(S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide | 862819-80-5

• 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: (S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide
• 英文别名: N-[(2S)-1-[tert-butyl(diphenyl)silyl]oxy-3-(3,4-dimethoxyphenyl)propan-2-yl]-4-oxopentanamide
• CAS: 862819-80-5
• 化学式: C₃₂H₄₁NO₅Si
• 分子量: 547.767
• InChiKey: WZGZUJAOFBVBDX-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以36%的产率得到(5S,10bS)-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：

  Enantioselective synthesis of pyrrolo[2,1-a]isoquinolones via stereocontrolled N-acyliminium ion cyclisations

  摘要：

  Stereocontrolled N-acyliminium ion cyclisation of L-DOPA derived succinimide 5 has been investigated. Addition of organolithiums to chiral non-racemic 5 yields oxoamides, which are cyclised diastereoselectively upon treatment with BF3-OEt2, to afford 5,10b-trans pyrroloisoquinolones in moderate yields and high ee (99%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02319-4
• 作为产物：
  描述：

  N-Boc-3,4-二甲氧基-L-苯丙氨酸 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 (S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide
  参考文献：
  名称：

  Enantioselective synthesis of pyrrolo[2,1-a]isoquinolones via stereocontrolled N-acyliminium ion cyclisations

  摘要：

  Stereocontrolled N-acyliminium ion cyclisation of L-DOPA derived succinimide 5 has been investigated. Addition of organolithiums to chiral non-racemic 5 yields oxoamides, which are cyclised diastereoselectively upon treatment with BF3-OEt2, to afford 5,10b-trans pyrroloisoquinolones in moderate yields and high ee (99%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02319-4

文献信息

• 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%).