(2RS)-1-(1',1'-dimethylethyl) 2-(1-methylethyl) 2-[(5''-methyl-2''-furanyl)carbonyl]-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate | 263408-03-3

• 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: (2RS)-1-(1',1'-dimethylethyl) 2-(1-methylethyl) 2-[(5''-methyl-2''-furanyl)carbonyl]-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate
• 英文别名: 1-O-tert-butyl 5-O-propan-2-yl 5-(5-methylfuran-2-carbonyl)-2H-pyrrole-1,5-dicarboxylate
• CAS: 263408-03-3
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: QCLWGWISNZZGLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2RS)-1-(1',1'-dimethylethyl) 2-(1-methylethyl) 2-[(5''-methyl-2''-furanyl)carbonyl]-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate 在 chromium chloride 、 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 生成 (1''RS,2RS)-1-(1',1'-dimethylethyl) 2-(1-methylethyl) 2-[hydroxy(5''-methyl-2''-furan)methyl]-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate 、 (1''RS,2SR)-1-(1',1'-dimethylethyl) 2-(1-methylethyl) 2-[hydroxy(5''-methyl-2''-furan)methyl]-2,5-dihydro-1H-pyrrole-1,2-dicarboxylate
  参考文献：
  名称：

  Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocyclesThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.

  摘要：

  研究发现，缺电子芳香化合物的还原醛醇反应是碳-碳键形成的一种可行方法。氨和无氨条件下的还原反应都能促进醛醇反应，但后者在与可烯化的醛反应中表现出更大的空间。此外，在无氨条件下还原可以加入路易斯酸，从而提高立体选择性，有利于反立体异构体。在部分还原完成后，可以通过两种不同方案中的一种来生产合成非对映异构体。本文的主要重点是缺电子吡咯的还原性醛醇反应，但同时也证明了苯类和呋喃类芳香化合物也适用于这种还原条件。

  DOI：

  10.1039/b306937k
• 作为产物：
  描述：

  吡咯-2-羧酸 在 草酰氯 、 水 、 lithium 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 氨 为溶剂， 生成 (2RS)-1-(1',1'-dimethylethyl) 2-(1-methylethyl) 2-[(5''-methyl-2''-furanyl)carbonyl]-2,5-dihydro-1H-pyrrole-1,2-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.
• Scope of the reductive aldol reaction: application to aromatic carbocycles and heterocyclesThis is one of a number of contributions from the current members of the Dyson Perrins Laboratory to mark the end of almost 90 years of organic chemistry research in that building, as all its current academic staff move across South Parks Road to a new purpose-built laboratory.
  作者：Timothy J. Donohoe、David House、K. W. Ace

  DOI：10.1039/b306937k

  日期：——

  The reductive aldol reaction of electron deficient aromatic compounds has been investigated and found to be a viable method for carbon–carbon bond formation. Reductions under ammonia and ammonia-free conditions were both capable of facilitating the aldol reaction although the latter showed more scope for reaction with enolisable aldehydes. Moreover, reduction under ammonia-free conditions allowed the addition of Lewis acids which improved stereoselectivity to favour the anti stereoisomer. Production of the syn diastereoisomer was possible through either one of two different protocols performed after partial reduction was complete. While the main emphasis of this paper concerns the reductive aldol reaction of electron deficient pyrroles, it was also shown that both benzenoid and furan aromatic compounds were amenable to such reducing conditions.

  研究发现，缺电子芳香化合物的还原醛醇反应是碳-碳键形成的一种可行方法。氨和无氨条件下的还原反应都能促进醛醇反应，但后者在与可烯化的醛反应中表现出更大的空间。此外，在无氨条件下还原可以加入路易斯酸，从而提高立体选择性，有利于反立体异构体。在部分还原完成后，可以通过两种不同方案中的一种来生产合成非对映异构体。本文的主要重点是缺电子吡咯的还原性醛醇反应，但同时也证明了苯类和呋喃类芳香化合物也适用于这种还原条件。