[(4S)-7-(4-methylphenyl)sulfonyl-4-propan-2-yl-7-azabicyclo[4.1.0]heptan-1-yl]methanol

• 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: [(4S)-7-(4-methylphenyl)sulfonyl-4-propan-2-yl-7-azabicyclo[4.1.0]heptan-1-yl]methanol
• 化学式: C₁₇H₂₅NO₃S
• 分子量: 323.456
• InChiKey: FATPMLBWIOPJBY-BMWKDGKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4S)-7-(4-methylphenyl)sulfonyl-4-propan-2-yl-7-azabicyclo[4.1.0]heptan-1-yl]methanol 在 邻苯二甲酸二甲酯 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到(4S)-4-isopropyl-7-tosyl-7-azabicyclo[4.1.0]heptane-1-carbaldehyde
  参考文献：
  名称：

  Tetrasubstituted Pyrrolidines via a Tandem Aza-Payne/Hydroamination Reaction

  摘要：

  A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination.

  DOI：

  10.1021/ja068077w
• 作为产物：
  描述：

  (S)-(-)-紫苏醇 在 Adam’s catalyst N-溴代丁二酰亚胺(NBS) 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 [(4S)-7-(4-methylphenyl)sulfonyl-4-propan-2-yl-7-azabicyclo[4.1.0]heptan-1-yl]methanol
  参考文献：
  名称：

  Tetrasubstituted Pyrrolidines via a Tandem Aza-Payne/Hydroamination Reaction

  摘要：

  A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination.

  DOI：

  10.1021/ja068077w

文献信息

• Diastereomerically and Enantiomerically Pure 2,3-Disubstituted Pyrrolidines from 2,3-Aziridin-1-ols Using a Sulfoxonium Ylide:  A One-Carbon Homologative Relay Ring Expansion
  作者：Jennifer M. Schomaker、Somnath Bhattacharjee、Jun Yan、Babak Borhan

  DOI：10.1021/ja065833p

  日期：2007.2.1

  An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of

  2,3-氮丙啶-1-醇的基于叶立德的氮杂-佩恩重排导致制备吡咯烷的有效方法。碱性反应条件下的氮杂-佩恩重排有利于环氧胺的形成。随后环氧化物被叶立德亲核攻击产生双阴离子，在 5-exo-tet 闭环后产生所需的吡咯烷，从而完成三元到五元含氮环系统的接力. 这个过程发生在立体化学保真度完全转移的情况下，可以应用于空间位阻的氮丙啶醇。
• Synthesis of N-heterocycles, beta-amino acids, and allyl amines via aza-payne mediated reaction of ylides and hydroxy aziridines
  申请人：Borhan Babak

  公开号：US20090012120A1

  公开（公告）日：2009-01-08

  An ylide-based aza-Payne rearrangement of 2,3-aziridin- 1 -ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under the basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring closure yields the desired pyrrolidine, thus completing the relay of the 3-membered the 5-membered nitrogen containing ring system. This process takes place with complete transfer of stereochemical fidelity, and can be applied to sterically hindered aziridinols.

  基于叶立德的2,3-氮杂环丙醇的aza-Payne重排反应导致了一种高效的吡咯烷制备过程。在碱性反应条件下进行的aza-Payne重排有利于环氧胺的形成。叶立德对环氧化物的亲核攻击产生双阴离子，随后通过5-内攻环闭合产生所需的吡咯烷，从而完成了含3-成员和5-成员氮环的环的传递。这个过程完全保持立体化学的保真度，并可应用于立体位阻的氮杂环丙醇。
• Tetrasubstituted Pyrrolidines via a Tandem Aza-Payne/Hydroamination Reaction
  作者：Jennifer M. Schomaker、Andrea R. Geiser、Rui Huang、Babak Borhan

  DOI：10.1021/ja068077w

  日期：2007.4.1

  A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination.