2-(2,5-difluorophenyl)-1,3,2-dioxaborolane | 1338601-20-9

• 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: 2-(2,5-difluorophenyl)-1,3,2-dioxaborolane
• CAS: 1338601-20-9
• 化学式: C₈H₇BF₂O₂
• 分子量: 183.95
• InChiKey: XYBWYVFXGPGPIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,5-difluorophenyl)-1,3,2-dioxaborolane 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine 、 sodium acetate 、 caesium carbonate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 31.0h， 生成 (1R,2S)-2-(2,5-difluorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes

  摘要：

  An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intra-molecular Friedel Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.

  DOI：

  10.1021/jo201781x
• 作为产物：
  描述：

  乙二醇 、 2,5-二氟苯硼酸 以 甲苯 为溶剂， 反应 24.0h， 以100%的产率得到2-(2,5-difluorophenyl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes

  摘要：

  An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intra-molecular Friedel Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.

  DOI：

  10.1021/jo201781x

文献信息

• Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes
  作者：Jennifer Tsoung、Katja Krämer、Adam Zajdlik、Clemence Liébert、Mark Lautens

  DOI：10.1021/jo201781x

  日期：2011.11.4

  An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intra-molecular Friedel Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.