2'-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)-[1,1'-binaphthalen]-2-yl 4-methylbenzenesulfonate | 1356476-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2'-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)-[1,1'-binaphthalen]-2-yl 4-methylbenzenesulfonate
• CAS: 1356476-35-1
• 化学式: C₄₇H₃₁O₆PS
• 分子量: 754.799
• InChiKey: BVPCNGIBRJNVIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.49
• 重原子数：
  55.0
• 可旋转键数：
  6.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.02
• 拓扑面积：
  78.88
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (S)-2'-hydroxy-1,1'-binaphthyl-2-yl 4-toluenesulfonate 、 (R)-(1,1′-联萘-2,2′-二氧)氯膦 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以74%的产率得到2'-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)-[1,1'-binaphthalen]-2-yl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Phosphites and diamidophosphites based on mono-ethers of BINOL: a comparison of enantioselectivity in asymmetric catalytic reactions

  摘要：

  Novel P-monodentate phosphite-type ligands have been synthesized in one step from BINOL monotosylate and BINOL mono-(-)-menthylcarbonate. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylic substitution of (E)-1,3-diphenylallyl acetate and up to 99% ee in Rh-catalyzed asymmetric addition of phenylboronic acid to cyclohex-2-enone. The influence of the structural modules such as the nature of phosphorus-containing ring or exocyclic substituent on the enantioselectivity is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.092
• 作为试剂：
  描述：

  2-环己烯-1-酮 、 苯硼酸 在 chlorobis(ethylene)rhodium(I) dimer 、 2'-(dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yloxy)-[1,1'-binaphthalen]-2-yl 4-methylbenzenesulfonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 72.0h， 生成 (R)-3-苯基环己酮 、 (S)-3-苯基环己酮
  参考文献：
  名称：

  Phosphites and diamidophosphites based on mono-ethers of BINOL: a comparison of enantioselectivity in asymmetric catalytic reactions

  摘要：

  Novel P-monodentate phosphite-type ligands have been synthesized in one step from BINOL monotosylate and BINOL mono-(-)-menthylcarbonate. The use of these ligands provides up to 96% ee in Pd-catalyzed asymmetric allylic substitution of (E)-1,3-diphenylallyl acetate and up to 99% ee in Rh-catalyzed asymmetric addition of phenylboronic acid to cyclohex-2-enone. The influence of the structural modules such as the nature of phosphorus-containing ring or exocyclic substituent on the enantioselectivity is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.092