tert-butyl 1-benzyl-3-phenylaziridine-2-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 1-benzyl-3-phenylaziridine-2-carboxylate
• 英文别名: Tert-butyl 1-benzyl-3-phenylaziridine-2-carboxylate
• 化学式: C₂₀H₂₃NO₂
• 分子量: 309.408
• InChiKey: BYAHCNVSHDCSRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 tert-butyl 1-benzyl-3-phenylaziridine-2-carboxylate 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以91%的产率得到tert-butyl (R)-2-tert-butoxycarbonylamino-3-phenylpropanoate
  参考文献：
  名称：

  胍基内酯介导的亚芳基叠氮化：未活化的3-芳基氮杂环丁烷-2-羧酸盐形成的范围和局限性

  摘要：

  摘要 讨论了由芳基醛产生的未活化的3-芳基氮丙啶-2-羧酸酯的芳基醛介导的啶基lide啶化的范围和局限性，适用于不对称合成。 讨论了由芳基醛产生的未活化的3-芳基氮丙啶-2-羧酸酯的芳基醛介导的啶基lide啶化的范围和局限性，适用于不对称合成。

  DOI：

  10.1055/s-0033-1341233
• 作为产物：
  描述：

  1-氯-2-碘乙烷 、 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 3.5h， 以97%的产率得到
  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

• Guanidinium Ylide Mediated Aziridination from Arylaldehydes: Scope and Limitations in the Formation of Unactivated 3-Arylaziridine-2-carboxylates
  作者：Tsutomu Ishikawa、Yukiko Oda、Kihito Hada、Marie Miyata、Chisato Takahata、Yukiko Hayashi、Masato Takahashi、Naoki Yajima、Makiko Fujinami

  DOI：10.1055/s-0033-1341233

  日期：——

  Abstract The scope and limitations of guanidinium ylide mediated aziridinations from arylaldehydes yielding unactivated 3-arylaziridine-2-carboxylates, applicable to asymmetric synthesis, are discussed. The scope and limitations of guanidinium ylide mediated aziridinations from arylaldehydes yielding unactivated 3-arylaziridine-2-carboxylates, applicable to asymmetric synthesis, are discussed.

  摘要 讨论了由芳基醛产生的未活化的3-芳基氮丙啶-2-羧酸酯的芳基醛介导的啶基lide啶化的范围和局限性，适用于不对称合成。 讨论了由芳基醛产生的未活化的3-芳基氮丙啶-2-羧酸酯的芳基醛介导的啶基lide啶化的范围和局限性，适用于不对称合成。
• 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.