2-(3,4-Epoxycyclohexyl)ethylamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 2-(3,4-Epoxycyclohexyl)ethylamine
• 英文别名: 8-hydroxy-2-azabicyclo[3.3.1]nonane；2-(7-Oxabicyclo[4.1.0]heptan-3-yl)ethanamine
• 化学式: C₈H₁₅NO
• mdl: MFCD19212376
• 分子量: 141.213
• InChiKey: CEGMGIGLDSXBRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3,4-Epoxycyclohexyl)ethylamine 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-(tert-butoxycarbonyl)-8-oxo-2-azabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Model Studies on the Synthesis of Madangamine Alkaloids. Assembly of the Macrocyclic Rings

  摘要：

  Using simplified model derivatives, the assembly of the macrocyclic rings of madangamines, including the 13- and 14-membered D rings of madangamlnes C-E, the all-cis-triunsaturated 15-membered D ring of madangamine A, and the (Z,Z)-unsaturated 11-membered E ring common to madangamines A-E, has been studied.

  DOI：

  10.1021/ol301672y
• 作为产物：
  描述：

  4-乙烯基-1-环己烯 在 sodium tetrahydroborate 、 sodium azide 、 2-甲基-2-丁烯 、 三氟化硼乙醚 、 水 、 三乙胺 、 间氯过氧苯甲酸 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(3,4-Epoxycyclohexyl)ethylamine
  参考文献：
  名称：

  Model Studies on the Synthesis of Madangamine Alkaloids. Assembly of the Macrocyclic Rings

  摘要：

  Using simplified model derivatives, the assembly of the macrocyclic rings of madangamines, including the 13- and 14-membered D rings of madangamlnes C-E, the all-cis-triunsaturated 15-membered D ring of madangamine A, and the (Z,Z)-unsaturated 11-membered E ring common to madangamines A-E, has been studied.

  DOI：

  10.1021/ol301672y

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.
• US8916329B2
  申请人：——

  公开号：US8916329B2

  公开（公告）日：2014-12-23
• Model Studies on the Synthesis of Madangamine Alkaloids. Assembly of the Macrocyclic Rings
  作者：Stefano Proto、Mercedes Amat、Maria Pérez、Roberto Ballette、Federica Romagnoli、Andrea Mancinelli、Joan Bosch

  DOI：10.1021/ol301672y

  日期：2012.8.3

  Using simplified model derivatives, the assembly of the macrocyclic rings of madangamines, including the 13- and 14-membered D rings of madangamlnes C-E, the all-cis-triunsaturated 15-membered D ring of madangamine A, and the (Z,Z)-unsaturated 11-membered E ring common to madangamines A-E, has been studied.