(2R*,3R*)-1,2-diphenyl-3-aminoazetidine | 95242-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: (2R*,3R*)-1,2-diphenyl-3-aminoazetidine
• 英文别名: 1,2-Diphenylazetidin-3-amine；1,2-diphenylazetidin-3-amine
• CAS: 95242-71-0
• 化学式: C₁₅H₁₆N₂
• 分子量: 224.305
• InChiKey: VVQBLBPWBQUFOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-吖丁啶酮,3-叠氮-1,4-二苯基- 在 chlorohydroalane 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以90%的产率得到(2R*,3R*)-1,2-diphenyl-3-aminoazetidine
  参考文献：
  名称：

  Ojima, Iwao; Shimizu, Nobuko; Qiu, Xiaogang, Bulletin de la Societe Chimique de France, 1987, # 5, p. 649 - 658

  摘要：

  DOI：

文献信息

• Azetidines and bisazetidines. Their synthesis and use as the key intermediates to enantiomerically pure diamines, amino alcohols, and polyamines
  作者：Iwao Ojima、Mangzhu Zhao、Takehiko Yamato、Kazuaki Nakahashi、Mitsuo Yamashita、Rumiko Abe

  DOI：10.1021/jo00018a012

  日期：1991.8

  Highly selective reductions of beta-lactams (1, 5), direct-tandem bis-beta-lactams (6), and tandem bis-beta-lactams (7) to the corresponding azetidines (13, 14) and bisazetidines (11, 12) are successfully performed by using diisobutylaluminum hydride (DIBAL-H), monochlorohydroalane (AlH2Cl) and dichloroalane (AlHCl2) as specific reducing agents: Enantiomerically pure azetidines and bisazetidines are readily synthesized without loss of enantiomeric purity. Possible mechanisms that can accommodate the unique selectivity realized by hydroalanes are discussed. Hydrogenolysis of 2-arylazetidines and 2,2'-diarylbisazetidines on palladium catalyst or Raney-Ni gives the corresponding diamines, amino alcohols, polyamino alcohols, and polyamino ethers in excellent yields, which may serve as useful chiral chelating agents as well as chiral building blocks for organic synthesis and for chiral macrocycles.
• Ojima, Iwao; Shimizu, Nobuko; Qiu, Xiaogang, Bulletin de la Societe Chimique de France, 1987, # 5, p. 649 - 658
  作者：Ojima, Iwao、Shimizu, Nobuko、Qiu, Xiaogang、Chen, Hauh-Jyun C.、Nakahashi, Kazuaki

  DOI：——

  日期：——