2-[(Z)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-[(2S)-2-tri(propan-2-yl)silyloxypropylidene]amino]ethenyl]isoindole-1,3-dione | 236114-51-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[(Z)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-[(2S)-2-tri(propan-2-yl)silyloxypropylidene]amino]ethenyl]isoindole-1,3-dione
• CAS: 236114-51-5
• 化学式: C₂₈H₄₆N₂O₄Si₂
• 分子量: 530.855
• InChiKey: YKLWHTZZAXFJLH-YGVDEJEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.75
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  68.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(Z)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-[(2S)-2-tri(propan-2-yl)silyloxypropylidene]amino]ethenyl]isoindole-1,3-dione 在 盐酸 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-[(R)-4-Amino-5-((S)-1-hydroxy-ethyl)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl]-isoindole-1,3-dione; hydrochloride
  参考文献：
  名称：

  Stereoselective synthesis of chiral 3,4,5-trisubstituted 1,5-dihydropyrrol-2-ones from azadienes

  摘要：

  A new access to enantiopure 3-phthalimido-4-amino-5-(1-hydroxyalkyl) 1,5-dihydropyrrol-2-ones has been developed from 1,3-azadienes. Stereoselective Lewis acid catalyzed addition of a cyano group to an azadiene, followed by intramolecular ring closure, in a four-step one-pot synthesis, results in the formation of gamma-lactams in satisfactory yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00130-5
• 作为产物：
  描述：

  (2S)-2-(triisopropylsilyloxy)propionaldehyde 在 正丁基锂 、 三乙胺 作用下， 以 正己烷 、 正庚烷 为溶剂， 反应 3.0h， 生成 2-[(Z)-2-[tert-butyl(dimethyl)silyl]oxy-2-[(E)-[(2S)-2-tri(propan-2-yl)silyloxypropylidene]amino]ethenyl]isoindole-1,3-dione
  参考文献：
  名称：

  Stereoselective synthesis of chiral 3,4,5-trisubstituted 1,5-dihydropyrrol-2-ones from azadienes

  摘要：

  A new access to enantiopure 3-phthalimido-4-amino-5-(1-hydroxyalkyl) 1,5-dihydropyrrol-2-ones has been developed from 1,3-azadienes. Stereoselective Lewis acid catalyzed addition of a cyano group to an azadiene, followed by intramolecular ring closure, in a four-step one-pot synthesis, results in the formation of gamma-lactams in satisfactory yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00130-5

文献信息

• Microwave-assisted solvent-free organic reactions: Synthesis of β-lactams from 1,3-azadienes
  作者：Giorgio Martelli、Giuseppe Spunta、Mauro Panunzio

  DOI：10.1016/s0040-4039(98)01302-1

  日期：1998.8

  Ring-closure of 1,3-azadienes to beta-lactam rings is efficiently and quickly carried out under solvent-free conditions in an open-vessel microwave system. The synthesis of N-tert-butyldimethylsilyl azetidinones is reported. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Stereoselective synthesis of chiral 3,4,5-trisubstituted 1,5-dihydropyrrol-2-ones from azadienes
  作者：Elisa Bandini、Giorgio Martelli、Giuseppe Spunta、Alessandro Bongini、Mauro Panunzio、Giovanni Piersanti

  DOI：10.1016/s0957-4166(99)00130-5

  日期：1999.4

  A new access to enantiopure 3-phthalimido-4-amino-5-(1-hydroxyalkyl) 1,5-dihydropyrrol-2-ones has been developed from 1,3-azadienes. Stereoselective Lewis acid catalyzed addition of a cyano group to an azadiene, followed by intramolecular ring closure, in a four-step one-pot synthesis, results in the formation of gamma-lactams in satisfactory yields. (C) 1999 Elsevier Science Ltd. All rights reserved.