N-(N-Boc-4-piperidylidene)isopropanesulfinamide | 1404231-71-5

• 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: N-(N-Boc-4-piperidylidene)isopropanesulfinamide
• 英文别名: Tert-butyl 4-propan-2-ylsulfinyliminopiperidine-1-carboxylate；tert-butyl 4-propan-2-ylsulfinyliminopiperidine-1-carboxylate
• CAS: 1404231-71-5
• 化学式: C₁₃H₂₄N₂O₃S
• 分子量: 288.411
• InChiKey: BFIIGTCLFFNQSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  78.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(N-Boc-4-piperidylidene)isopropanesulfinamide 、 tri-o-tolylboroxine 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,2-diphenylphosphinobenzene 、 sodium ethanolate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 以10%的产率得到Tert-butyl 4-(2-methylphenyl)-4-(propan-2-ylsulfinylamino)piperidine-1-carboxylate
  参考文献：
  名称：

  Rh-Catalyzed Addition of Arylboroxines to Cyclic N-(Isopropanesulfinyl)ketimines

  摘要：

  Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.

  DOI：

  10.1021/jo301634y
• 作为产物：
  描述：

  propane-2-sulfinamide 、 N-叔丁氧羰基-4-哌啶酮 在 titanium(IV) isopropylate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以75%的产率得到N-(N-Boc-4-piperidylidene)isopropanesulfinamide
  参考文献：
  名称：

  Rh-Catalyzed Addition of Arylboroxines to Cyclic N-(Isopropanesulfinyl)ketimines

  摘要：

  Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.

  DOI：

  10.1021/jo301634y

文献信息

• Rh-Catalyzed Addition of Arylboroxines to Cyclic <i>N</i>-(Isopropanesulfinyl)ketimines
  作者：Hyung Hoon Jung、Andrew W. Buesking、Jonathan A. Ellman

  DOI：10.1021/jo301634y

  日期：2012.11.2

  Arylboroxines, which are easily accessed by drying commercially available arylboronic acids, are added to N-(isopropanesulfinyl)ketimines derived from cyclohexanone, N-Boc-piperidin-4-one, and tetrahydropyran-4-one in high yields and with excellent functional group compatibility via rhodium catalysis. These results contrast with additions to the corresponding ketimines incorporating the larger N-tert-butanesulfinyl group, which give considerably lower yields. Efficient two-step preparation of racemic isopropanesulfinamide from inexpensive isopropyl disulfide and recycling of the isopropanesulfinyl group from the addition products are also described.