(3R*,4S*)-1-benzyl-4-methyl-3-(toluene-4-sulfonyl)-3,4-dihydro-5H-pyridine-2,6-dione

• 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: (3R*,4S*)-1-benzyl-4-methyl-3-(toluene-4-sulfonyl)-3,4-dihydro-5H-pyridine-2,6-dione
• 英文别名: (3R,4S)-1-benzyl-4-methyl-3-(4-methylphenyl)sulfonylpiperidine-2,6-dione
• 化学式: C₂₀H₂₁NO₄S
• 分子量: 371.457
• InChiKey: ATYPRKHHCNTZAS-HNAYVOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R*,4S*)-1-benzyl-4-methyl-3-(toluene-4-sulfonyl)-3,4-dihydro-5H-pyridine-2,6-dione 在 sodium tetrahydroborate 、 三氯化铝 、 三氟化硼乙醚 、 magnesium sulfate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 20.5h， 生成 1-(3-chloropropyl)-4-methyl-5-(toluene-4-sulfonyl)-3,4-dihydropyridin-2-one
  参考文献：
  名称：

  Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of the Indolizidine 8a-epi-Dendroprimine

  摘要：

  Sodium borohydride regioselectively reduced various 3-sulfonyl glutarimides 1 to hydroxy piperidones 2, which were further dehydrated to 3,4-dihydro-5-sulfonylpyridin-2-ones 3 in the presence of boron trifluoride. Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5.

  DOI：

  10.1021/jo025539p
• 作为产物：
  描述：

  N-苄基-2-氯乙酰胺 在 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 (3R*,4S*)-1-benzyl-4-methyl-3-(toluene-4-sulfonyl)-3,4-dihydro-5H-pyridine-2,6-dione
  参考文献：
  名称：

  Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of the Indolizidine 8a-epi-Dendroprimine

  摘要：

  Sodium borohydride regioselectively reduced various 3-sulfonyl glutarimides 1 to hydroxy piperidones 2, which were further dehydrated to 3,4-dihydro-5-sulfonylpyridin-2-ones 3 in the presence of boron trifluoride. Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5.

  DOI：

  10.1021/jo025539p

文献信息

• An efficient synthesis of N-benzyl-3-sulfonyl glutarimides. Formal synthesis of the aromatase inhibitor AG-1
  作者：Meng-Yang Chang、Bo-Rui Chang、Huo-Mu Tai、Nein-Chen Chang

  DOI：10.1016/s0040-4039(00)01845-1

  日期：2000.12

  A formal [3+3] cycloaddition strategy to substituted glutarimides was studied. N-Benzyl α-sulfonylacetamides and various α,β-unsaturated esters were used as starting materials.

  研究了取代的戊二酰亚胺的正式的[3 + 3]环加成策略。使用N-苄基α-磺酰基乙酰胺和各种α，β-不饱和酯作为起始原料。
• Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of the Indolizidine 8a-<i>e</i><i>pi</i>-Dendroprimine
  作者：Ru-Ting Hsu、Li-Ming Cheng、Nein-Chen Chang、Huo-Mu Tai

  DOI：10.1021/jo025539p

  日期：2002.7.1

  Sodium borohydride regioselectively reduced various 3-sulfonyl glutarimides 1 to hydroxy piperidones 2, which were further dehydrated to 3,4-dihydro-5-sulfonylpyridin-2-ones 3 in the presence of boron trifluoride. Formal synthesis of 8a-epi-dendroprimine (4) possessing an indolizidine ring system has been accomplished via intramolecular radical cyclization of cyclic vinyl sulfone 5.