(3R,7aS)-3-phenyl-7a-(3-phenylpropyl)-2,3,7,7a-tetrahydropyrrolo[2,1-b]oxazol-5-one | 675589-41-0

• 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: (3R,7aS)-3-phenyl-7a-(3-phenylpropyl)-2,3,7,7a-tetrahydropyrrolo[2,1-b]oxazol-5-one
• 英文别名: (3R,7aS)-3-phenyl-7a-(3-phenylpropyl)-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• CAS: 675589-41-0
• 化学式: C₂₁H₂₃NO₂
• 分子量: 321.419
• InChiKey: HMGYZFUEKRYSSN-FPOVZHCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,7aS)-3-phenyl-7a-(3-phenylpropyl)-2,3,7,7a-tetrahydropyrrolo[2,1-b]oxazol-5-one 在 三氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (R,R)-1'-(2-hydroxy-1-phenylethyl)-1,2,3,4-tetrahydrospiro[naphthalene-1,2'-pyrrolidin]-5'-one 、 1'-(2-hydroxy-1-phenylethyl)-1,2,3,4-tetrahydrospiro[naphthalene-1,2'-pyrrolidin]-5'-one
  参考文献：
  名称：

  Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones

  摘要：

  双环内酰胺14-17在三氯化铝处理下于1,2-二氯乙烷中进行异构化，以高产率（>3:1）的非对映选择性生成螺内酰胺；由X射线晶体学确定的结构19a和22b可知，优先形成的是在螺碳原子上保持构型的茚19和21，以及构型翻转的萘20和22。

  DOI：

  10.1039/c39940002511
• 作为产物：
  描述：

  3-phenylpropyl-magnesium bromide 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 (3R,7aS)-3-phenyl-7a-(3-phenylpropyl)-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

文献信息

• Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones
  作者：Abood A. Bahajaj、Patrick D. Bailey、Madeleine H. Moore、Keith M. Morgan、John M. Vernon

  DOI：10.1039/c39940002511

  日期：——

  Bicyclic lactams 14–17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.

  双环内酰胺14-17在三氯化铝处理下于1,2-二氯乙烷中进行异构化，以高产率（>3:1）的非对映选择性生成螺内酰胺；由X射线晶体学确定的结构19a和22b可知，优先形成的是在螺碳原子上保持构型的茚19和21，以及构型翻转的萘20和22。
• 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.