naplephos-h | 1225431-75-3

• 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: naplephos-h
• 英文别名: [(2R,4aR,6S,7R,8R,8aS)-7-[(2-diphenylphosphanylbenzoyl)amino]-2-(4-methoxyphenyl)-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2-phenylacetate
• CAS: 1225431-75-3
• 化学式: C₄₈H₄₄NO₈P
• 分子量: 793.853
• InChiKey: XRYWKUQEWOZFPC-LRQPVBKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  58
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  naplephos-h 在 水 、 三乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 naplephos-h'
  参考文献：
  名称：

  New tagged naplephos ligands for asymmetric allylic substitutions under traditional and unconventional conditions

  摘要：

  This paper demonstrates the versatility of the class of chiral ligands naplephos, which has been further refined by preparing new 'tagged' versions for selective use in polar media (e.g., ionic liquids). These modified types, along with the best performing original varieties, have been examined in two Pd-catalysed asymmetric processes involving C-C and C-N bond formation. High ees have been achieved in traditional solvents, while the experiments performed in ionic liquids confirm the difficulty of predicting the outcome of a reaction in these media and the general decrease in the catalytic performance. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.013
• 作为产物：
  描述：

  苯乙酸 、 N-[(2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-(4-methoxyphenyl)-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-diphenylphosphanylbenzamide 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 naplephos-h
  参考文献：
  名称：

  Naplephos: a modular library of chiral phosphines based on d-glucose for highly enantioselective asymmetric catalysis

  摘要：

  Simple functionalisation of N-acetylglucosamine produces the modular ligand library naplephos, which combines the performance of 'privileged' ligands based on 1,2-trans-cyclohexanediamine with flexibility and accessibility. With the proper choice of substituents, the basic structure was suitably adapted to the Pd-catalysed asymmetric allylic alkylation of rac-(E)-1,3-dipheny1-2-propenyl acetate with dimethyl malonate, producing the (S)-product in ee's of up to 96% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.005

文献信息

• Naplephos: a modular library of chiral phosphines based on d-glucose for highly enantioselective asymmetric catalysis
  作者：Vincenzo Benessere、Francesco Ruffo

  DOI：10.1016/j.tetasy.2010.01.005

  日期：2010.2

  Simple functionalisation of N-acetylglucosamine produces the modular ligand library naplephos, which combines the performance of 'privileged' ligands based on 1,2-trans-cyclohexanediamine with flexibility and accessibility. With the proper choice of substituents, the basic structure was suitably adapted to the Pd-catalysed asymmetric allylic alkylation of rac-(E)-1,3-dipheny1-2-propenyl acetate with dimethyl malonate, producing the (S)-product in ee's of up to 96% ee. (C) 2010 Elsevier Ltd. All rights reserved.
• New tagged naplephos ligands for asymmetric allylic substitutions under traditional and unconventional conditions
  作者：Vincenzo Benessere、Matteo Lega、Alba Silipo、Francesco Ruffo

  DOI：10.1016/j.tet.2011.05.013

  日期：2011.7

  This paper demonstrates the versatility of the class of chiral ligands naplephos, which has been further refined by preparing new 'tagged' versions for selective use in polar media (e.g., ionic liquids). These modified types, along with the best performing original varieties, have been examined in two Pd-catalysed asymmetric processes involving C-C and C-N bond formation. High ees have been achieved in traditional solvents, while the experiments performed in ionic liquids confirm the difficulty of predicting the outcome of a reaction in these media and the general decrease in the catalytic performance. (C) 2011 Elsevier Ltd. All rights reserved.