1,3-dibenzyldihydropyrimidine-2,4(1H,3H)-dione | 75500-04-8

• 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-dibenzyldihydropyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-dibenzylhexahydropyrimidine-2,4-dione；N1,N3-dibenzyl-5,6-dihydrouracil；5,6-dihydro-1,3-dibenzyluracil；1,3-dibenzyl-dihydrouracil；1,3-dibenzyldihydrouracyl；1,3-Dibenzyl-1,3-diazinane-2,4-dione
• CAS: 75500-04-8
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: NIOJPZBGMXIOOV-UHFFFAOYSA-N

物化性质

• 沸点：
  458.2±48.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-dibenzyldihydropyrimidine-2,4(1H,3H)-dione 在 potassium tert-butylate 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 氘代二甲亚砜 、 二氯甲烷 、 水 为溶剂， 反应 14.25h， 生成 (E)-1,3-dibenzyl-5-(fluoromethylene)dihydropyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  A Unified Strategy for the Synthesis of Difluoromethyl- and Vinylfluoride-Containing Scaffolds

  摘要：

  Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.

  DOI：

  10.1021/acs.orglett.9b02887
• 作为产物：
  描述：

  溴甲苯 在 水 、 L-Selectride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.08h， 生成 1,3-dibenzyldihydropyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  以三仲丁基硼氢化锂为还原剂的正嵌段二氢尿嘧啶和二氢乳清酸衍生物的新合成

  摘要：

  用三仲丁基硼氢化锂将1，3-二-N-取代的尿嘧啶及其衍生物还原成相应的5，6-二氢化合物，产率极高。尿嘧啶5-位的烷基化也很方便地完成。

  DOI：

  10.1016/s0040-4039(01)83925-3

文献信息

• Ammonium Formate/Palladium on Carbon: A Versatile System for Catalytic Hydrogen Transfer Reductions of Carbon-Carbon Double Bonds
  作者：Zdzisław Paryzek、Hanna Koenig、Bartłomiej Tabaczka

  DOI：10.1055/s-2003-41024

  日期：——

  Various carbon-carbon double bonds in olefins and α,β-unsaturated ketones were effectively reduced to the corresponding alkanes and saturated ketones, using ammonium formate as a hydrogen transfer agent in the presence ofPd/C as catalyst in refluxing methanol.

  以甲酸铵为氢转移剂，Pd/C为催化剂，甲醇回流。
• Iridium‐Catalyzed β‐C(sp ² )−H Borylation of Enamides – Access to 3,3‐Dihalogeno‐2‐methoxypiperidines
  作者：Isabelle Gillaizeau、Ismaël Dondasse、Cyril Nicolas、Liliane Mimoun、Volodymyr Sukach、Hervé Meudal

  DOI：10.1002/ejoc.202101302

  日期：2022.1.17

  An efficient iridium-catalyzed C(sp2)−H reaction of non-aromatic tertiary enamides was successfully developed under mild reaction conditions and with high regioselectivity, leading to original C-3 borylated enamides in good yields. These derivatives could then be exploited in Suzuki cross-coupling reactions, or converted into valuable 3,3-dihalogenopiperidine derivatives through short reaction times

  在温和的反应条件和高区域选择性下，成功地开发了一种有效的铱催化的非芳族叔烯酰胺的C( sp 2 )-H 反应，从而以良好的收率得到原始的 C-3 硼化烯酰胺。这些衍生物随后可用于 Suzuki 交叉偶联反应，或通过短反应时间以中等至良好的产率转化为有价值的 3,3-二卤代哌啶衍生物。
• THE PREPARATION OF 1-ALLYLURACIL. <i>N</i>(1)-ALKYLATION OF <i>N</i>(3)-PROTECTED URACIL DERIVATIVES
  作者：Zdzislaw Paryzek、Bartlorniej Tabaczka

  DOI：10.1080/00304940109356610

  日期：2001.8

  (2001). THE PREPARATION OF 1-ALLYLURACIL. N(1)-ALKYLATION OF N(3)-PROTECTED URACIL DERIVATIVES. Organic Preparations and Procedures International: Vol. 33, No. 4, pp. 400-405.

  (2001)。1-烯丙基脲的制备。N(3)-保护的尿嘧啶衍生物的N(1)-烷基化。国际有机制剂和程序：卷。33，第 4 期，第 400-405 页。
• 5-Trihydroxypropyl-dihydrouracil derivatives as precursors of 1-azasugars: application to the stereoselective synthesis of d-galacto-isofagomine
  作者：Pietro Spanu、Cristina de Candia、Fausta Ulgheri

  DOI：10.1016/j.tetlet.2010.02.093

  日期：2010.5

  A new route for the synthesis of isofagomine analogues has been carried out by using as precursors enantiopure 5-trihydroxypropyl-dihydrouracil derivatives obtained from aldol-type addition of 1,3-dibenzyl-dihydrouracil to isopropylidene-protected glyceraldehyde. The synthesis of d-galacto-isofagomine is reported.

  通过使用对映体纯的5-三羟丙基-二氢尿嘧啶衍生物作为前体，进行了异黄花碱类似物的合成新路线，该对映体是从1，3-二苄基-二氢尿嘧啶的醛醇型加成到异亚丙基保护的甘油醛而获得的。报道了d-半乳糖-异黄酮的合成。
• Use of 1,3-dibenzyl-dihydrouracil in the chain extension of 2,3-O-isopropylidene-d-glyceraldehyde
  作者：Fausta Ulgheri、John Bacsa、Luigi Nassimbeni、Pietro Spanu

  DOI：10.1016/s0040-4039(02)02701-6

  日期：2003.1

  The aldol-type addition of 1,3-dibenzyl-dihydrouracil 2 to 2,3-O-isopropylidene-d-glyceraldehyde 3 was examined in different solvents and under Lewis acid catalysis in order to establish the stereochemical preferences. A stereodivergent synthesis of 5-trihydroxypropyl-dihydrouracil derivatives 4 and its C-5 epimer 5 was realized. The synthesis of ureido polyols 8 and 10 was obtained via the reductive

  为了确定立体化学偏好，在不同的溶剂中和在路易斯酸催化下检查了将1，3-二苄基-二氢尿嘧啶2醛醇型加成到2，3 - O-异亚丙基-d-甘油醛3中。实现了5-三羟丙基-二氢尿嘧啶衍生物4及其C-5差向异构体5的立体发散合成。通过模板4和5的还原性开环获得脲基多元醇8和10的合成。