N-1-(1-cyclohexenyl)ethylphthalimide | 325490-27-5

• 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: N-1-(1-cyclohexenyl)ethylphthalimide
• 英文别名: 2-[1-(Cyclohexen-1-yl)ethyl]isoindole-1,3-dione；2-[1-(cyclohexen-1-yl)ethyl]isoindole-1,3-dione
• CAS: 325490-27-5
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: JDAKFCPIWCEPLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-1-(1-cyclohexenyl)ethylphthalimide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以96.7%的产率得到1-(cyclohex-1-en-1-yl)ethan-1-amine
  参考文献：
  名称：

  Resolution of β-unsaturated amines with isopropylidene glycerol hydrogen phthalate

  摘要：

  1-Phenyl-2-propenylamine 2, 1-phenyl-2-propinylamine 3, 1-(1-cyclohexenyl)ethylamine 4, (E)-2-ethylidenecyclohexylamine 5 and alpha -methylallylamine hydrochloride 6 were selected as candidates for resolution with isopropylidene glycerol hydrogen phthalate 1, previously described as an efficient resolving agent of 1-arylalkylamines. With only the exception of 5, all these substrates were resolved by (S)-1. In particular both the enantiomers of 2 and 3 were obtained in excellent yields and with very high enantiomeric excesses. The absolute configurations of non-racemic forms of 2, 3 and 4, not prepared before except those of 3, were established by correlation with the respective hydrogenation products. The enantiomeric excesses of all the resolved substrates were accurately determined by chiral HPLC analysis. The fact that 1 resolves 4 and 6 but not their saturated analogues and shows higher efficiency in resolving 2 and 3 than 1-phenylpropylamine indicates the positive influence of the presence of beta -unsaturation on the resolvability of aminic substrates with such an acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00373-6
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 1-环己烯-1-甲醇,a-甲基- 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以39.2%的产率得到N-1-(1-cyclohexenyl)ethylphthalimide
  参考文献：
  名称：

  Resolution of β-unsaturated amines with isopropylidene glycerol hydrogen phthalate

  摘要：

  1-Phenyl-2-propenylamine 2, 1-phenyl-2-propinylamine 3, 1-(1-cyclohexenyl)ethylamine 4, (E)-2-ethylidenecyclohexylamine 5 and alpha -methylallylamine hydrochloride 6 were selected as candidates for resolution with isopropylidene glycerol hydrogen phthalate 1, previously described as an efficient resolving agent of 1-arylalkylamines. With only the exception of 5, all these substrates were resolved by (S)-1. In particular both the enantiomers of 2 and 3 were obtained in excellent yields and with very high enantiomeric excesses. The absolute configurations of non-racemic forms of 2, 3 and 4, not prepared before except those of 3, were established by correlation with the respective hydrogenation products. The enantiomeric excesses of all the resolved substrates were accurately determined by chiral HPLC analysis. The fact that 1 resolves 4 and 6 but not their saturated analogues and shows higher efficiency in resolving 2 and 3 than 1-phenylpropylamine indicates the positive influence of the presence of beta -unsaturation on the resolvability of aminic substrates with such an acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00373-6

文献信息

• Resolution of β-unsaturated amines with isopropylidene glycerol hydrogen phthalate
  作者：Marco Pallavicini、Ermanno Valoti、Luigi Villa、Oreste Piccolo

  DOI：10.1016/s0957-4166(00)00373-6

  日期：2000.10

  1-Phenyl-2-propenylamine 2, 1-phenyl-2-propinylamine 3, 1-(1-cyclohexenyl)ethylamine 4, (E)-2-ethylidenecyclohexylamine 5 and alpha -methylallylamine hydrochloride 6 were selected as candidates for resolution with isopropylidene glycerol hydrogen phthalate 1, previously described as an efficient resolving agent of 1-arylalkylamines. With only the exception of 5, all these substrates were resolved by (S)-1. In particular both the enantiomers of 2 and 3 were obtained in excellent yields and with very high enantiomeric excesses. The absolute configurations of non-racemic forms of 2, 3 and 4, not prepared before except those of 3, were established by correlation with the respective hydrogenation products. The enantiomeric excesses of all the resolved substrates were accurately determined by chiral HPLC analysis. The fact that 1 resolves 4 and 6 but not their saturated analogues and shows higher efficiency in resolving 2 and 3 than 1-phenylpropylamine indicates the positive influence of the presence of beta -unsaturation on the resolvability of aminic substrates with such an acid. (C) 2000 Elsevier Science Ltd. All rights reserved.