(R)-tert-butyl 4-benzyl-2-(benzyloxymethyl)-3,4-dihydropyrazine-1(2H)-carboxylate | 1223471-40-6

• 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: (R)-tert-butyl 4-benzyl-2-(benzyloxymethyl)-3,4-dihydropyrazine-1(2H)-carboxylate
• 英文别名: (S)-tert-butyl 2-isopropyl-4-benzyl-3,4-dihydro-pyrazine-1(2H)-carboxylate；tert-butyl (2S)-4-benzyl-2-propan-2-yl-2,3-dihydropyrazine-1-carboxylate
• CAS: 1223471-40-6
• 化学式: C₁₉H₂₈N₂O₂
• 分子量: 316.444
• InChiKey: WHMWZZSUEMQSQP-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二碘甲烷 、 (R)-tert-butyl 4-benzyl-2-(benzyloxymethyl)-3,4-dihydropyrazine-1(2H)-carboxylate 在 diethylzinc 作用下， 以 乙醚 、 正己烷 为溶剂， 以70%的产率得到(1S,3S,6R)-tert-butyl 5-benzyl-3-isopropyl-2,5-diazabicyclo[4.1.0]heptane-2-carboxylate
  参考文献：
  名称：

  Stereoselective cyclopropanation of chiral 5-substituted dihydro-2H-piperazines

  摘要：

  The Simmon-Smith cyclopropanation of enantiomerically enriched dehydropiperazines is reported. The reaction is highly stereoselective and allowed us to prepare new, enantiomerically enriched 3-substituted 2,5-diazabicyclo[4.1.0]heptane cores with high diastereomeric purity and a relative anti-configuration, which was assigned by NMR analysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.015
• 作为产物：
  描述：

  (S)-1-benzyl-4-tert-butoxycarbonyl-5-isopropyl-2-oxopiperazine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以48%的产率得到(R)-tert-butyl 4-benzyl-2-(benzyloxymethyl)-3,4-dihydropyrazine-1(2H)-carboxylate
  参考文献：
  名称：

  Synthesis of new polysubstituted piperazines and dihydro-2H-pyrazines by selective reduction of 2-oxo-piperazines

  摘要：

  New enantiomerically enriched 1,4,5-piperazines and 1,4,5-dihydro-2H-pyrazines have been prepared by reduction of the corresponding 2-oxo-piperazines. Selective reduction can be achieved by careful control of the reaction conditions using LiAlH4. Notably the two nitrogen atoms of the final compounds are orthogonally protected. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.025

文献信息

• Stereoselective cyclopropanation of chiral 5-substituted dihydro-2H-piperazines
  作者：Gianna Reginato、Maria Pia Catalani、Alessandro Mordini、Bernardo Pezzati、Andrea Bernardelli、Silvia Davalli、Nicola Pace

  DOI：10.1016/j.tetasy.2012.11.015

  日期：2013.1

  The Simmon-Smith cyclopropanation of enantiomerically enriched dehydropiperazines is reported. The reaction is highly stereoselective and allowed us to prepare new, enantiomerically enriched 3-substituted 2,5-diazabicyclo[4.1.0]heptane cores with high diastereomeric purity and a relative anti-configuration, which was assigned by NMR analysis. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of new polysubstituted piperazines and dihydro-2H-pyrazines by selective reduction of 2-oxo-piperazines
  作者：Gianna Reginato、Barbara Di Credico、Daniele Andreotti、Anna Mingardi、Alfredo Paio、Daniele Donati、Bernardo Pezzati、Alessandro Mordini

  DOI：10.1016/j.tetasy.2009.12.025

  日期：2010.2

  New enantiomerically enriched 1,4,5-piperazines and 1,4,5-dihydro-2H-pyrazines have been prepared by reduction of the corresponding 2-oxo-piperazines. Selective reduction can be achieved by careful control of the reaction conditions using LiAlH4. Notably the two nitrogen atoms of the final compounds are orthogonally protected. (C) 2010 Elsevier Ltd. All rights reserved.