2-(2-methylenecyclohexyl)ethanamine | 217633-08-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(2-methylenecyclohexyl)ethanamine
• 英文别名: 2-(2-Methylidenecyclohexyl)ethanamine
• CAS: 217633-08-4
• 化学式: C₉H₁₇N
• mdl: MFCD19205672
• 分子量: 139.241
• InChiKey: KPWXOEVLIDBVCR-UHFFFAOYSA-N

物化性质

• 沸点：
  203.8±9.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 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：

  2-(2-methylenecyclohexyl)ethanamine 在 2 作用下， 反应 336.0h， 以90%的产率得到cis-7a-methyloctahydroindole
  参考文献：
  名称：

  Catalytic Intramolecular Hydroamination of Hindered Alkenes Using Organolanthanide Complexes

  摘要：

  The intramolecular hydroamination of hindered alkenes has been developed as a versatile route to heterocyclic systems. The current process utilizes the unhindered catalyst system [Cp(2)(TMS)LnMe](2) (Ln = Sm, Nd) to effect the cyclization of hindered amino olefins, providing products containing quaternary centers. The process tolerates a wide variety of substitution patterns, allowing the construction of monocyclic as well as fused and bridged bicyclic heterocycles. Two experimental procedures were employed in this study: one without solvent, minimizing waste streams, the other in deuterated solvents, allowing NMR monitoring of the reaction. The yield of each reaction was high, with NMR analysis of the reactions in progress showing clean conversion from starting material to a single product in most cases.

  DOI：

  10.1021/jo981345r
• 作为产物：
  描述：

  2-[2-(2-methylidenecyclohexyl)ethyl]isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-(2-methylenecyclohexyl)ethanamine
  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

• Reaction Control in Synthetic Organic Photochemistry: Switching between [5+2] and [2+2] Modes of Cycloaddition
  作者：Claudio Roscini、Kara L. Cubbage、Malcolm Berry、Andrew J. Orr-Ewing、Kevin I. Booker-Milburn

  DOI：10.1002/anie.200904059

  日期：2009.11.2

  Split personality: Reaction conditions that enable powerful control over the mode of photocycloaddition in maleimides have been developed. Direct irradiation favors the [5+2] mode whereas sensitized irradiation allows a complete switch to the [2+2] mode (see scheme; TBS=tert‐butyldimethylsilyl).

  人格分裂：已开发出能够有效控制马来酰亚胺中光环加成模式的反应条件。直接辐射有利于[5 + 2]模式，而敏化辐射则允许完全切换到[2 + 2]模式（请参阅方案； TBS =叔丁基二甲基甲硅烷基）。
• 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。
• Catalytic Intramolecular Hydroamination of Hindered Alkenes Using Organolanthanide Complexes
  作者：Gary A. Molander、Eric D. Dowdy

  DOI：10.1021/jo981345r

  日期：1998.11.1

  The intramolecular hydroamination of hindered alkenes has been developed as a versatile route to heterocyclic systems. The current process utilizes the unhindered catalyst system [Cp(2)(TMS)LnMe](2) (Ln = Sm, Nd) to effect the cyclization of hindered amino olefins, providing products containing quaternary centers. The process tolerates a wide variety of substitution patterns, allowing the construction of monocyclic as well as fused and bridged bicyclic heterocycles. Two experimental procedures were employed in this study: one without solvent, minimizing waste streams, the other in deuterated solvents, allowing NMR monitoring of the reaction. The yield of each reaction was high, with NMR analysis of the reactions in progress showing clean conversion from starting material to a single product in most cases.