1-benzyl-3-(4-methylphenylsulfonyl)piperidine-2,6-dione | 330173-10-9

• 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-benzyl-3-(4-methylphenylsulfonyl)piperidine-2,6-dione
• 英文别名: 1-benzyl-3-(4-methylphenylsulfonyl)-2,6-azinanedione；2,6-Piperidinedione, 3-[(4-methylphenyl)sulfonyl]-1-(phenylmethyl)-；1-benzyl-3-(4-methylphenyl)sulfonylpiperidine-2,6-dione
• CAS: 330173-10-9
• 化学式: C₁₉H₁₉NO₄S
• 分子量: 357.43
• InChiKey: XQQRMGHJXULVDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1-benzyl-3-(4-methylphenylsulfonyl)piperidine-2,6-dione 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 1-Benzyl-6-hydroxy-5-(toluene-4-sulfonyl)-piperidin-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：

  1-benzyl-3-bromo-3-(4-methylphenylsulfonyl)piperidine-2,6-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以81%的产率得到1-benzyl-3-(4-methylphenylsulfonyl)piperidine-2,6-dione
  参考文献：
  名称：

  1,8-二氮杂双环[5.4.0]undec-7-ene：4-或5-取代的N-苄基α-溴-α-对甲苯磺酰戊二酰亚胺脱溴反应中的重要碱基

  摘要：

  b( ) a 生物化学研究所，中华民国台湾省南康市南康市中央研究院 b 国立中山大学化学系sity, Kaohsiung 804, Taiwan, ROC 用 1,8-二氮杂双环[5.4.0]undec-7-ene (DBU) 将 N-苄基 4-或 5-取代的-溴--对甲苯磺酰基戊二酰亚胺脱溴得到N-苄基4-或5-取代-对甲苯磺酰戊二酰亚胺。将 DBU/THF 系统应用于以中等收率合成双环戊二酰亚胺骨架的新方法。

  DOI：

  10.1002/jccs.200200145

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 N-alkyl-3-sulfonyl glutarimides to δ-lactams. Formal synthesis of (±)-paroxetine and (±)-tacamonine
  作者：Chung-Yi Chen、Bo-Rui Chang、Min-Ruei Tsai、Meng-Yang Chang、Nein-Chen Chang

  DOI：10.1016/j.tet.2003.09.076

  日期：2003.11

  A convenient method for the preparation of 4- or 5-substituted 3-sulfonyl-δ-lactams via regioselective reduction of N-alkyl-3-sulfonyl glutarimides is described. Formal synthesis of (±)-paroxetine and (±)-tacamonine is also reported.

  描述了一种通过区域选择性还原N-烷基-3-磺酰基戊二酰亚胺制备4-或5-取代的3-磺酰基-δ-内酰胺的简便方法。还报道了（±）-帕罗西汀和（±）-塔卡莫宁的形式合成。
• Reaction of different α-sulfonyl acetamides with methyl acrylate
  作者：Meng-Yang Chang、Shui-Tein Chen、Nein-Chen Chang

  DOI：10.1016/s0040-4020(02)00475-1

  日期：2002.6

  The base-induced tandem-coupling/cyclization reactions of various α-sulfonyl acetamide derivatives A with methyl acrylate differentiated between two different pathways to form α-sulfonyl analogs of glutarimides B and 2-hydroxycyclohexenecarboxylic acid derivatives C in different ratios. The reaction of α-sulfonyl acetamide dianion with methyl acrylate depended on three factors: the stability of the

  各种α-磺酰基乙酰胺衍生物A与丙烯酸甲酯的碱诱导的串联偶联/环化反应在两种不同的途径之间进行区分，从而以不同的比例形成戊二酰亚胺B和2-羟基环己烯羧酸衍生物C的α-磺酰基类似物。α-磺酰基乙酰胺二价阴离子与丙烯酸甲酯的反应取决于三个因素：二价阴离子的稳定性，丙烯酸甲酯的浓度以及磺酰和酰胺取代基的结构。通过改变反应条件，我们有效地控制了环加成反应以合成所需的产物，每种产物均具有潜在的生物学活性。提出了反应的闭环机理。
• One-pot facile conversion of Baylis–Hillman adduct into N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione. Formal synthesis of tacamonine
  作者：Chung-Yi Chen、Meng-Yang Chang、Ru-Ting Hsu、Shui-Tein Chen、Nein-Chen Chang

  DOI：10.1016/j.tetlet.2003.08.053

  日期：2003.11

  stepwise [3+3] strategy to N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione 1 used various N-alkyl α-substituted sulfonylacetamides 2 and α,β-unsaturated esters 3 as starting materials. α,β-Unsaturated esters 3 were generated by Baylis–Hillman reaction. A ring closure mechanism was proposed for the reactions. This method provides a convenient formal synthesis of tacamonine.

  N-烷基3-（E）-亚烷基-5-取代的磺酰基哌啶-2,6-二酮1的逐步[3 + 3]策略使用各种N-烷基α-取代的磺酰基乙酰胺2和α，β-不饱和酯3作为起始材料。α，β-不饱和酯3是通过Baylis-Hillman反应生成的。提出了反应的闭环机理。该方法提供了塔卡莫宁的方便的形式合成。
• Regioselective reduction of N-alkyl-3-sulfonyl glutarimides. Synthesis of 3,4-dihydro-3-tosylpyridin-2-ones
  作者：Bo-Rui Chang、Chung-Yi Chen、Nein-Chen Chang

  DOI：10.1016/s0040-4039(02)00446-x

  日期：2002.4

  Treatment of N-alkyl-3-sulfonyl glutarimides (1) with sodium hydride and then lithium aluminum hydride could give regioselective reduced hydroxy piperidones (5) which were further dehydrated to 3,4-dihydro-3-tosylpyridin-2-ones (6) in the presence of boron trifluoride.

  用氢化钠然后氢化铝锂处理N-烷基-3-磺酰基戊二酰亚胺（1），然后生成区域选择性的还原羟基哌啶酮（5），将其进一步脱水成3,4-二氢-3-甲苯磺酰基吡啶-2-酮（6））在三氟化硼的存在下。