2-dodecyl di-o-nitrobenzyl phosphate | 1133062-79-9

• 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: 2-dodecyl di-o-nitrobenzyl phosphate
• 英文别名: 2-dodecyldi-o-nitrobenzylphosphate；1-[[Dodecan-2-yloxy-[(2-nitrophenyl)methoxy]-oxidophosphaniumyl]oxymethyl]-2-nitrobenzene；1-[[dodecan-2-yloxy-[(2-nitrophenyl)methoxy]-oxidophosphaniumyl]oxymethyl]-2-nitrobenzene
• CAS: 1133062-79-9
• 化学式: C₂₆H₃₇N₂O₈P
• 分子量: 536.562
• InChiKey: DMHOGBISCJNSCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-十二烷醇 、 bis-(2-nitrobenzyl)-N,N-diisopropylphosphoramidite 在 四氮唑 、 异氰酸苯酯 、 双氧水 作用下， 以 二氯甲烷 、 乙腈 、 水 为溶剂， 反应 17.0h， 以23%的产率得到2-dodecyl di-o-nitrobenzyl phosphate
  参考文献：
  名称：

  Efficient catalyst turnover in the phosphitylation of alcohols with phosphoramidites

  摘要：

  We report a method for catalytic phosphitylation utilizing phosphoramidites. Traditionally, this reaction is inefficient unless an excess of catalyst is present due to catalyst deactivation by an amine by-product. Isocyanate additives have been evaluated for scavenging the amine to facilitate catalyst turnover. A variety of alcohols and phosphoramidites were screened with 5 mol % catalyst. In the presence of additive, 83-97% conversion was achieved in contrast to 7-31% conversion without additive. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.065

文献信息

• Catalytic Lewis acid phosphorylation with pyrophosphates
  作者：Owen S. Fenton、Emily E. Allen、Kyle P. Pedretty、Sean D. Till、Joseph E. Todaro、Bianca R. Sculimbrene

  DOI：10.1016/j.tet.2012.08.070

  日期：2012.11

  We report a method for the Lewis acid catalyzed phosphorylation of alcohols with pyrophosphates. Ti((OBu)-Bu-t)(4) was found to be the most effective catalyst in the phosphorylation of both primary and secondary alcohols with tetrabenzylpyrophosphate, providing conversions between 54% and >98% and isolated yields between 50% and 97%. Other pyrophosphates with orthogonal protecting groups were synthesized and screened to validate the generality of the approach. This study will describe how benzyl, methyl, ethyl, allyl, and o-nitrobenzyl pyrophosphates are all effective phosphorylating agents under Lewis acid catalysis. (C) 2012 Elsevier Ltd. All rights reserved.
• Efficient catalyst turnover in the phosphitylation of alcohols with phosphoramidites
  作者：Patrick B. Brady、Elizabeth M. Morris、Owen S. Fenton、Bianca R. Sculimbrene

  DOI：10.1016/j.tetlet.2008.12.065

  日期：2009.3

  We report a method for catalytic phosphitylation utilizing phosphoramidites. Traditionally, this reaction is inefficient unless an excess of catalyst is present due to catalyst deactivation by an amine by-product. Isocyanate additives have been evaluated for scavenging the amine to facilitate catalyst turnover. A variety of alcohols and phosphoramidites were screened with 5 mol % catalyst. In the presence of additive, 83-97% conversion was achieved in contrast to 7-31% conversion without additive. (C) 2008 Elsevier Ltd. All rights reserved.