(6S)-1,4-Diacetyl-6-methyl-3-methylidenepiperazine-2,5-dione | 169612-51-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6S)-1,4-Diacetyl-6-methyl-3-methylidenepiperazine-2,5-dione
• 英文别名: (3S)-1,4-diacetyl-3-methyl-6-methylidenepiperazine-2,5-dione
• CAS: 169612-51-5
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: HFJRVZQATWGDMD-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6S)-1,4-Diacetyl-6-methyl-3-methylidenepiperazine-2,5-dione 在 一水合肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 184.0h， 生成 8-methyl-3-(2,4,6-trimethylphenyl)-1-oxa-2,6,9-triazaspiro[4.5]dec-2-ene-7,10-dione
  参考文献：
  名称：

  Directed 1,3-dipolar cycloadditions of ylidene piperazine-2,5-diones

  摘要：

  The reactivities and selectivities of 1,3-dipolar cycloaddition reactions of ylidene piperazine-2,5-diones with mesitonitrile oxide are reported. The stereoselectivities of reactions with chiral ylidene piperazine-2,5-diones can be directed by judicious choice of substituents on the N- and/or C-substituents of the piperazinedione ring. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.040
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-L-alanyl-L-serine methyl ester 在 palladium on activated charcoal 咪唑 、 氢气 、 三氯化铁 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (6S)-1,4-Diacetyl-6-methyl-3-methylidenepiperazine-2,5-dione
  参考文献：
  名称：

  Stereocontrolled intermolecular radical additions to methylidenepiperazine-2,5-diones

  摘要：

  报道了利用潜在的氨基酸功能团合成亚甲基哌嗪-2,5-二酮的方法。这些哌嗪二酮是合成功能化哌嗪二酮和氨基酸的潜在手性模板。通过亚甲基哌嗪二酮与一系列烷基自由基之间的自由基加成反应形成碳-碳键，获得了良好的收率。观察到了中等至高的非对映选择性，并在此讨论了控制手性诱导的因素。

  DOI：

  10.1039/a900771g

文献信息

• Guidelines for stereocontrolled Diels–Alder reactions of chiral methylidene piperazine-2,5-diones with cyclopentadiene
  作者：Brendan A Burkett、Christina L.L Chai

  DOI：10.1016/s0040-4039(01)00151-4

  日期：2001.3

  The reactivities and stereoselectivities of Diels–Alder cycloaddition reactions of methylidene piperazine-2,5-diones with cyclopentadiene can be manipulated by appropriate choice of N- and α-carbon substituents. Good to excellent exo/endo and facial selectivities were obtained.

  的亚甲基哌嗪-2,5-二酮与环戊二烯的狄尔斯-阿尔德环加成反应的反应性和立体选择性可以通过适当地选择被操纵Ñ和α碳的取代基- 。获得了良好至优异的外切/内切和面部选择性。
• Methylene piperazine-2,5-diones as templates for the synthesis of amino acid derivatives
  作者：Christina L.L. Chai、Alison R. King

  DOI：10.1016/0040-4039(95)00743-v

  日期：1995.6

  Methylene piperazine-2,5-diones 5a and 5b are important synthetic intermediates. The preparation as well as the use of these compounds in the synthesis of amino acid derivatives are described. Our studies demonstrate that excellent chiral induction in carbon-carbon bond forming reactions can be obtained with methylene piperazinedione 5b.
• Stereocontrolled intermolecular radical additions to methylidenepiperazine-2,5-diones
  作者：Christina L. L. Chai、Alison R. King

  DOI：10.1039/a900771g

  日期：——

  The use of latent amino acid functionalities for the syntheses of methylidenepiperazine-2,5-diones is reported. These piperazinediones are potential chiral templates in the synthesis of functionalised piperazinediones and amino acids. Carbon–carbon bond formation utilising radical addition reactions between the methylidenepiperazinediones and a number of alkyl radicals resulted in good yields of the addition adduct. Moderate to high diastereoselectivities were observed and factors controlling the chiral induction are discussed here.

  报道了利用潜在的氨基酸功能团合成亚甲基哌嗪-2,5-二酮的方法。这些哌嗪二酮是合成功能化哌嗪二酮和氨基酸的潜在手性模板。通过亚甲基哌嗪二酮与一系列烷基自由基之间的自由基加成反应形成碳-碳键，获得了良好的收率。观察到了中等至高的非对映选择性，并在此讨论了控制手性诱导的因素。
• Directed 1,3-dipolar cycloadditions of ylidene piperazine-2,5-diones
  作者：Christina L.L Chai、Alison J Edwards、Bronwyn A Wilkes、Ruth C.J Woodgate

  DOI：10.1016/j.tet.2003.09.040

  日期：2003.10

  The reactivities and selectivities of 1,3-dipolar cycloaddition reactions of ylidene piperazine-2,5-diones with mesitonitrile oxide are reported. The stereoselectivities of reactions with chiral ylidene piperazine-2,5-diones can be directed by judicious choice of substituents on the N- and/or C-substituents of the piperazinedione ring. (C) 2003 Elsevier Ltd. All rights reserved.