2-(4-phenylbutyl) dibenzyl phosphate | 1133062-84-6

• 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-(4-phenylbutyl) dibenzyl phosphate
• 英文别名: 2-(4-phenylbutyl)dibenzyl phosphate；3-[Oxido-bis(phenylmethoxy)phosphaniumyl]oxybutylbenzene；3-[oxido-bis(phenylmethoxy)phosphaniumyl]oxybutylbenzene
• CAS: 1133062-84-6
• 化学式: C₂₄H₂₇O₄P
• 分子量: 410.45
• InChiKey: SHJGYSQJLAEAAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苯基-2-丁醇 、 焦磷酸四苄酯 在 titanium(IV) tetrabutoxide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以80%的产率得到2-(4-phenylbutyl) dibenzyl phosphate
  参考文献：
  名称：

  Catalytic Lewis acid phosphorylation with pyrophosphates

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.08.070

文献信息

• 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.