cis-3-Hexeneamine | 136294-40-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cis-3-Hexeneamine
• 英文别名: 1-amino-3-(Z)-hexene；(Z)-hex-3-en-1-amine
• CAS: 136294-40-1
• 化学式: C₆H₁₃N
• 分子量: 99.1759
• InChiKey: VGZNFMCCYIOLAF-ARJAWSKDSA-N

物化性质

• 沸点：
  129.8±19.0 °C(Predicted)
• 密度：
  0.794±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-3-Hexeneamine 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 39.0h， 生成 acetoxyacetic acid methyl ester
  参考文献：
  名称：

  Tin tetrachloride-induced π-cyclizations of glycine cation equivalents to substituted pipecolic acid derivatives

  摘要：

  Cationic pi-cyclization reactions of N-(3-alkenyl)-N-(methoxycarbonyl)acetoxyglycine esters induced by tin tetrachloride in dichloromethane are described. Reactions started and quenched with water at -78-degrees-C mainly yield cis-4-hydroxypipecolic esters, whereas reactions quenched after warm-up to room temperature provide trans-4-chloropipecolic esters as major products. A mechanistic scheme is advanced which adequately explains these results. The essentials are a rapid cationic aza-Cope equilibrium of the incipient iminium cation, and participation of the ester moiety through formation of a relatively stable bicyclic dioxycarbenium cation as pivotal intermediate.

  DOI：

  10.1016/s0040-4020(01)86443-7
• 作为产物：
  描述：

  (Z)-2-(hex-3-en-1-yl)isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 cis-3-Hexeneamine
  参考文献：
  名称：

  通过温度调节镍催化的可切换位点选择性烯烃加氢烷基化**

  摘要：

  开发了一种镍催化的可切换位点选择性烯烃加氢烷基化反应。反应温度的选择导致提供从单一烯烃底物开始的区域发散性氢化烷基化产物的方案。

  DOI：

  10.1002/anie.202205537

文献信息

• Organic Dye Photocatalyzed Synthesis of Functionalized Lactones and Lactams via a Cyclization–Alkynylation Cascade
  作者：Diana Cavalli、Jerome Waser

  DOI：10.1021/acs.orglett.4c01078

  日期：2024.5.24

  accessible homoallylic cesium oxalates using ethynylbenziodoxolone (EBX) reagents has been developed. The reaction gave access to valuable functionalized lactones and lactams in up to 88% yield via the formation of two new C–C bonds. The transformation was carried out on primary, secondary, and tertiary homoallylic alcohols and primary homoallylic amines and could be applied to the synthesis of spirocyclic

  开发了一种使用乙炔基苯并氧酮 (EBX) 试剂对易于获得的同烯丙基草酸铯进行有机染料光催化内酯化-炔基化反应。该反应通过形成两个新的 C-C 键，获得了有价值的官能化内酯和内酰胺，产率高达 88%。该转化针对伯、仲、叔高烯丙醇和伯高烯丙胺进行，可应用于螺环化合物以及稠合和桥联双环内酯的合成。
• 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.