(R)-F13BINAPO

• 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: (R)-F13BINAPO
• 英文别名: [6-Diphenylphosphoryl-5-[2-diphenylphosphoryl-6-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]naphthalen-1-yl]naphthalen-2-yl]-tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane；[6-diphenylphosphoryl-5-[2-diphenylphosphoryl-6-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]naphthalen-1-yl]naphthalen-2-yl]-tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane
• 化学式: C₉₂H₅₄F₇₈O₂P₂Si₂
• 分子量: 2791.43
• InChiKey: AFBUYKWADKDLCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  37.02
• 重原子数：
  176
• 可旋转键数：
  51
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  80

反应信息

• 作为反应物：
  描述：

  (R)-F13BINAPO 在 三氟甲烷磺酸甲酯 、 lithium aluminium tetrahydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 以68%的产率得到(R)-F13BINAP
  参考文献：
  名称：

  Preparation of a fluorous chiral BINAP and application to an asymmetric Heck reaction

  摘要：

  Fluorous chiral BINAP ((R)-F(13)BINAP) was prepared and,as applied to an asymmetric Heck reaction. The enantioselectivity as similar in BTF homogeneous system (90% ee) to that of the original non-fluorous reaction and marginally higher in benzene and FC-72 biphasic system (93% ee) than that of the original non-fluorous one. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00407-0
• 作为产物：
  描述：

  二苯基膦 、 [1-[2-(Trifluoromethylsulfonyloxy)-6-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]naphthalen-1-yl]-6-[tris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silyl]naphthalen-2-yl] trifluoromethanesulfonate 在 1,2-双(二苯基膦)乙烷氯化镍 双氧水 作用下， 以 various solvent(s) 为溶剂， 反应 72.0h， 以87%的产率得到(R)-F13BINAPO
  参考文献：
  名称：

  Preparation of a fluorous chiral BINAP and application to an asymmetric Heck reaction

  摘要：

  Fluorous chiral BINAP ((R)-F(13)BINAP) was prepared and,as applied to an asymmetric Heck reaction. The enantioselectivity as similar in BTF homogeneous system (90% ee) to that of the original non-fluorous reaction and marginally higher in benzene and FC-72 biphasic system (93% ee) than that of the original non-fluorous one. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00407-0

文献信息

• Enantioselective carbon–carbon bond forming reactions using fluorous chiral catalysts
  作者：Yutaka Nakamura、Seiji Takeuchi、Yoshiaki Ohgo

  DOI：10.1016/s0022-1139(02)00320-2

  日期：2003.4

  Fluorous chiral BINOLs and BINAP were prepared and used as the ligands for an asymmetric addition of Et2Zn to aromatic aldehydes and an asymmetric Heck reaction, respectively. The enantioselectivities were similar in homogeneous system to those of the original non-fluorous reactions. Consecutive reactions were examined by utilizing fluorous-organic biphase and fluorous solid phase extraction techniques. Enantioselectivities in consecutive reactions were close to that attained in the non-fluorous system. The solid phase extraction method also enabled us to perform a simultaneous screening procedure. (C) 2002 Elsevier Science B.V. All rights reserved.