2,5-吡咯烷二酮,1-[2-(3,4-二甲氧苯基)乙基]-3,4-二羟基-,(3R,4R)- | 187393-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-吡咯烷二酮,1-[2-(3,4-二甲氧苯基)乙基]-3,4-二羟基-,(3R,4R)-
• 英文名称: (2R,3R)-3,4-dihydroxy-1-[2-(3,4-dimethoxyphenyl)ethyl]pyrrolidine-2,5-dione
• 英文别名: (3R,4R)-1-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydroxypyrrolidine-2,5-dione
• CAS: 187393-44-8
• 化学式: C₁₄H₁₇NO₆
• 分子量: 295.292
• InChiKey: KTUFVFGTYGMEBM-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-吡咯烷二酮,1-[2-(3,4-二甲氧苯基)乙基]-3,4-二羟基-,(3R,4R)- 在 三氟乙酸 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1S,2R,10bS)-1,2-dihydroxy-8,9-dimethoxy-10b-phenyl-1,2,5,6-tetrahydropyrrolo[2,1-a]isoquinolin-3-one
  参考文献：
  名称：

  Diastereoselective synthesis of 10b-substituted hexahydropyrroloisoquinolines from l-tartaric acid. Creation of a quaternary carbon stereocentre via N-acyliminium ion cyclization

  摘要：

  A simple, three-step synthesis of 10b-substituted-hexahydropyrroloisoquinolines 12-17 starting from an L-tartaric acid derived imide is described. The methodology presented employs the addition of a Grignard reagent to the imide carbonyl group, followed by a one-pot acetylation-cyclization sequence. The crucial step, an acid-catalyzed carbon-carbon bond forming reaction via an N-acyliminium ion offers moderate to high stereoselectivity, which has been shown to be strongly dependent on the size of the R-substituent. The mixtures of pyrroloisoquinolines obtained can be separated as enantiomerically pure 2-silyloxy-derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.036
• 作为产物：
  描述：

  L-酒石酸 、 3,4-二甲氧基苯乙胺 以 xylene 为溶剂， 反应 4.0h， 以95%的产率得到2,5-吡咯烷二酮,1-[2-(3,4-二甲氧苯基)乙基]-3,4-二羟基-,(3R,4R)-
  参考文献：
  名称：

  通过非对映选择性N-酰基酰亚胺离子环化反应合成新型四环杂环呋喃[3'，2'：2,3]吡咯并[ 2,1- a ]异喹啉衍生物的两种对映体

  摘要：

  四环异喹啉衍生物（-）- 2和（+）- 2的两种对映体的有效合成分别从L-苹果酸和L-酒石酸开始。关键步骤是使用手性酰胺的非对映选择性N-酰基离子环化，在环连接处立体选择性引入季碳中心（1、3）。

  DOI：

  10.1016/s0040-4020(96)01179-9

文献信息

• 10b-Substituted hexahydropyrrolo-isoquinolines: studies on diastereoselective formation of a quaternary carbon stereocenter via N-acyliminium ion cyclization
  作者：Zbigniew Kałuża、Danuta Mostowicz、Grzegorz Dołęga、Katarzyna Mroczko、Robert Wójcik

  DOI：10.1016/j.tet.2005.10.028

  日期：2006.1

  The stereoselective synthesis of hexahydro-pyrroloisoquinolines with a quaternary carbon stereocenter is described. The presented methodology employs the addition of a Grignard reagent to the carbonyl group of imide 1, derived from l-tartaric acid, followed by acetylation and BF3·Et2O induced cyclization. The acetylation–cyclization sequence can be run either as a one-pot process, or stepwise in a

  描述了具有季碳立体中心的六氢-吡咯并异喹啉的立体选择性合成。所提出的方法采用了将格氏试剂添加到衍生自1-酒石酸的酰亚胺1的羰基上，然后进行乙酰化和BF 3 ·Et 2 O诱导的环化。乙酰化-环化顺序既可以一锅法进行，也可以在选定的溶剂中逐步进行。关键步骤是通过N-酰亚胺离子进行酸催化的碳-碳键形成反应，可提供高的立体选择性，这已证明与R 1的大小密切相关。取代基和反应条件，即溶剂的选择，路易斯酸的量，温度和底物的浓度。基于观察到的结果，提出了经由N-酰基亚胺阳离子参与溶剂的环化。
• Asymmetric synthesis of both enantiomers of novel tetracyclic heterocycle, furo[3′,2′:2,3]pyrrolo[2,1-a]isoquinoline derivative via a diastereoselective N-acyliminium ion cyclization
  作者：Jae Yeol Lee、Yong Sup Lee、Bong Young Chung、Hokoon Park

  DOI：10.1016/s0040-4020(96)01179-9

  日期：1997.2

  An efficient synthesis of both enantiomers of tetracyclic isoquinoline derivative (−)-2 and (+)-2 was accomplished starting from L-malic acid and L-tartaric acid, respectively. The key step is the stereoselective introduction of quaternary carbon-center in ring juncture using a diastereoselective N-acyliminium ion cyclization of chiral enamides (1, 3).

  四环异喹啉衍生物（-）- 2和（+）- 2的两种对映体的有效合成分别从L-苹果酸和L-酒石酸开始。关键步骤是使用手性酰胺的非对映选择性N-酰基离子环化，在环连接处立体选择性引入季碳中心（1、3）。
• Diastereoselective synthesis of 10b-substituted hexahydropyrroloisoquinolines from l-tartaric acid. Creation of a quaternary carbon stereocentre via N-acyliminium ion cyclization
  作者：Danuta Mostowicz、Robert Wójcik、Grzegorz Dołęga、Zbigniew Kałuża

  DOI：10.1016/j.tetlet.2004.06.036

  日期：2004.7

  A simple, three-step synthesis of 10b-substituted-hexahydropyrroloisoquinolines 12-17 starting from an L-tartaric acid derived imide is described. The methodology presented employs the addition of a Grignard reagent to the imide carbonyl group, followed by a one-pot acetylation-cyclization sequence. The crucial step, an acid-catalyzed carbon-carbon bond forming reaction via an N-acyliminium ion offers moderate to high stereoselectivity, which has been shown to be strongly dependent on the size of the R-substituent. The mixtures of pyrroloisoquinolines obtained can be separated as enantiomerically pure 2-silyloxy-derivatives. (C) 2004 Elsevier Ltd. All rights reserved.