methyl 3-(phenylseleno)bicyclo<1.1.1>pentane-1-carboxylate | 156329-91-8

• 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: methyl 3-(phenylseleno)bicyclo<1.1.1>pentane-1-carboxylate
• 英文别名: Methyl 3-phenylselanylbicyclo[1.1.1]pentane-1-carboxylate
• CAS: 156329-91-8
• 化学式: C₁₃H₁₄O₂Se
• 分子量: 281.213
• InChiKey: YKTNSZWLGLOCJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(phenylseleno)bicyclo<1.1.1>pentane-1-carboxylate 在 sodium hydroxide 作用下， 反应 1.0h， 以96%的产率得到3-(phenylseleno)bicyclo<1.1.1>pentane-1-carboxylic acid
  参考文献：
  名称：

  Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclo[1.1.1]pentanes

  摘要：

  The synthesis of a wide variety of 1,3-disubstituted bicyclo[1.1.1]pentanes is described, with particular emphasis on the generation of a series of S-X-substituted bicyclo[1.1.1]pentyl bromides required for solvolytic studies. Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes in some instances, transformations were effected via carbanionic-type intermediates.

  DOI：

  10.1021/jo00090a015
• 作为产物：
  描述：

  二苯基二硒醚 、 2-thioxo-1,2-dihydropyridin-1-yl 3-(methoxycarbonyl)bicyclo<1.1.1>pentane-1-carboxylate 以 二氯甲烷 为溶剂， 反应 0.33h， 以77%的产率得到methyl 3-(phenylseleno)bicyclo<1.1.1>pentane-1-carboxylate
  参考文献：
  名称：

  Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclo[1.1.1]pentanes

  摘要：

  The synthesis of a wide variety of 1,3-disubstituted bicyclo[1.1.1]pentanes is described, with particular emphasis on the generation of a series of S-X-substituted bicyclo[1.1.1]pentyl bromides required for solvolytic studies. Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes in some instances, transformations were effected via carbanionic-type intermediates.

  DOI：

  10.1021/jo00090a015

文献信息

• Bio-inspired Halogen Bonding-Promoted Cross Coupling for the Synthesis of Organoselenium Compounds
  作者：Bo Li、Liang Yi、Bholanath Maity、Jiaqi Jia、Yuqin Shen、Xiang-Yu Chen、Luigi Cavallo、Magnus Rueping

  DOI：10.1021/acscatal.3c04601

  日期：2023.11.17

  vital in the fields of synthesis and catalysis. Herein, we describe the application of halogen bonding interactions to facilitate the reaction balance between an electron donor–acceptor (EDA) complex and Ph2Se2 for the synthesis of a series of organoselenium compounds. The EDA complex concept has recently emerged as an attractive path for visible light-induced transformations due to facile reaction

  非共价相互作用在许多有机和生化过程中发挥着重要作用，包括氢键和卤素键，它们在合成和催化领域至关重要。在此，我们描述了应用卤素键相互作用来促进电子供体-受体（EDA）络合物和Ph 2 Se 2之间的反应平衡，以合成一系列有机硒化合物。由于反应条件简单且无需使用光催化剂，EDA 复合物概念最近已成为可见光诱导转化的一条有吸引力的途径。密度泛函理论计算表明，碘-π*相互作用导致N- (酰氧基)邻苯二甲酰亚胺酯形成烷基自由基。生成的烷基被二硒化物-I•络合物捕获，形成C-Se 键。所开发的硒化物合成策略已应用于伯、仲、叔羧酸以及一系列天然产物、药物和α-硒氨基酸的转化。