(R)-(+)-N-(1-phenyl-2-hydroxyethyl)succinimide | 241466-60-4

• 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: (R)-(+)-N-(1-phenyl-2-hydroxyethyl)succinimide
• 英文别名: (R)-N-(2-hydroxy-1-phenylethyl)succinimide；N-(2-hydroxy-1(R)-phenylethyl)-succinimide；1-[(1R)-2-hydroxy-1-phenylethyl]pyrrolidine-2,5-dione
• CAS: 241466-60-4
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: ZLINDUHWXXJDAX-JTQLQIEISA-N

物化性质

• 沸点：
  461.1±38.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-N-(1-phenyl-2-hydroxyethyl)succinimide 在 magnesium 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3R,7aS)-3-phenyl-7a-(2-phenylethyl)-2,3,7,7a-tetrahydropyrrolo[2,1-b]oxazol-5-one
  参考文献：
  名称：

  Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 1: N-Acyliminium ion cyclisations with an internal arene nucleophile

  摘要：

  A series of chiral non-racemic 5,5- and 5,6-bicyclic lactams is prepared from (R)-phenylglycinol. These are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3:1 diastereoselectivity. From four structures determined by X-ray crystallography, it follows that spiro indenes are formed preferentially with retention of configuration at the spiro carbon atom and spiro naphthalenes with inversion. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.128
• 作为产物：
  描述：

  丁二酸酐 、 D-苯甘氨醇 在 三乙胺 作用下， 以 甲苯 为溶剂， 以59%的产率得到(R)-(+)-N-(1-phenyl-2-hydroxyethyl)succinimide
  参考文献：
  名称：

  Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 1: N-Acyliminium ion cyclisations with an internal arene nucleophile

  摘要：

  A series of chiral non-racemic 5,5- and 5,6-bicyclic lactams is prepared from (R)-phenylglycinol. These are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3:1 diastereoselectivity. From four structures determined by X-ray crystallography, it follows that spiro indenes are formed preferentially with retention of configuration at the spiro carbon atom and spiro naphthalenes with inversion. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.128

文献信息

• Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 2: N-Acyliminium ion cyclisations with an internal alkene nucleophile
  作者：Abood A Bahajaj、John M Vernon、Giles D Wilson

  DOI：10.1016/j.tet.2003.10.127

  日期：2004.1

  Chiral non-racemic bicyclic and tricyclic oxylactams obtained in two steps from N-(2-hydroxy-1(R)-phenylethyl)-succinimide and phthalimide are cyclised diastereoselectively in formic acid to give spiro[cyclohexane-1,2′-pyrrolidin]-5-ones and spiro[cyclohexane-1,1′-isoindolin]-3-ones, respectively.

  由N-（2-羟基-1（R）-苯乙基）-琥珀酰亚胺和邻苯二甲酰亚胺分两步获得的手性非外消旋双环和三环氧基内酰胺在甲酸中非对映选择性环化，生成螺[环己烷-1,2'-吡咯烷丁]分别为-5-个和螺[环己烷-1,1'-异吲哚啉] -3-个。
• An asymmetric synthesis of the key precursor to (−)-indolizomycin
  作者：Michael D. Groaning、A.I. Meyers

  DOI：10.1016/s0040-4039(99)00728-5

  日期：1999.6

  Using chiral bicyclic lactams, containing an alpha,beta-unsaturation, the key precursor of (-)-indolizomycin was obtained in optically pure form. The sequence involved a >20:1 diastereoselective cyclopropanation of the unsaturated lactam 5 employing sulfoxonium methylide. TiCl4 mediated addition of allyltrimethylsilane afforded pyrrolidone 7 in a diastereomeric ratio of >20:1. The appropriately substituted pyrrolidone 2 was prepared by debenzylation and subsequent alkylation with 3-bromoproponic ester. The six step sequence from commercially available starting materials was performed in 26% overall yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Expedient syntheses of indolizidines (−)-167B and (−)-209D
  作者：Guncheol Kim、Eun-ju Lee

  DOI：10.1016/s0957-4166(01)00369-x

  日期：2001.8

  Indolizidine alkaloids (+/-)-167B and (-)-209D were synthesized via an expedient route using hydroacylation and amination. (C) 2001 Published by Elsevier Science Ltd.
• Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 1: N-Acyliminium ion cyclisations with an internal arene nucleophile
  作者：Abood A Bahajaj、Madeleine H Moore、John M Vernon

  DOI：10.1016/j.tet.2003.10.128

  日期：2004.1

  A series of chiral non-racemic 5,5- and 5,6-bicyclic lactams is prepared from (R)-phenylglycinol. These are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3:1 diastereoselectivity. From four structures determined by X-ray crystallography, it follows that spiro indenes are formed preferentially with retention of configuration at the spiro carbon atom and spiro naphthalenes with inversion. (C) 2003 Elsevier Ltd. All rights reserved.