(S)-3,3'-diethynyl-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-3,3'-diethynyl-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite
• 英文别名: 1-(10,16-Diethynyl-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-decaen-13-yl)pyrrolidine；1-(10,16-diethynyl-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-decaen-13-yl)pyrrolidine
• 化学式: C₂₈H₂₀NO₂P
• 分子量: 433.446
• InChiKey: KXOOLRKGCBMOKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-叠氮基-4-溴苯 、 (S)-3,3'-diethynyl-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 水 、 氯化铵 作用下， 以 乙腈 、 乙酸乙酯 为溶剂， 反应 15.0h， 以82%的产率得到3,3'-bis(1-(p-bromophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl N-(p-bromophenyl)(1-pyrrolidinyl)phosphonimidate
  参考文献：
  名称：

  Synthesis of modified binol-phosphoramidites

  摘要：

  A number of chiral phosphoramidite ligands containing electronically different N-heterocycles at the 3,3'-positions of the binol scaffold were synthesized. The nucleophilicity of the pendant heterocycles correlated with the propensity of the P(III) centre to undergo aerobic oxidation to P(V). Due to an unexpected Staudinger-type reaction between the product phosphoramidites, the order in which the individual synthetic transformations were conducted was found to be important. The synthesis of a phosphoramidite ligand containing flanking groups at the 3,3'-positions of the binol scaffold in addition to a stereogenic phosphorus atom was also undertaken. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.020
• 作为产物：
  描述：

  (S)-3,3'-diethynyl-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 在 盐酸 、 三氯化磷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 18.25h， 生成 (S)-3,3'-diethynyl-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite
  参考文献：
  名称：

  Synthesis of modified binol-phosphoramidites

  摘要：

  A number of chiral phosphoramidite ligands containing electronically different N-heterocycles at the 3,3'-positions of the binol scaffold were synthesized. The nucleophilicity of the pendant heterocycles correlated with the propensity of the P(III) centre to undergo aerobic oxidation to P(V). Due to an unexpected Staudinger-type reaction between the product phosphoramidites, the order in which the individual synthetic transformations were conducted was found to be important. The synthesis of a phosphoramidite ligand containing flanking groups at the 3,3'-positions of the binol scaffold in addition to a stereogenic phosphorus atom was also undertaken. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.020

文献信息

• Towards the synthesis of N-heterocycle containing BINOL-phosphoramidites
  作者：Carl Recsei、Christopher S.P. McErlean

  DOI：10.1016/j.tetasy.2009.12.019

  日期：2010.2

  The first synthesis of a 3,3'-bis-N-heterocycle BINOL-based chiral phosphoramidite ligand is described. The synthesis of a 3,3'-dipyridyl-BINOL-phosphoramidite was prohibited by rapid oxidation at phosphorus. The 3,3'-bistriazolyl-BINOL compound was synthesised using an azide-alkyne cycloaddition, in which the choice of solvent and amine base proved critical. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of modified binol-phosphoramidites
  作者：Carl Recsei、Christopher S.P. McErlean

  DOI：10.1016/j.tet.2011.11.020

  日期：2012.1

  A number of chiral phosphoramidite ligands containing electronically different N-heterocycles at the 3,3'-positions of the binol scaffold were synthesized. The nucleophilicity of the pendant heterocycles correlated with the propensity of the P(III) centre to undergo aerobic oxidation to P(V). Due to an unexpected Staudinger-type reaction between the product phosphoramidites, the order in which the individual synthetic transformations were conducted was found to be important. The synthesis of a phosphoramidite ligand containing flanking groups at the 3,3'-positions of the binol scaffold in addition to a stereogenic phosphorus atom was also undertaken. (C) 2011 Elsevier Ltd. All rights reserved.