3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate | 1352523-02-4

• 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)phosphonate
• 英文别名: 4-[13-Oxido-13-pyrrolidin-1-yl-16-[1-(2,4,5-trichlorophenyl)triazol-4-yl]-12,14-dioxa-13-phosphoniapentacyclo[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-oxido-13-pyrrolidin-1-yl-16-[1-(2,4,5-trichlorophenyl)triazol-4-yl]-12,14-dioxa-13-phosphoniapentacyclo[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: 1352523-02-4
• 化学式: C₄₀H₂₄Cl₆N₇O₃P
• 分子量: 894.367
• InChiKey: WWCKCYWFQRRCND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  57
• 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：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-1,1'-binaphthyl-2,2'-diyl (1-pyrrolidinyl)phosphonate 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 以99%的产率得到3,3'-bis(1-(2,4,5-trichlorophenyl)-1H-1,2,3-triazol-4-yl)-2,2'-dihydroxy-1,1'-binaphthyl
  参考文献：
  名称：

  Accessing Brominated Natural Product Motifs Using Phosphoramidite Catalysis

  摘要：

  本文介绍了第一代磷酰胺催化剂在构建最常见的含溴天然产物亚基中的应用。文章将该工艺与之前的工作进行了比较，发现其与现有方法具有互补性。应用该工艺可以使用实验室常用试剂 N-溴代琥珀酰亚胺进行溴代碳环化、溴化乙醚化和溴代烯的形成。

  DOI：

  10.1071/ch14539
• 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

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.
• Accessing Brominated Natural Product Motifs Using Phosphoramidite Catalysis
  作者：Carl Recsei、Christopher S. P. McErlean

  DOI：10.1071/ch14539

  日期：——

  This article describes the application of a first-generation phosphoramidite catalyst to the construction of the most commonly encountered subunits of bromine-containing natural products. The process is compared with previous efforts, and is found to be complementary to existing methods. Application of the process enables bromocarbocyclisations, bromoetherifications, and bromoallene formation using the common laboratory reagent N-bromosuccinimide.

  本文介绍了第一代磷酰胺催化剂在构建最常见的含溴天然产物亚基中的应用。文章将该工艺与之前的工作进行了比较，发现其与现有方法具有互补性。应用该工艺可以使用实验室常用试剂 N-溴代琥珀酰亚胺进行溴代碳环化、溴化乙醚化和溴代烯的形成。