1,3-dibenzyl-5-formyluracil | 57667-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-dibenzyl-5-formyluracil
• 英文别名: N,N'-dibenzyluracil-5-carbaldehyde；1,3-dibenzyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde；5-formyl-1,3-dibenzyluracil；1,3-Dibenzyl-2,4-dioxopyrimidine-5-carbaldehyde
• CAS: 57667-73-9
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: DAMLSYJBKFHJLH-UHFFFAOYSA-N

物化性质

• 沸点：
  505.0±60.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dibenzyl-5-formyluracil 在 4-甲基苯磺酸吡啶 原甲酸三乙酯 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 3-(1,3-dibenzyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,3-ethylenedioxypropionate
  参考文献：
  名称：

  A novel diketo phosphonic acid that exhibits specific, strand-transfer inhibition of HIV integrase and anti-HIV activity

  摘要：

  We have synthesized novel phosphonic acid analogues of P-diketo acids. Interestingly, the phosphonic acid isostere, 2, of our anti-HIV compound, 1, was an inhibitor of only the strand transfer step, in stark contrast to 1. Compound 2 had lower anti-HIV activity than 1, but was more active and less toxic than the phosphonic acid analogue of L-708906. These isosteric compounds represent the first examples of beta-diketo phosphonic acids of structural, synthetic, and antiviral interest. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.009
• 作为产物：
  描述：

  5-甲酰基尿嘧啶 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以89%的产率得到1,3-dibenzyl-5-formyluracil
  参考文献：
  名称：

  A novel diketo phosphonic acid that exhibits specific, strand-transfer inhibition of HIV integrase and anti-HIV activity

  摘要：

  We have synthesized novel phosphonic acid analogues of P-diketo acids. Interestingly, the phosphonic acid isostere, 2, of our anti-HIV compound, 1, was an inhibitor of only the strand transfer step, in stark contrast to 1. Compound 2 had lower anti-HIV activity than 1, but was more active and less toxic than the phosphonic acid analogue of L-708906. These isosteric compounds represent the first examples of beta-diketo phosphonic acids of structural, synthetic, and antiviral interest. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.009

文献信息

• Synthesis of Fluorine-Containing 3,3-Disubstituted Oxetanes and Alkylidene Oxetanes
  作者：Romain Laporte、Anais Prunier、Emmanuel Pfund、Vincent Roy、Luigi A. Agrofoglio、Thierry Lequeux

  DOI：10.1002/ejoc.201500172

  日期：2015.5

  contain a nucleic base, an ester or aryl sulfone function, and a pyrrolidine ring. Benzothiazolyl-sulfone-mediated aza-Michael addition reaction of nitrogen nucleophiles enables access to 3,3-disubstituted oxetanes.

  通过 Julia-Kocienski 反应从 3-氧杂环丁酮、3-氮杂环丁酮和氟砜实现了对氟亚烷基-氧杂环丁烷和 -氮杂环丁烷的访问。这种方法允许制备包含核碱基、酯或芳基砜功能和吡咯烷环的氟化四元环的新前体。苯并噻唑基砜介导的氮亲核试剂的氮杂-迈克尔加成反应能够获得 3,3-二取代氧杂环丁烷。
• WO2007/106450
  申请人：——

  公开号：——

  公开（公告）日：——
• A highly diastereoselective synthesis of homoallylic alcohol/amine appended uracils: the role of the uracil C-4 carbonyl in diastereoselectivity control
  作者：Subodh Kumar、Vijay Kumar、Satwinder Singh、Swapandeep Singh Chimni

  DOI：10.1016/s0040-4039(01)00797-3

  日期：2001.7

  5-Formyluracil derivatives and their Schiff bases with chiral amino alcohols undergo highly diastereoselective 1,2- and 1,3-allylations. The absence of the C-4 carbonyl in the case of 2,4-dimethoxy-5-formylpyrimidine and its Schiff bases leads to loss of diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Singh, Harjit; Singh, Palwinder; Chimni, Swapandeep Singh, Journal of the Chemical Society. Perkin transactions I, 1995, # 18, p. 2363 - 2368
  作者：Singh, Harjit、Singh, Palwinder、Chimni, Swapandeep Singh、Kumar, Subodh

  DOI：——

  日期：——
• THIELLIER H. P. M.; KOOMEN G.-J.; PANDIT U. K., HETEROCYCLES <HETC-A4>, 1975, 3, NO 9, 707-712
  作者：THIELLIER H. P. M.、 KOOMEN G.-J.、 PANDIT U. K.

  DOI：——

  日期：——