(S)-2-(hexafluoroisopropyloxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine | 379268-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2-(hexafluoroisopropyloxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine
• 英文别名: 13-(1,1,1,3,3,3-Hexafluoropropan-2-yloxy)-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene
• CAS: 379268-55-0
• 化学式: C₂₃H₁₃F₆O₃P
• 分子量: 482.319
• InChiKey: CAAMIXHNUAKCOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  di(rhodium)tetracarbonyl dichloride 、 (S)-2-(hexafluoroisopropyloxy)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 以 not given 为溶剂， 生成
  参考文献：
  名称：

  Enantioselective Pd-catalysed allylation with BINOL-derived monodentate phosphite and phosphoramidite ligands

  摘要：

  P-monodentate phosphite (1) and phosphoramidite (2) ligands have been synthesised from (S)-BINOL. Complexation of the new ligands with [Rh(CO)(2)Cl](2) and [Pd(allyl)Cl](2) has been found to give neutral and cationic complexes [Rh(CO)Cl(L)](2) and [Pd(allyl)(L)(2)]+BF4-, correspondingly. Applicability of these ligands in asymmetric C*-C, C*-N, C*-S bond formation and alkene hydrogenation reactions has been demonstrated. The phosphoramidite 2 showed higher enantioselectivity than its phosphite analogue I and provided good enantio selectivity in the Pd-catalysed allylic substitution of 1,3-diphenylallyl acetate with dimethyl malonate (up to 90% ee), sodium para-toluene sulfinate (up to 75% ee), pyrrolidine (up to 65% ee) and sodium diformylamide (up to 68% ee), as well as in the Rh-catalysed hydrogenation of dimethyl itaconate (up to 76% ee). (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2005.01.023

文献信息

• Asymmetric Pd-catalyzed allylic amination of 1,3-diphenylallyl acetate with dipropylamine in ionic and molecular solvents
  作者：S. E. Lyubimov、V. A. Davankov、A. S. Kucherenko、S. G. Zlotin、S. V. Zheglov、K. N. Gavrilov、P. V. Petrovskii

  DOI：10.1007/s11172-006-0155-9

  日期：2005.11

  Asymmetric catalytic allylic amination of 1,3-diphenylallyl acetate with dipropylamine in an ionic liquid, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, and in THF and CH2Cl2 in the presence of palladium complexes of P-monodentate phosphite and phosphoramidite derivatives of S-1,1′-bis-2-naphthol was carried out. This gave a product with ee of up to 65%. The level of asymmetric induction is retained after three catalyst cycles.

  在离子液体 1-丁基-2,3-二甲基咪唑鎓四氟硼酸盐中，以及在 THF 和 CH2Cl2 中，在 S-1,1′-双-2-萘酚的亚磷酸 P-monodentate 和亚磷酰胺衍生物的钯络合物存在下，进行了 1,3-二苯基烯丙基乙酸酯与二丙胺的不对称催化烯丙基胺化反应。这样得到的产品ee高达 65%。经过三次催化剂循环后，不对称诱导水平得以保持。