4-烯丙基-2,6-哌啶二酮 | 918868-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-烯丙基-2,6-哌啶二酮
• 英文名称: 3-allylglutarimide
• 英文别名: 4-prop-2-enylpiperidine-2,6-dione
• CAS: 918868-36-7
• 化学式: C₈H₁₁NO₂
• mdl: MFCD11226883
• 分子量: 153.181
• InChiKey: NBLMGXRDBAQIBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-烯丙基-2,6-哌啶二酮 在 Hoveyda-Grubbs catalyst second generation 、 palladium on activated charcoal 吡啶 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 135.0h， 生成 hepta-2,6-dienoic acid 5-(tert-butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxy)-1-[5-(2,6-dioxo-piperidin-4-yl)-1-methyl-2-oxo-pentyl]-6-methoxy-2,4-dimethyl-hept-2-enyl ester
  参考文献：
  名称：

  Synthesis of migrastatin and its macrolide core

  摘要：

  Migrastatin and its macrolactone subunit are potent antimetastatic agents. Both were synthesized by using a ring-closing metathesis (RCM) to establish the macrolactone core, and the control of the (Z)-trisubstituted double bond at C11-C12 was achieved by using a Still-Gennari olefination. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.107
• 作为产物：
  描述：

  3-(2-propenyl)-glutaric acid 在 尿素 作用下， 反应 2.67h， 以87%的产率得到4-烯丙基-2,6-哌啶二酮
  参考文献：
  名称：

  Synthesis of migrastatin and its macrolide core

  摘要：

  Migrastatin and its macrolactone subunit are potent antimetastatic agents. Both were synthesized by using a ring-closing metathesis (RCM) to establish the macrolactone core, and the control of the (Z)-trisubstituted double bond at C11-C12 was achieved by using a Still-Gennari olefination. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.107

文献信息

• 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。
• Synthesis of migrastatin and its macrolide core
  作者：Sébastien Reymond、Janine Cossy

  DOI：10.1016/j.tet.2007.02.107

  日期：2007.6

  Migrastatin and its macrolactone subunit are potent antimetastatic agents. Both were synthesized by using a ring-closing metathesis (RCM) to establish the macrolactone core, and the control of the (Z)-trisubstituted double bond at C11-C12 was achieved by using a Still-Gennari olefination. (C) 2007 Elsevier Ltd. All rights reserved.