N-benzenesulfonyl-2-piperidone | 7744-25-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzenesulfonyl-2-piperidone
• 英文别名: 1-(phenylsulfonyl)-piperidin-2-one；1-(Benzenesulfonyl)piperidin-2-one
• CAS: 7744-25-4
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: PFNXLCWXLXMZLL-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±25.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzenesulfonyl-2-piperidone 在 三乙基硅烷 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.17h， 生成 1-(苯磺酰基)哌啶
  参考文献：
  名称：

  An efficient protocol for the selective reduction of benzenesulfonyllactam to benzenesulfonyl cyclic amine

  摘要：

  The selective reduction of N-benzenesulfonylpiperidin-2-one to N-benzenesulfonylpiperidine was accomplished through the use of NaBH4 with either ZrCl4 or SnCl4 and by silane-mediated two-step reductions. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00696-5
• 作为产物：
  描述：

  哌啶酮 在 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N-benzenesulfonyl-2-piperidone
  参考文献：
  名称：

  Sheu, Jennline; Smith, Michael B.; Oeschger, Thomas R., Organic Preparations and Procedures International, 1992, vol. 24, # 2, p. 147 - 158

  摘要：

  DOI：

文献信息

• Reactivity and stereoselectivity of the Diels–Alder reaction using cyclic dienophiles and siloxyaminobutadienes
  作者：Toshiyuki Ohfusa、Atsushi Nishida

  DOI：10.1016/j.tet.2011.01.019

  日期：2011.3

  Several bicyclic compounds were synthesized by the Diels–Alder reaction using aminodiene and a cyclic dienophile. The stereochemistries of the obtained adducts were determined by X-ray crystallography or NMR analysis. The stereoselectivity of this Diels–Alder reaction was based on the interaction of molecular orbitals between the diene and dienophile. The reactivities of these Diels–Alder reactions

  使用氨基二烯和环状亲二烯体通过Diels-Alder反应合成了几种双环化合物。通过X射线晶体学或NMR分析确定所获得的加合物的立体化学。Diels-Alder反应的立体选择性基于二烯与亲二烯体之间分子轨道的相互作用。估计了这些Diels–Alder反应的反应性，并讨论了该反应的一般性。
• One-pot dehydrogenation of carboxylic acid derivatives to α,β-unsaturated carbonyl compounds under mild conditions
  作者：Jun-ichi Matsuo、Yayoi Aizawa

  DOI：10.1016/j.tetlet.2004.11.106

  日期：2005.1

  Carboxylic acid derivatives such as N-acyl-2-oxazolidones, δ-lactones, and δ-lactams were smoothly dehydrogenated to the corresponding α,β-unsaturated carbonyl compounds in one-pot manner at −78 °C just by treating their lithium enolates with N-tert-butylbenzenesulfinimidoyl chloride.

  仅通过处理它们的烯醇锂，即可在-78°C下以锅法将N-酰基-2-恶唑烷酮，δ-内酯和δ-内酰胺等羧酸衍生物平稳脱氢为相应的α，β-不饱和羰基化合物。与ñ -叔-butylbenzenesulfinimidoyl酰氯。
• Catalytic Selective Oxyamidation of Cyclic Enamides using Nitrenes
  作者：Nicolas Gigant、Geoffroy Dequirez、Pascal Retailleau、Isabelle Gillaizeau、Philippe Dauban

  DOI：10.1002/chem.201102302

  日期：2012.1.2

  Yes, nitrenes did “N,O”! Intermolecular addition of nitrene to enecarbamates and enesulfonamides gives oxyamidated products in excellent yields of up to 98 % and with good levels of stereoselectivity. Complete regioselectivity is also observed, leading to the formation of N,O‐acetals which can further react with various nucleophiles under acidic conditions (see scheme; TcesNH2=trichloroethylsulfamate)

  是的，氮烯做了“ N，O”！在烯氨基甲酸酯和烯磺酰胺中分子间加成氮，可以使酰胺化的产物具有高达98％的优良收率和良好的立体选择性。还观察到完全的区域选择性，导致N，O-缩醛的形成，其可以在酸性条件下与各种亲核试剂进一步反应（参见方案； TcesNH 2 =三氯乙基氨基磺酸盐）。
• Intermolecular Rhodium(II)-Catalyzed Allylic C(<i>sp</i> ³ )-H Amination of Cyclic Enamides
  作者：Romain Rey-Rodriguez、Grégory Jestin、Vincent Gandon、Gwendal Grelier、Pascal Retailleau、Benjamin Darses、Philippe Dauban、Isabelle Gillaizeau

  DOI：10.1002/adsc.201701188

  日期：2018.2.1

  The intermolecular rhodium(II)‐catalyzed C(sp3)–H amination of enamides gives access to new 4‐aminopiperidine derivatives that are useful building blocks in medicinal chemistry. This efficient transformation proceeds at room temperature with complete regio‐ and chemoselectivity in favor of the allylic C(sp3)–H bond, and has a broad functional group tolerance. In addition, the matched combination of

  分子间的铑（II）催化的酰胺的C（sp 3）-H胺化作用使人们能够获得新的4-氨基哌啶衍生物，这些衍生物在药物化学中是有用的。这种有效的转变在室温下进行，具有完全的区域选择性和化学选择性，有利于烯丙基C（sp 3）–H键，并且具有宽泛的官能团耐受性。此外，手性配合物Rh 2（S- nta）4 [ nta =（S）-N -1,8-萘甲丙氨酸]与光学纯的（S）-磺酰亚胺酰胺的匹配组合可分离出具有优异性能的烯丙基胺。立体声控制。
• Construction of Nitrogen-Fused Tetrahydroquinolines via a Domino Reaction
  作者：Nicolas Gigant、Isabelle Gillaizeau

  DOI：10.1021/ol3020732

  日期：2012.9.7

  An efficient domino approach for the diastereoselective synthesis of polyfunctionalized nitrogen-fused tetrahydroquinoline frameworks under mild conditions has been developed. The scope and limitation of this transformation were investigated by using a range of readily accessible enamides and benzyl azides. This method is also applicable to the formation of 2,3-functionalized enamides.