(S)-1,1'-binaphthalene-2,2'-diylbis(3,1-phenylene) dimethylphosphoramidite | 1187984-70-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1,1'-binaphthalene-2,2'-diylbis(3,1-phenylene) dimethylphosphoramidite
• 英文别名: N,N-dimethyl-27,29-dioxa-28-phosphaheptacyclo[28.3.1.122,26.02,11.05,10.012,21.013,18]pentatriaconta-1(34),2(11),3,5,7,9,12(21),13,15,17,19,22(35),23,25,30,32-hexadecaen-28-amine
• CAS: 1187984-70-8
• 化学式: C₃₄H₂₆NO₂P
• 分子量: 511.56
• InChiKey: OCZFRDQPIFVBMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  38
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吗啉 、 (S)-1,1'-binaphthalene-2,2'-diylbis(3,1-phenylene) dimethylphosphoramidite 在 5-苯基四氮唑 作用下， 以 甲苯 为溶剂， 以25%的产率得到(S)-1,1'-binaphthalene-2,2'-diylbis(3,1-phenylene) morpholin-1-ylphosphonite
  参考文献：
  名称：

  Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis

  摘要：

  Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)-C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.041
• 作为产物：
  描述：

  (S)-3,3'-(1,1'-binaphthalene-2,2'-diyl)bisphenol 、 三(二甲胺基)膦 在 氯化铵 作用下， 以 苯 为溶剂， 反应 4.0h， 以37%的产率得到(S)-1,1'-binaphthalene-2,2'-diylbis(3,1-phenylene) dimethylphosphoramidite
  参考文献：
  名称：

  Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis

  摘要：

  Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)-C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.041
• 作为试剂：
  描述：

  4-氯苯亚甲基丙酮 、 diethylzinc 在 (S)-1,1'-binaphthalene-2,2'-diylbis(3,1-phenylene) dimethylphosphoramidite 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 (+/-)-4-(4-chlorophenyl)-hexan-2-one 、 (+/-)-4-(4-chlorophenyl)-hexan-2-one
  参考文献：
  名称：

  Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis

  摘要：

  Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)-C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.041

文献信息

• Bisphenylene homologues of BINOL-based phosphoramidites: synthesis, stereostructure, and application in catalysis
  作者：Natalia Miklášová、Ondřej Julínek、Michaela Mešková、Vladimír Setnička、Marie Urbanová、Martin Putala

  DOI：10.1016/j.tetlet.2010.02.041

  日期：2010.4

  Bis-ortho- and bis-meta-phenylene homologues of BINOL-based N,N-dimethylphosphoramidites were prepared from the corresponding diols by treatment with hexamethyltriaminophosphane. Phosphoramidites derived from bulkier secondary amines were synthesized by 5-phenyl-1H-tetrazole-promoted amine exchange. All the phosphoramidites were obtained as single diastereomers. Their configurations at the C(naphthyl)-C(phenyl) axes were determined by vibrational circular dichroism (VCD) spectroscopy. Preliminary testing of the ligands in copper-catalyzed conjugate addition of diethylzinc to acyclic enones and nitrostyrene gave the corresponding products in up to 74% ee. (C) 2010 Elsevier Ltd. All rights reserved.