(-)-tert-butyl (2S,3R)-1-benzyl-2-phenylazetidine-3-carboxylate | 1394979-19-1

• 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: (-)-tert-butyl (2S,3R)-1-benzyl-2-phenylazetidine-3-carboxylate
• 英文别名: tert-butyl (2S,3R)-1-benzyl-2-phenylazetidine-3-carboxylate
• CAS: 1394979-19-1
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: APWFCNVSBPBCKZ-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3,2-二噁唑噻吩-2,2-二氧化物 、 tert-butyl cinnamate 、 lithium N-benzyltrimethylsilylamide 在 (1S,2S)-1,2-dimethoxy-1,2-diphenylethane 作用下， 以 甲苯 为溶剂， 反应 2.21h， 以82%的产率得到(-)-tert-butyl (2S,3R)-1-benzyl-2-phenylazetidine-3-carboxylate
  参考文献：
  名称：

  General Entry to Asymmetric One-Pot [N + 2 + n] Cyclization for the Synthesis of Three- to Seven-Membered Azacycloalkanes

  摘要：

  Enantio- and diastereoselective one-pot synthesis of three- to seven-membered cis-azaheterocycles was achieved using a triggered asymmetric conjugate addition reaction of lithium amide with an enoate, followed by alkylation of the resulting lithium enolate with alpha,omega-dihaloalkane and N-alkylation. Isomerization of cis-azaheterocycles with a base yielded the trans-product, constituting a one-pot synthesis of cis-azacycles and a two-step synthesis of trans-azacycles. The four-step asymmetric synthesis of nemonapride highlights the general utility of the method.

  DOI：

  10.1021/jo301495a

文献信息

• General Entry to Asymmetric One-Pot [<i>N</i> + 2 + <i>n</i>] Cyclization for the Synthesis of Three- to Seven-Membered Azacycloalkanes
  作者：Shingo Harada、Takeo Sakai、Kiyosei Takasu、Ken-ichi Yamada、Yasutomo Yamamoto、Kiyoshi Tomioka

  DOI：10.1021/jo301495a

  日期：2012.9.7

  Enantio- and diastereoselective one-pot synthesis of three- to seven-membered cis-azaheterocycles was achieved using a triggered asymmetric conjugate addition reaction of lithium amide with an enoate, followed by alkylation of the resulting lithium enolate with alpha,omega-dihaloalkane and N-alkylation. Isomerization of cis-azaheterocycles with a base yielded the trans-product, constituting a one-pot synthesis of cis-azacycles and a two-step synthesis of trans-azacycles. The four-step asymmetric synthesis of nemonapride highlights the general utility of the method.