1-(phenylmethyl)-4-phenylpiperidin-2,6-dione | 62143-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(phenylmethyl)-4-phenylpiperidin-2,6-dione
• 英文别名: 1-benzyl-4-phenyl-piperidine-2,6-dione；1-Benzyl-4-phenyl-piperidin-2,6-dion；1-Benzyl-4-phenylpiperidine-2,6-dione
• CAS: 62143-51-5
• 化学式: C₁₈H₁₇NO₂
• mdl: MFCD09221421
• 分子量: 279.338
• InChiKey: QOUSZMRKBNBUCP-UHFFFAOYSA-N

物化性质

• 沸点：
  497.7±44.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(phenylmethyl)-4-phenylpiperidin-2,6-dione 在 硼烷四氢呋喃络合物 、 B-methyl-(1S)-amino-(2S)-indanol 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from cis-1-Amino-indan-2-ol

  摘要：

  Enantioselective reductive desymmetrization of glutarimides,has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process, that upgraded the enantioselectivity of an intermediate,hydroxy-lactam. The reaction: was generally tolerant of a number of substituents in the 4-position giving enantiomeric excesses of greater than 82%.

  DOI：

  10.1021/acs.joc.5b02177
• 作为产物：
  描述：

  2-phenyl-1,1,3,3-tetraethoxycarbonylpropane 在 1,4-二氧六环 、 氢溴酸 作用下， 250.0 ℃ 、14.71 MPa 条件下， 生成 1-(phenylmethyl)-4-phenylpiperidin-2,6-dione
  参考文献：
  名称：

  Paden; Adkins, Journal of the American Chemical Society, 1936, vol. 58, p. 2493

  摘要：

  DOI：

文献信息

• Chemoselective Hydrogenation of Imides Catalyzed by Cp*Ru(PN) Complexes and Its Application to the Asymmetric Synthesis of Paroxetine
  作者：Masato Ito、Ayaka Sakaguchi、Chika Kobayashi、Takao Ikariya

  DOI：10.1021/ja067777y

  日期：2007.1.1

  This work represents the first catalytic hydrogenation of imides into amides and primary alcohols, in which the unique chemoselectivity is originated from the bifunctional nature of ruthenium-NH moiety in the catalyst.

  这项工作代表了第一次将酰亚胺催化氢化成酰胺和伯醇，其中独特的化学选择性源于催化剂中钌-NH 部分的双功能性质。
• Catalytic Enantioselective Desymmetrization of Prochiral Triacylamines via Pseudopeptidic Guanidine–Guanidinium Catalysis
  作者：Hu Qu、Xin-Shen Liang、Wen-Juan Wang、Xian-He Zhao、Yu-Hua Deng、Xian-Tao An、Wen-Dao Chu、Xiang-Zhi Zhang、Chun-An Fan

  DOI：10.1021/acs.orglett.2c02785

  日期：2022.9.23

  Triacylamines with Cs symmetry have been explored in asymmetric organocatalysis, leading to the development of a novel catalytic enantioselective desymmetrization of prochiral triacylamines by methanolysis under the catalysis of chiral pseudopeptidic guanidine–guanidinium salt having a weakly coordinating anion. This organocatalytic methodology provides an effective approach to the synthetically useful

  已经在不对称有机催化中探索了具有C s对称性的三酰基胺，从而在具有弱配位阴离子的手性假肽胍-胍盐的催化下通过甲醇分解开发了一种新的催化对映选择性去对称化前手性三酰基胺。这种有机催化方法为合成有用的具有 1,5-二羰基部分的手性酰亚胺酯提供了一种有效的方法，其合成潜力已在两种 GABA 类似药物的不对称合成中得到体现，( R )-巴氯芬·HCl 和 ( S )-普瑞巴林。
• Mallard; Wilson, Journal of the American Pharmaceutical Association (1912), 1957, vol. 46, p. 176
  作者：Mallard、Wilson

  DOI：——

  日期：——
• Paden; Adkins, Journal of the American Chemical Society, 1936, vol. 58, p. 2493
  作者：Paden、Adkins

  DOI：——

  日期：——
• Enantioselective Desymmetrization of Glutarimides Catalyzed by Oxazaborolidines Derived from <i>cis</i>-1-Amino-indan-2-ol
  作者：Ibrahim U. Kutama、Simon Jones

  DOI：10.1021/acs.joc.5b02177

  日期：2015.11.20

  Enantioselective reductive desymmetrization of glutarimides,has been achieved employing an oxazaborolidine catalyst derived from cis-1-amino-indan-2-ol. The reaction was found to proceed through a stereoablative process, that upgraded the enantioselectivity of an intermediate,hydroxy-lactam. The reaction: was generally tolerant of a number of substituents in the 4-position giving enantiomeric excesses of greater than 82%.