1-[(1R)-2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]tetrahydro-1H-pyrrole-2,5-dione | 406195-56-0

• 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: 1-[(1R)-2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]tetrahydro-1H-pyrrole-2,5-dione
• 英文别名: (S)-(-)-1-[2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]pyrrolidine-2,5-dione；1-[(S)-2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]pyrrolidine-2,5-dione；1-[(2S)-1-(3,4-dimethoxyphenyl)-3-hydroxypropan-2-yl]pyrrolidine-2,5-dione
• CAS: 406195-56-0
• 化学式: C₁₅H₁₉NO₅
• 分子量: 293.32
• InChiKey: QOYQSHXYMNLRRD-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-[(1R)-2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]tetrahydro-1H-pyrrole-2,5-dione 在 三氟乙酸 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 反应 32.0h， 生成 (5S,10bR)-5-(hydroxymethyl)-10b-methyl-8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3-one
  参考文献：
  名称：

  Diastereoselective Intramolecular α-Amidoalkylation Reactions of l-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinolines

  摘要：

  Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).

  DOI：

  10.1021/jo051584w
• 作为产物：
  描述：

  (S)-(-)-[2-(3,4-二甲氧基苯基)-1-羟甲基乙基]氨基甲酸叔丁酯 在 咪唑 、 四丁基氟化铵 、 sodium acetate 、 乙酸酐 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 1-[(1R)-2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]tetrahydro-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Diastereoselective Intramolecular α-Amidoalkylation Reactions of l-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinolines

  摘要：

  Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).

  DOI：

  10.1021/jo051584w

文献信息

• Stereoselective synthesis of the pyrroloisoquinoline ring system
  作者：Steven M. Allin、Stella L. James、William P. Martin、Timothy A. D. Smith、Mark R. J. Elsegood

  DOI：10.1039/b105402n

  日期：2001.11.15

  In this paper we report a facile and stereoselective approach to the pyrroloisoquinoline ring system through the application of N-acyliminium chemistry from readily available non-racemic chiral templates. The stereochemical outcome of the cyclisation reactions has been determined by NOE and X-ray crystallography. We also demonstrate the synthetic potential of our new approach through removal of the pendant hydroxymethyl auxiliary from a product of cyclisation.

  在本文中，我们报告了通过应用 N-酰亚胺化学，从容易获得的非外消旋手性模板出发，对吡咯异喹啉环系统进行简便和立体选择性研究的方法。环化反应的立体化学结果是通过 NOE 和 X 射线晶体学确定的。我们还通过去除环化反应产物中的羟甲基助剂，证明了新方法的合成潜力。
• A New Asymmetric Synthesis of the Anti-Tumor Alkaloid (<i>R</i>)-(+)-Crispine A
  作者：Steven M. Allin、Sean N. Gaskell、Joannah M. R. Towler、Philip C. Bulman Page、Basu Saha、Michael J. McKenzie、William P. Martin

  DOI：10.1021/jo071235x

  日期：2007.11.1

  We report a novel, facile, and asymmetric approach for the synthesis of the anti-tumor alkaloid (+)-crispine A via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step.

  我们报告了一种新颖，简便，不对称的方法，通过高度非对映选择性的N-酰基环化反应作为关键的合成步骤来合成抗肿瘤生物碱（+）- crispineA。
• Diastereoselective Intramolecular α-Amidoalkylation Reactions of <scp>l</scp>-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinolines
  作者：Eva García、Sonia Arrasate、Esther Lete、Nuria Sotomayor

  DOI：10.1021/jo051584w

  日期：2005.12.1

  Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).