂解。我们表明，CO 2 •–与贫电子烯烃的反应性导致单电子还原或烯烃加氢羧化，其中底物还原电位可用于预测反应结果。