2-(2-hydroxy-1(R)-phenylethyl)-3(R)-hydroxy-3-(3-phenylpropyl)-2,3-dihydroisoindol-1(1H)-one | 675589-46-5

• 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-(2-hydroxy-1(R)-phenylethyl)-3(R)-hydroxy-3-(3-phenylpropyl)-2,3-dihydroisoindol-1(1H)-one
• 英文别名: (3R)-3-hydroxy-2-[(1R)-2-hydroxy-1-phenylethyl]-3-(3-phenylpropyl)isoindol-1-one
• CAS: 675589-46-5
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: RQGZMKQFXPEXBP-UKILVPOCSA-N

物化性质

• 沸点：
  617.2±55.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxy-1(R)-phenylethyl)-3(R)-hydroxy-3-(3-phenylpropyl)-2,3-dihydroisoindol-1(1H)-one 在 三氯化铝 、 三氟乙酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 (R,R)-2'-(2-hydroxy-1-phenylethyl)-1,2,3,4,2',3'-hexahydrospiro[naphthalene-1,1'-isoindol]-3'-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：

  3-phenylpropyl-magnesium bromide 、 (R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione 以 四氢呋喃 为溶剂， 以65%的产率得到2-(2-hydroxy-1(R)-phenylethyl)-3(R)-hydroxy-3-(3-phenylpropyl)-2,3-dihydroisoindol-1(1H)-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, 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.