(2R,3R)-1-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-trimethylsilanyloxy-pyrrolidine-2,5-dione | 749922-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-1-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-trimethylsilanyloxy-pyrrolidine-2,5-dione
• 英文别名: (3R,4R)-1-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-bis(trimethylsilyloxy)pyrrolidine-2,5-dione
• CAS: 749922-52-9
• 化学式: C₂₀H₃₃NO₆Si₂
• 分子量: 439.656
• InChiKey: RYXNOPCKVPDQSK-QZTJIDSGSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  491.0±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-trimethylsilanyloxy-pyrrolidine-2,5-dione 在 三氟乙酸 作用下， 以 四氢呋喃 、 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：

  三甲基氯硅烷 、 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 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以94%的产率得到(2R,3R)-1-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-trimethylsilanyloxy-pyrrolidine-2,5-dione
  参考文献：
  名称：

  10b取代的六氢吡咯并异喹啉：通过N-酰基亚胺离子环化非选择性形成季碳立体中心的研究

  摘要：

  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。

  DOI：

  10.1016/j.tet.2005.10.028

文献信息

• C2-Symmetric hemiaminal ethers and diamines: new ligands for copper-catalyzed desymmetrization of meso-1,2-diols and asymmetric Henry reactions
  作者：Zbigniew Kałuża、Krzysztof Bielawski、Rafał Ćwiek、Piotr Niedziejko、Przemysław Kaliski

  DOI：10.1016/j.tetasy.2013.09.011

  日期：2013.11

  The synthesis of novel, enantiomerically pure C2-symmetrical hemiaminal ethers and diamines containing piperazine core is presented. The key steps of the synthesis involve the dimerization of an in situ generated α-amino aldehyde into the corresponding cyclic bis-hemiaminal, followed by dehydration in the presence of a base to give a 7-oxa-2,5-diaza-bicyclo[2.2.1]heptane derivative, which can be regarded

  提出了新颖的，对映体纯的含哌嗪核心的对映体纯的C 2对称半氨基醚和二胺的合成。合成的关键步骤包括将原位生成的α-氨基醛二聚为相应的环状双半缩醛，然后在碱存在下脱水，得到7-oxa-2,5-diaza-bicyclo [ 2.2.1]庚烷衍生物，可以视为双环双半缩醛内醚。这些化合物代表了一类新的分子，首次明确地建立了结构。最后，三乙酰氧基-硼氢化钠还原得到相应的二胺。这两类化合物，即新的二胺和半氨基醚，均被证明是铜（II）催化的内消旋对称化的良好配体。-二醇（高达87％ee）和亨利反应（高达84％ee）。
• Heck Cyclization Strategy for Preparation of Erythrinan Alkaloids: Asymmetric Synthesis of Unnatural (−)-Erysotramidine from <scp>L</scp>-Tartaric Acid
  作者：Danuta Mostowicz、Mirosław Dygas、Zbigniew Kałuża

  DOI：10.1021/jo5026157

  日期：2015.2.6

  was synthesized for the first time. The synthesis features the use of the enantiopure synthon, prepared in a set of highly stereoselective reactions, including N-acyliminium cyclization, dihydrofuranyl ring formation via silver-catalyzed intramolecular alcohol addition to acetylene, and vinyl ether catalytic hydrogen reduction. The crucial step of the synthesis, assembly of ring A, was achieved by using

  与衍生自一种酰亚胺升酒石酸作为起始原料，耳鼻喉科-erysotramidine是首次合成的。合成的特征是使用对映纯合成子，该合成子是在一组高度立体选择性的反应中制得的，包括N-酰基lim基环化，通过银催化的分子内醇加成乙炔形成二氢呋喃基环，以及乙烯基醚催化的氢还原反应。合成的关键步骤，即环A的组装是通过使用（Z）-碘代烯烃的Heck环化来实现的。
• 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.
• 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。