3-(diphenylmethylene)-1-(phenylsulfonyl)piperidine | 1257268-66-8

• 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: 3-(diphenylmethylene)-1-(phenylsulfonyl)piperidine
• 英文别名: 1-(Benzenesulfonyl)-3-benzhydrylidenepiperidine；1-(benzenesulfonyl)-3-benzhydrylidenepiperidine
• CAS: 1257268-66-8
• 化学式: C₂₄H₂₃NO₂S
• 分子量: 389.518
• InChiKey: HAJMKUIASPYGDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(diphenylmethylene)-1-(phenylsulfonyl)piperidine 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 5-(methoxydiphenylmethyl)-1-(phenylsulfonyl)-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  Regioselective synthesis of 2-substituted 3-diarylmethylenylpiperidines

  摘要：

  A simple three-step synthetic routes toward 2-substituted 3-diarylmethylenylpiperidines 7 (Y = CN) and 8 (Y = allyl) starting with 3-diarylmethylenylpiperidines 9 is described. The process was carried out by the bromomethoxylation of skeleton 9 with NBS in MeOH at reflux for 2 h, regioselective alpha-dehydrobromination with DBU in THF at reflux for 10 h, and BF3-OEt(2)catalyzed cross-coupling of the corresponding enamine with trimethylsilyl-based nucleophiles (TMS-Y) in DCM at rt for 2 h. alpha-Amino ester 18 and beta-amino acid 19 are also synthesized via the simple three-step synthetic protocol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.105
• 作为产物：
  描述：

  3-哌啶甲酸乙酯 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.75h， 生成 3-(diphenylmethylene)-1-(phenylsulfonyl)piperidine
  参考文献：
  名称：

  Regioselective synthesis of 2-substituted 3-diarylmethylenylpiperidines

  摘要：

  A simple three-step synthetic routes toward 2-substituted 3-diarylmethylenylpiperidines 7 (Y = CN) and 8 (Y = allyl) starting with 3-diarylmethylenylpiperidines 9 is described. The process was carried out by the bromomethoxylation of skeleton 9 with NBS in MeOH at reflux for 2 h, regioselective alpha-dehydrobromination with DBU in THF at reflux for 10 h, and BF3-OEt(2)catalyzed cross-coupling of the corresponding enamine with trimethylsilyl-based nucleophiles (TMS-Y) in DCM at rt for 2 h. alpha-Amino ester 18 and beta-amino acid 19 are also synthesized via the simple three-step synthetic protocol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.105

文献信息

• Regioselective synthesis of 2-substituted 3-diarylmethylenylpiperidines
  作者：Meng-Yang Chang、Chung-Han Lin、Tein-Wei Lee

  DOI：10.1016/j.tetlet.2011.11.105

  日期：2012.2

  A simple three-step synthetic routes toward 2-substituted 3-diarylmethylenylpiperidines 7 (Y = CN) and 8 (Y = allyl) starting with 3-diarylmethylenylpiperidines 9 is described. The process was carried out by the bromomethoxylation of skeleton 9 with NBS in MeOH at reflux for 2 h, regioselective alpha-dehydrobromination with DBU in THF at reflux for 10 h, and BF3-OEt(2)catalyzed cross-coupling of the corresponding enamine with trimethylsilyl-based nucleophiles (TMS-Y) in DCM at rt for 2 h. alpha-Amino ester 18 and beta-amino acid 19 are also synthesized via the simple three-step synthetic protocol. (C) 2011 Elsevier Ltd. All rights reserved.