N-[(cyclohex-3-en-1-yl)methyl]prop-2-en-1-amine | 165335-05-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[(cyclohex-3-en-1-yl)methyl]prop-2-en-1-amine
• 英文别名: N-(3-Cyclohexenylmethyl)allylamine；N-(cyclohex-3-en-1-ylmethyl)prop-2-en-1-amine
• CAS: 165335-05-7
• 化学式: C₁₀H₁₇N
• mdl: MFCD11157166
• 分子量: 151.252
• InChiKey: DXOFAUGBAFPKRA-UHFFFAOYSA-N

物化性质

• 沸点：
  214.7±9.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯苯磺酸 、 N-[(cyclohex-3-en-1-yl)methyl]prop-2-en-1-amine 以 乙醚 为溶剂， 生成 N-(3-Cyclohexenylmethyl)allylammonium p-chlorobenzenesulfonate
  参考文献：
  名称：

  Epoxidation of Primary and Secondary Alkenylammonium Salts with Dimethyldioxirane, Methyl(trifluoromethyl)dioxirane, and m-Chloroperbenzoic Acid. A General Synthetic Route to Epoxyalkylamines

  摘要：

  Selective syn-epoxidation of C=C double bonds in primary and secondary alkenylammonium arenesulfonate salts 3H(+), to give the corresponding epoxyalkylammonium salts 4H(+), has been achieved by reaction with electrophilic O-transfer reagents such as m-CPBA, methyl(trifluoromethyl)dioxirane (TFDO), and dimethyldioxirane (DMDO). Epoxyalkylamines 4 are easily obtained in high yields from the corresponding epoxyalkylammonium salts 4H(+) by simple deprotonation with sodium carbonate. The ammonium group deactivates the C=C double bond, and hence the epoxidation rate is slower than in the case of simple olefins. II-Bonding interaction between the ammonium group and the O-transfer reagent(m-CPBA and DMDO) in the transition state is claimed to account for the rate enhancement and diastereoselectivity observed when the necessary conformational requirements are established. The allylic ammonium group is shown to be very efficient in directing the epoxidation with m-CPBA and DMDO on the syn-diastereoface.

  DOI：

  10.1021/jo00117a020
• 作为产物：
  描述：

  3-环己烯甲醛 在 sodium tetrahydroborate 、 magnesium sulfate 、 magnesium 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 78.0h， 生成 N-[(cyclohex-3-en-1-yl)methyl]prop-2-en-1-amine
  参考文献：
  名称：

  Electron transfer induced ring opening of 2-(bromomethyl)aziridines by magnesium in methanol

  摘要：

  Magnesium metal in methanol was used as a simple electron transfer induced ring-opening reagent of 2-(bromomethyl)aziridines to afford allylamines derivatives in 70-90% yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00728-7

文献信息

• Epoxidation of Primary and Secondary Alkenylammonium Salts with Dimethyldioxirane, Methyl(trifluoromethyl)dioxirane, and m-Chloroperbenzoic Acid. A General Synthetic Route to Epoxyalkylamines
  作者：Gregorio Asensio、Rossella Mello、Carmen Boix-Bernardini、Maria Elena Gonzalez-Nunez、Gloria Castellano

  DOI：10.1021/jo00117a020

  日期：1995.6

  Selective syn-epoxidation of C=C double bonds in primary and secondary alkenylammonium arenesulfonate salts 3H(+), to give the corresponding epoxyalkylammonium salts 4H(+), has been achieved by reaction with electrophilic O-transfer reagents such as m-CPBA, methyl(trifluoromethyl)dioxirane (TFDO), and dimethyldioxirane (DMDO). Epoxyalkylamines 4 are easily obtained in high yields from the corresponding epoxyalkylammonium salts 4H(+) by simple deprotonation with sodium carbonate. The ammonium group deactivates the C=C double bond, and hence the epoxidation rate is slower than in the case of simple olefins. II-Bonding interaction between the ammonium group and the O-transfer reagent(m-CPBA and DMDO) in the transition state is claimed to account for the rate enhancement and diastereoselectivity observed when the necessary conformational requirements are established. The allylic ammonium group is shown to be very efficient in directing the epoxidation with m-CPBA and DMDO on the syn-diastereoface.
• Electron transfer induced ring opening of 2-(bromomethyl)aziridines by magnesium in methanol
  作者：Kourosch Abbaspour Tehrani、Tuyen NguyenVan、Michinori Karikomi、Mario Rottiers、Norbert De Kimpe

  DOI：10.1016/s0040-4020(02)00728-7

  日期：2002.8

  Magnesium metal in methanol was used as a simple electron transfer induced ring-opening reagent of 2-(bromomethyl)aziridines to afford allylamines derivatives in 70-90% yield. (C) 2002 Elsevier Science Ltd. All rights reserved.