(Z)-4-hexenylamine | 120788-32-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z)-4-hexenylamine
• 英文别名: (Z)-hex-4-en-1-amine
• CAS: 120788-32-1
• 化学式: C₆H₁₃N
• 分子量: 99.1759
• InChiKey: AZJUGPLDDAZZTB-IHWYPQMZSA-N

物化性质

• 沸点：
  126.4±9.0 °C(Predicted)
• 密度：
  0.794±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：

  (Z)-4-hexenylamine 在 碘 、 chloroamine-T 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 17.0h， 生成 2-(1-iodoethyl)-1-[(4-methylphenyl)sulfonyl]pyrrolidine
  参考文献：
  名称：

  Electrophilic cyclization of N-alkenylamides using a chloramine-T/I2 system

  摘要：

  A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three- to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the chloramine-T/I-2 system functions as an effective iodonium species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.003
• 作为产物：
  描述：

  (Z)-2-(hex-4-en-1-yl)isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (Z)-4-hexenylamine
  参考文献：
  名称：

  钯催化N-保护的己-4-烯胺和1-，3-和4-取代的戊-4-烯胺的碳氨化的温和条件。吡咯烷形成的范围，局限性和机理。

  摘要：

  在N保护的γ-氨基烯烃与芳基溴化物的Pd催化碳氨化反应中使用弱碱Cs2CO3会导致官能团和烯烃取代的耐受性大大提高。衍生自（E）-或（Z）-己-4-烯基胺的底物被立体定向​​转化为2,1'-二取代的吡咯烷产物，该产物是通过在烯烃上表面氮原子和芳基的表面加成而产生的。以高收率进行4-取代的戊-4-烯胺衍生物的转化，得到2,2-二取代的产物，并且以高收率产生顺式-2,5-或反式-2,3-二取代的吡咯烷，并具有优异的非对映选择性。 -在C1或C3处带有取代基的被保护的戊-4-烯基胺。反应可耐受各种官能团，包括酯，硝基，和烯醇化的酮 详细说明了这些转换的范围和局限性，以及解释了所观察到的产物立体化学的模型。另外，还讨论了氘标记实验，该实验表明这些反应通过中间钯（芳基）（酰胺）配合物的顺氨基钯催化进行，而与烯烃的取代程度或反应条件无关。

  DOI：

  10.1021/jo801631v

文献信息

• Tietze, Lutz F.; Bratz, Matthias; Pretor, Martina, Chemische Berichte, 1989, vol. 122, p. 1955 - 1962
  作者：Tietze, Lutz F.、Bratz, Matthias、Pretor, Martina

  DOI：——

  日期：——
• Correlation between Functionality Preference of Ru Carbenes and <i>exo</i>/<i>endo</i> Product Selectivity for Clarifying the Mechanism of Ring-Closing Enyne Metathesis
  作者：Ok Suk Lee、Kyung Hwan Kim、Jinwoo Kim、Kuktae Kwon、Taedong Ok、Hyotcherl Ihee、Hee-Yoon Lee、Jeong-Hun Sohn

  DOI：10.1021/jo401420f

  日期：2013.9.6

  Functionality preferences of metathesis Ru carbenes to various alkenes and alkynes with electronic and steric diversity were determined by using time-dependent fluorescence quenching. The functionality preferences depend not only on the properties of multiple bonds but also on the ligands on Ru. There was a good correlation between functionality preference and the metathesis reaction outcome. The correlation between functionality preference and exo/endo product ratio offers a solution to resolve the mechanistic issue related with alkene- vs alkyne-initiated pathway in ring-closing enyne metathesis. The correlation indicates the preference is likely to dictate the reaction pathway and eventually the outcome of the reaction. The Ru catalyst favoring alkyne over alkene provides more endo product, indicating that the reaction mainly initiates at the alkyne. By changing the substitution pattern, the preference can be reversed to give an exclusive exo product.
• Mild Conditions for Pd-Catalyzed Carboamination of <i>N</i>-Protected Hex-4-enylamines and 1-, 3-, and 4-Substituted Pent-4-enylamines. Scope, Limitations, and Mechanism of Pyrrolidine Formation
  作者：Myra Beaudoin Bertrand、Joshua D. Neukom、John P. Wolfe

  DOI：10.1021/jo801631v

  日期：2008.11.21

  with aryl bromides leads to greatly increased tolerance of functional groups and alkene substitution. Substrates derived from (E)- or (Z)-hex-4-enylamines are stereospecifically converted to 2,1'-disubstituted pyrrolidine products that result from suprafacial addition of the nitrogen atom and the aryl group across the alkene. Transformations of 4-substituted pent-4-enylamine derivatives proceed in high

  在N保护的γ-氨基烯烃与芳基溴化物的Pd催化碳氨化反应中使用弱碱Cs2CO3会导致官能团和烯烃取代的耐受性大大提高。衍生自（E）-或（Z）-己-4-烯基胺的底物被立体定向​​转化为2,1'-二取代的吡咯烷产物，该产物是通过在烯烃上表面氮原子和芳基的表面加成而产生的。以高收率进行4-取代的戊-4-烯胺衍生物的转化，得到2,2-二取代的产物，并且以高收率产生顺式-2,5-或反式-2,3-二取代的吡咯烷，并具有优异的非对映选择性。 -在C1或C3处带有取代基的被保护的戊-4-烯基胺。反应可耐受各种官能团，包括酯，硝基，和烯醇化的酮 详细说明了这些转换的范围和局限性，以及解释了所观察到的产物立体化学的模型。另外，还讨论了氘标记实验，该实验表明这些反应通过中间钯（芳基）（酰胺）配合物的顺氨基钯催化进行，而与烯烃的取代程度或反应条件无关。
• Electrophilic cyclization of N-alkenylamides using a chloramine-T/I2 system
  作者：Yoshinobu Morino、Ikumasa Hidaka、Yoji Oderaotoshi、Mitsuo Komatsu、Satoshi Minakata

  DOI：10.1016/j.tet.2006.10.003

  日期：2006.12

  A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three- to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the chloramine-T/I-2 system functions as an effective iodonium species. (c) 2006 Elsevier Ltd. All rights reserved.