1-O-tert-butyl 5-O-propan-2-yl 5-[hydroxy(phenyl)methyl]-2H-pyrrole-1,5-dicarboxylate | 263407-98-3

• 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(phenyl)methyl]-2H-pyrrole-1,5-dicarboxylate
• CAS: 263407-98-3
• 化学式: C₂₀H₂₇NO₅
• 分子量: 361.438
• InChiKey: HMIQHEYHWAOYKU-UHFFFAOYSA-N

物化性质

• 沸点：
  464.5±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.1
• 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(phenyl)methyl]-2H-pyrrole-1,5-dicarboxylate 在 cerium(III) chloride sodium tetrahydroborate 、 水 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 (1'RS,2RS)-isopropyl 1-(tert-butyloxycarbonyl)-2-[1'-hydroxy-1'-phenyl-methyl]-2,5-dihydropyrrole-2-carboxylate
  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(phenyl)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

• The partial reduction of heterocycles: an alternative to the Birch reduction
  作者：Timothy J Donohoe、Rakesh R Harji、Rick P.C Cousins

  DOI：10.1016/s0040-4039(99)02315-1

  日期：2000.2

  The partial reduction of a series of heterocycles in THF is described. By adding amine 3 as a proton source and naphthalene as an electron carrier, we were able to produce reductively alkylated pyrrolines and dihydrofurans in moderate to good yields. This reaction does not require liquid ammonia as a solvent, which may have interesting ramifications for large-scale synthesis. Moreover, we were also able to quench the reduction reactions with an acid chloride so performing a reductive acylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Diastereoselective reductive aldol reactions of Boc-protected electron deficient pyrroles
  作者：Timothy J. Donohoe、David House

  DOI：10.1016/s0040-4039(02)02672-2

  日期：2003.1

  An anti-selective reductive aldol reaction of a Boc-protected, 2-substituted pyrrole is reported. Reduction with LiDBB generates an exocyclic lithium enolate, but optimal stereoselectivity is obtained by transmetallation to magnesium with MgBr2.OEt2. The corresponding syn-aldols can easily be obtained (protected as carbamates) by subsequent inversion. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 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.