1-tert-butyl 3-methyl 3-(3,4-dihydroxy-5-methoxyphenyl)-2-oxopyrrolidine-1,3-dicarboxylate | 1397496-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-tert-butyl 3-methyl 3-(3,4-dihydroxy-5-methoxyphenyl)-2-oxopyrrolidine-1,3-dicarboxylate
• 英文别名: 1-O-tert-butyl 3-O-methyl 3-(3,4-dihydroxy-5-methoxyphenyl)-2-oxopyrrolidine-1,3-dicarboxylate
• CAS: 1397496-03-5
• 化学式: C₁₈H₂₃NO₈
• 分子量: 381.383
• InChiKey: MNAAUNYGWGRGGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  溴氯甲烷 、 1-tert-butyl 3-methyl 3-(3,4-dihydroxy-5-methoxyphenyl)-2-oxopyrrolidine-1,3-dicarboxylate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以2.03 g的产率得到1-tert-butyl 3-methyl 3-(7-methoxybenzo[d][1,3]dioxol-5-yl)-2-oxopyrrolidine-1,3-dicarboxylate
  参考文献：
  名称：

  （±）-鲍威尔碱和（±）-丁香碱的全合成

  摘要：

  （±）-鲍威尔碱（13个线性步骤，总产率为6％）和（±）-布啡啶碱（14个线性步骤，总产率为6％）的总合成，并已使用一种新的方法制备了克力烷骨架。有机催化氧化偶合可以高产率直接构建关键的季碳-芳基键，从而可以快速进入目标生物碱。

  DOI：

  10.1021/ol1000654
• 作为产物：
  描述：

  在 sodium dithionite 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 1-tert-butyl 3-methyl 3-(3,4-dihydroxy-5-methoxyphenyl)-2-oxopyrrolidine-1,3-dicarboxylate
  参考文献：
  名称：

  An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine

  摘要：

  Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (+/-)-powelline and (+/-)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.132

文献信息

• Laccase-catalysed α-arylation of cyclic β-dicarbonyl compounds
  作者：Jörg Pietruszka、Chuan Wang

  DOI：10.1039/c2gc35662g

  日期：——

  In this protocol we described an environmentally friendly synthesis of α-arylated cyclic β-dicarbonyl compounds employing various catechols as precursors through an oxidation/Michael addition sequence. The process proceeded under the catalysis of a commercially available laccase at room temperature with the use of aerial oxygen as the oxidant affording the products in moderate to excellent yields (36–96%)

  在该协议中，我们描述了一种环境友好的合成α-芳基化环状β-二羰基化合物的方法， 儿茶酚通过氧化/迈克尔加成序列作为前体。该过程在室温下使用市售漆酶的催化下进行，使用空气中的氧气作为氧化剂，可提供中等至极佳收率的产品（36-96％）。此外，高度功能化环戊烷通过芳基化以优异的非对映选择性（dr> 99 ：1，95％ee）合成了一个全碳四元立体中心的轴承。
• Oxidative cross-coupling reaction of catechols with active methylene compounds in an aqueous medium using an AlPO₄-supported Ru catalyst
  作者：Zen Maeno、Masanobu Yamamoto、Takato Mitsudome、Tomoo Mizugaki、Koichiro Jitsukawa

  DOI：10.1039/c8cy01425f

  日期：——

  A green oxidative coupling reaction of catechols with active methylene compounds was achieved using an AlPO4-supported Ru catalyst, where O2 and H2O were used as the ideal oxidant and solvent, respectively. The catalyst is easily separable, reusable and applicable for gram-scale syntheses.

  使用AlPO 4负载的Ru催化剂可实现邻苯二酚与活性亚甲基化合物的绿色氧化偶联反应，其中O 2和H 2 O分别用作理想的氧化剂和溶剂。该催化剂易于分离，可重复使用并可用于克级合成。
• Total Synthesis of (±)-Powelline and (±)-Buphanidrine
  作者：Katherine M. Bogle、David J. Hirst、Darren J. Dixon

  DOI：10.1021/ol1000654

  日期：2010.3.19

  The total synthesis of (±)-powelline (13 linear steps in an overall yield of 6%) and (±)-buphanidrine (14 linear steps and a 6% overall yield) and has been achieved using a novel approach to the crinane skeleton. An organocatalytic oxidative coupling allowed direct construction of the key quaternary carbon-to-aryl bond in high yield allowing rapid access to the target alkaloids.

  （±）-鲍威尔碱（13个线性步骤，总产率为6％）和（±）-布啡啶碱（14个线性步骤，总产率为6％）的总合成，并已使用一种新的方法制备了克力烷骨架。有机催化氧化偶合可以高产率直接构建关键的季碳-芳基键，从而可以快速进入目标生物碱。
• An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine
  作者：Katherine M. Bogle、David J. Hirst、Darren J. Dixon

  DOI：10.1016/j.tet.2010.04.132

  日期：2010.8

  Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (+/-)-powelline and (+/-)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. (C) 2010 Elsevier Ltd. All rights reserved.