(2R,3R)-2,3-bis(4-fluorophenyl)oxirane | 212058-54-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2R,3R)-2,3-bis(4-fluorophenyl)oxirane
• CAS: 212058-54-3
• 化学式: C₁₄H₁₀F₂O
• 分子量: 232.23
• InChiKey: OWHJBDCDCALEQQ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-bis(4-fluorophenyl)oxirane 在 copper nanoparticles on black carbon 、 (二甲基苯硅烷基)硼酸频那醇酯 、 lithium hexamethyldisilazane 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以87%的产率得到(Z)-1,2-bis(4-fluorophenyl)ethene
  参考文献：
  名称：

  Copper Nanocrystal Plane Effect on Stereoselectivity of Catalytic Deoxygenation of Aromatic Epoxides

  摘要：

  Previous studies have shown that crystal planes of heterogeneous catalysts could display enhanced activity, such that higher turnover or chemoselectivity could be achieved. Here we report an example where the reaction stereoselectivity was significantly affected by the catalyst crystal planes. In copper-catalyzed deoxygenation reaction of aromatic epoxides, copper cubes, wires, and plates gave the olefin products with different cis/trans selectivities, whereas homogeneous copper catalysts showed poor selectivity. Scanning tunneling microscope and density functional theory studies revealed that the different adsorption mode and higher adsorption strength of epoxide oxygen on Cu{100} plane were responsible for the observed variation of selectivity. The copper-catalyzed deoxygenation reaction provided new practical access to cis-olefins from readily available aromatic epoxides. Our work also indicated that nanocrystal catalysts may provide useful stereochemical control in organic reactions.

  DOI：

  10.1021/jacs.5b01391
• 作为产物：
  描述：

  (E)-1,2-di(4-fluorophenyl)ethene 在 三甲基氯硅烷 、 甲基磺酰胺 、 potassium carbonate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 44.0h， 生成 (2R,3R)-2,3-bis(4-fluorophenyl)oxirane
  参考文献：
  名称：

  C 2对称双（氮丙啶）配体在某些过渡金属介导的不对称转化中的比较研究

  摘要：

  已对各种取代的C 2对称双（氮丙啶）配体在各种金属介导的不对称反应中的性能进行了比较研究。所研究的金属是（二羟基化），钯（烯丙基烷基化）和铜（环丙烷化和叠氮化），选择的配体可以评估电子和空间效应。对于钯的配合物，电子效应最为明显，钯的配合物似乎很松散地结合到这种配体上。对于其他金属，空间效应起着更重要的作用。图选项

  DOI：

  10.1016/s0040-4020(98)00987-9

文献信息

• 10.1002/ejoc.202400613
  作者：Kawamoto, Yuki、Yoshimura, Tomoyuki、Matsuo, Jun-ichi

  DOI：10.1002/ejoc.202400613

  日期：——

  Unusual C−C bond cleavage of 2,3-diaryl aziridines took place to afford secondary amines by formal dihydrogenation and hydrocyanation. Formal dehydrogenation was performed by electrocyclic ring opening of N-Li or N-Na aziridines to azaallyl anions followed by reduction with NaBH4. Formal hydrocyanation was realized by treating azaallyl anions with Me3SiCN.

  2,3-二芳基氮丙啶的不寻常 C-C 键裂解通过正式的二氢化和氢氰化得到仲胺。通过将 N-Li 或 N-Na 氮杂环啶电循环开环化为氮杂烯丙基阴离子，然后用 NaBH4 还原来进行正式脱氢。通过用 Me3SiCN 处理氮杂烯丙基阴离子实现正式氢氰化。
• Copper Nanocrystal Plane Effect on Stereoselectivity of Catalytic Deoxygenation of Aromatic Epoxides
  作者：Bin Xiao、Zhiqiang Niu、Yang-Gang Wang、Wei Jia、Jian Shang、Lan Zhang、Dingsheng Wang、Yao Fu、Jie Zeng、Wei He、Kai Wu、Jun Li、Jinlong Yang、Lei Liu、Yadong Li

  DOI：10.1021/jacs.5b01391

  日期：2015.3.25

  Previous studies have shown that crystal planes of heterogeneous catalysts could display enhanced activity, such that higher turnover or chemoselectivity could be achieved. Here we report an example where the reaction stereoselectivity was significantly affected by the catalyst crystal planes. In copper-catalyzed deoxygenation reaction of aromatic epoxides, copper cubes, wires, and plates gave the olefin products with different cis/trans selectivities, whereas homogeneous copper catalysts showed poor selectivity. Scanning tunneling microscope and density functional theory studies revealed that the different adsorption mode and higher adsorption strength of epoxide oxygen on Cu100} plane were responsible for the observed variation of selectivity. The copper-catalyzed deoxygenation reaction provided new practical access to cis-olefins from readily available aromatic epoxides. Our work also indicated that nanocrystal catalysts may provide useful stereochemical control in organic reactions.
• A comparative study of C2-symmetric bis(aziridine) ligands in some transition metal-mediated asymmetric transformations
  作者：David Tanner、Fredrik Johansson、Adrian Harden、Pher G. Andersson

  DOI：10.1016/s0040-4020(98)00987-9

  日期：1998.12

  A comparative study has been made of the performance of differently substituted C2-symmetric bis(aziridine) ligands in a variety of metal-mediated asymmetric reactions. The metals studied were osmium (dihydroxylation), palladium (allylic alkylation) and copper (cyclopropanation and aziridination), the ligands being chosen so as to allow evaluation of both electronic and steric effects. The electronic

  已对各种取代的C 2对称双（氮丙啶）配体在各种金属介导的不对称反应中的性能进行了比较研究。所研究的金属是（二羟基化），钯（烯丙基烷基化）和铜（环丙烷化和叠氮化），选择的配体可以评估电子和空间效应。对于钯的配合物，电子效应最为明显，钯的配合物似乎很松散地结合到这种配体上。对于其他金属，空间效应起着更重要的作用。图选项