3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite | 1352523-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite
• 英文别名: 4-[13-Pyrrolidin-1-yl-16-[1-(2,4,5-trichlorophenyl)triazol-4-yl]-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-10-yl]-1-(2,4,5-trichlorophenyl)triazole；4-[13-pyrrolidin-1-yl-16-[1-(2,4,5-trichlorophenyl)triazol-4-yl]-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-10-yl]-1-(2,4,5-trichlorophenyl)triazole
• CAS: 1352523-00-2
• 化学式: C₄₀H₂₄Cl₆N₇O₂P
• 分子量: 878.368
• InChiKey: BBRRGBROSYISPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  56
• 可旋转键数：
  5
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 在 盐酸 、 甲醇 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氯化磷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 、 1,3-二氯苯 为溶剂， 反应 41.0h， 生成 3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 、 3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate
  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
• 作为试剂：
  描述：

  3-furanyl geranyl ketone 在 [RhCl2(p-cymene)]2 、 3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonite 、 sodium formate 、 十六烷基三甲基溴化铵 、 (1S,2S)-(+)-N-对甲苯磺酰基-1,2-二苯基乙二胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 23.25h， 生成 (4S,6R,7R,10R)-2-(furan-3-yl)-7,11,11-trimethyloctahydrobenzofuran
  参考文献：
  名称：

  Synthesis of (+)-Luzofuran and (−)-Ancistrofuran

  摘要：

  The first synthesis of the furan-containing snyderane, (+)-luzofuran, is reported. The key step in this approach was an electrophilic brominative cyclization, which was accomplished using a nucleophilic N-heterocycle-flanked phosphoramidite catalyst in combination with the common laboratory reagent N-bromosuccinimide.

  DOI：

  10.1021/jo402790x

文献信息

• 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.