1-O-tert-butyl 5-O-propan-2-yl 5-[hydroxy-(1-methylpyrrol-2-yl)methyl]-2H-pyrrole-1,5-dicarboxylate | 263408-00-0

• 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: 1-O-tert-butyl 5-O-propan-2-yl 5-[hydroxy-(1-methylpyrrol-2-yl)methyl]-2H-pyrrole-1,5-dicarboxylate
• CAS: 263408-00-0
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: LBPPVUXJNXOINQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  81
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyl 5-O-propan-2-yl 5-[hydroxy-(1-methylpyrrol-2-yl)methyl]-2H-pyrrole-1,5-dicarboxylate 在 水 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到1-O-tert-butyl 5-O-propan-2-yl 5-(1-methylpyrrole-2-carbonyl)-2H-pyrrole-1,5-dicarboxylate
  参考文献：
  名称：

  Reductive aldol reactions on aromatic heterocycles

  摘要：

  The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02224-8
• 作为产物：
  描述：

  吡咯-2-羧酸 在 草酰氯 、 lithium 作用下， 以 四氢呋喃 、 氨 为溶剂， 生成 1-O-tert-butyl 5-O-propan-2-yl 5-[hydroxy-(1-methylpyrrol-2-yl)methyl]-2H-pyrrole-1,5-dicarboxylate
  参考文献：
  名称：

  Reductive aldol reactions on aromatic heterocycles

  摘要：

  The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02224-8

文献信息

• Reductive aldol reactions on aromatic heterocycles
  作者：Timothy J Donohoe、Karl W Ace、Paul M Guyo、Madeleine Helliwell、Jeffrey McKenna

  DOI：10.1016/s0040-4039(99)02224-8

  日期：2000.2

  The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd. All rights reserved.