anti-4-phenyl-1-tosyl-6-vinyltetrahydropyrimidin-2(1H)-one

• 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: anti-4-phenyl-1-tosyl-6-vinyltetrahydropyrimidin-2(1H)-one
• 英文别名: (4S,6S)-6-ethenyl-1-(4-methylphenyl)sulfonyl-4-phenyl-1,3-diazinan-2-one
• 化学式: C₁₉H₂₀N₂O₃S
• 分子量: 356.445
• InChiKey: WXGDVPYJDUVUGG-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  anti-4-phenyl-1-tosyl-6-vinyltetrahydropyrimidin-2(1H)-one 在 盐酸 、 甲醇 、 magnesium 作用下， 以 水 为溶剂， 反应 19.0h， 生成 syn-1-phenylpent-4-ene-1,3-diamine dihydrochloride
  参考文献：
  名称：

  Tosylureas 的立体发散钯和铑催化分子内加成到阿连烯：四氢嘧啶酮的非对映选择性合成

  摘要：

  当采用基于钯或铑的催化体系时，甲苯磺酰脲与丙二烯的分子内加成具有高度的顺/反非对映选择性，并提供 1,3-环脲。在钯催化下，一系列热力学反-四氢嘧啶酮是可用的，而铑催化允许合成动力学顺-四氢嘧啶酮。对于具有代表性的底物范围，两种环状脲均以优异的产率和非对映选择性获得。获得的四氢嘧啶酮显示出易于脱保护和修饰以证明合成价值。

  DOI：

  10.1021/acs.orglett.1c03482
• 作为产物：
  描述：

  1-苯基-4-戊烯-1-酮 在 正丁基锂 、 Pd(TFA)2/bis-sulfoxide 、 ammonium acetate 、 sodium cyanoborohydride 、 苯基-P-苯醌 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 anti-4-phenyl-1-tosyl-6-vinyltetrahydropyrimidin-2(1H)-one
  参考文献：
  名称：

  Pd(II)-Catalyzed Allylic C–H Amination for the Preparation of 1,2- and 1,3-Cyclic Ureas

  摘要：

  A general synthesis of 1,2- and 1,3-cyclic ureas is accomplished by intramolecular allylic C-H amination employing Pd(TFA)(2)/bis-sulfoxide as a catalyst. By careful modification of substrates and catalyst, a variety of 1,2-cyclic ureas are accessible from not previously employed terminal olefins substituted in allylic or vinylic positions. Furthermore, MS4A is found to be an effective additive for the synthesis of 1,3-cyclic ureas in good yields and excellent diastereoselectivities.

  DOI：

  10.1021/ol5037453

文献信息

• Stereodivergent Synthesis of 1,3-<i>syn</i>- and -<i>anti</i>-Tetrahydropyrimidinones
  作者：Michael Morgen、Sebastian Bretzke、Pengfei Li、Dirk Menche

  DOI：10.1021/ol101755m

  日期：2010.10.15

  An efficient protocol for the stereoselective synthesis of 1,3-syn and -anti-tetrahydropyrimidinones (syn- and anti-11a) is reported The modular procedure is based on a stereodivergent cyclization of readily available urea-type substrates (10a) by intramolecular allylic substitution The cyclization proceeds with excellent yield (up to 99%) and selectivity (up to dr > 20:1), purely based on substrate control The product pyrimidines can be readily transformed into the corresponding free syn- and anti-amines
• Pd(II)-Catalyzed Allylic C–H Amination for the Preparation of 1,2- and 1,3-Cyclic Ureas
  作者：Yasuhiro Nishikawa、Seikou Kimura、Yuri Kato、Natsuka Yamazaki、Osamu Hara

  DOI：10.1021/ol5037453

  日期：2015.2.20

  A general synthesis of 1,2- and 1,3-cyclic ureas is accomplished by intramolecular allylic C-H amination employing Pd(TFA)(2)/bis-sulfoxide as a catalyst. By careful modification of substrates and catalyst, a variety of 1,2-cyclic ureas are accessible from not previously employed terminal olefins substituted in allylic or vinylic positions. Furthermore, MS4A is found to be an effective additive for the synthesis of 1,3-cyclic ureas in good yields and excellent diastereoselectivities.
• Stereodivergent Palladium- and Rhodium-Catalyzed Intramolecular Addition of Tosylureas to Allenes: Diastereoselective Synthesis of Tetrahydropyrimidinones
  作者：Arne G. A. Geissler、Jasmin R. Riesterer、Bernhard Breit

  DOI：10.1021/acs.orglett.1c03482

  日期：2021.12.3

  palladium or rhodium-based catalytic system and affords 1,3-cyclic ureas. Under palladium catalysis a range of thermodynamic anti-tetrahydropyrimidinones are accessible, while rhodium catalysis allows synthesis of the kinetic syn-tetrahydropyrimidinones. For a representative scope of substrates both cyclic ureas were obtained in excellent yields and diastereoselectivities. The obtained tetrahydropyrimidinones

  当采用基于钯或铑的催化体系时，甲苯磺酰脲与丙二烯的分子内加成具有高度的顺/反非对映选择性，并提供 1,3-环脲。在钯催化下，一系列热力学反-四氢嘧啶酮是可用的，而铑催化允许合成动力学顺-四氢嘧啶酮。对于具有代表性的底物范围，两种环状脲均以优异的产率和非对映选择性获得。获得的四氢嘧啶酮显示出易于脱保护和修饰以证明合成价值。