tert-butyl 2-benzyl-5-methyl-1H-pyrrole-1-carboxylate | 180516-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: tert-butyl 2-benzyl-5-methyl-1H-pyrrole-1-carboxylate
• 英文别名: Tert-butyl 2-benzyl-5-methylpyrrole-1-carboxylate
• CAS: 180516-67-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: RERXRTYNWUSGJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-benzyl-5-methyl-1H-pyrrole-1-carboxylate 在 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以46%的产率得到2-benzyl-5-methylpyrrole
  参考文献：
  名称：

  A General Synthesis of Pyrroles and Fused Pyrrole Systems from Ketones and Amino Acids

  摘要：

  The lithium enolates of ketones react with BOC-alpha-amino aldehydes and BOC-alpha-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from ol-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.

  DOI：

  10.1021/jo960401q
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 tert-butyl 2-benzyl-5-methyl-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  A General Synthesis of Pyrroles and Fused Pyrrole Systems from Ketones and Amino Acids

  摘要：

  The lithium enolates of ketones react with BOC-alpha-amino aldehydes and BOC-alpha-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from ol-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.

  DOI：

  10.1021/jo960401q

文献信息

• A Facile Access to Pyrroles from Amino Acids via an Aza-Wacker Cyclization
  作者：Zuhui Zhang、Jintang Zhang、Jiajing Tan、Zhiyong Wang

  DOI：10.1021/jo800433b

  日期：2008.7.1

  A facile and efficient synthesis of pyrroles from readily available amino acids is described. The key step in the method is an aza-Wacker oxidative cyclization catalyzed by palladium(II)/Cu(OTf)2. A series of pyrroles were obtained by this method under mild conditions.

  描述了从容易获得的氨基酸容易且有效地合成吡咯的方法。该方法的关键步骤是钯（II）/ Cu（OTf）2催化的氮杂-瓦克氧化环化反应。通过该方法在温和的条件下获得了一系列吡咯。
• An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols
  作者：Luiz C. Dias、Juliana Fattori、Carla C. Perez、Vanda M. de Oliveira、Andrea M. Aguilar

  DOI：10.1016/j.tet.2008.04.049

  日期：2008.6

  AWe wish to describe here the diastereoselective reaction between chiral N-Boc-alpha-amino aldehydes with both achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-alpha-amino alcohols, which are easily converted to the corresponding 4-N-Boc-amino-3-hydroxy ketones after treatment with catalytic amounts of OsO4 in the presence of NaIO4. After reduction of the carbonyl function, these 4-N-Boc-amino-3-hydroxy ketones were converted to 1-deoxy-5-hydroxy sphingosine analogues. (C) 2008 Elsevier Ltd. All rights reserved.
• A Facile Synthesis of N-Boc-Protected Pyrroles by Cyclodehydration of γ-Amino-α,β-enals and -enones
  作者：Olivier Paulus、Gilles Alcaraz、Michel Vaultier

  DOI：10.1002/1099-0690(200208)2002:15<2565::aid-ejoc2565>3.0.co;2-i

  日期：2002.8

  A novel series of N-Boc-substituted and fused pyrroles was prepared by cyclodehydration of readily accessible (E)-gamma-(tert-butoxycarbonylamino)-alpha,beta-enals and -enones. Functionalisation of the pyrrole ring was then explored with 2-borylated pyrroles in the Suzuki-Miyaura coupling.