N-methyl-N-(3-methyl-2-buten-1-yl)amine | 29151-30-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-N-(3-methyl-2-buten-1-yl)amine
• 英文别名: N,3-dimethylbut-2-en-1-amine；N-methyl-N-prenylamine；N,3-Dimethylbut-2-enylamin
• CAS: 29151-30-2
• 化学式: C₆H₁₃N
• mdl: MFCD19159698
• 分子量: 99.1759
• InChiKey: ZZPSWDZXWOPXGB-UHFFFAOYSA-N

物化性质

• 沸点：
  113.2±9.0 °C(Predicted)
• 密度：
  0.763±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 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：

  N-methyl-N-(3-methyl-2-buten-1-yl)amine 以14%的产率得到
  参考文献：
  名称：

  GRIGORYAN D. V.; GEVORKYAN A. ZH.; CHERKEZYAN A. A.; BABAYAN A. T., AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1981, 34, HO 5, 417-421

  摘要：

  DOI：
• 作为产物：
  描述：

  在 氢氧化钾 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N-methyl-N-(3-methyl-2-buten-1-yl)amine
  参考文献：
  名称：

  Highly Enantioselective Intramolecular Cyclopropanation Reactions of N-Allylic-N-methyldiazoacetamides Catalyzed by Chiral Dirhodium(II) Carboxamidates

  摘要：

  Catalytic diazo decomposition of representative N-allylic-N-methyldiazoacetamides produced the corresponding intramolecular cyclopropanation products in good to excellent yields and with exceptional enantiocontrol. In the simplest case, with N-allyl-N-methyldiazoacetamide, catalysis by dirhodium(II) tetrakis[methyl 2-oxapyrrolidine-5(S)-carboxylate], Rh-2(5(S)-MEPY)(4), achieved the highest yield and enantioselectivity (93% eel. Dirhodium(II) tetrakis[methyl 2-oxo-1-(3-phenylpropanoyl)imidazolidin-4(S)-carboxylate] Rh-2(4S)-MPPIM)(4), was preferred for substituted N-allylic-N-methyldiazoacetamides from which 92-95% ee's were obtained in intramolecular cyclopropanation reactions (88-95% yields), even when the catalyst was employed in only 0.1 mol %, Competition with intramolecular dipolar cycloaddition was minimized with the use of N-methyldiazoacetamides relative to N-tert-butyldiazoacetamides.

  DOI：

  10.1021/jo9519219

文献信息

• Synthesis of the Azepinoindole Framework via Oxidative Heck (Fujiwara-Moritani) Cyclization
  作者：Erik Van der Eycken、Pavel Donets

  DOI：10.1055/s-0030-1260057

  日期：2011.7

  A catalytic oxidative Heck (Fujiwara-Moritani) cyclization has been evaluated for construction of the azepinoindole framework starting from readily available 3-indoleacetic acid amides. The supporting role of the amide group in the substrate has been demonstrated necessary for the success of the cyclization.

  已评估了一种催化氧化赫克（Fujiwara-Moritani）环化反应，用于从易得的3-吲哚乙酸酰胺构建吖啶吲哚骨架。结果表明，在底物中酰胺基团的支持作用对于环化反应的成功至关重要。
• Synthesis of Symmetric 1,4-Diamino-2-Butynes via a Cu(I)-Catalyzed One-Pot A³-Coupling/Decarboxylative Coupling of a Propiolic Acid, an Aldehyde, and an Amine
  作者：Huangdi Feng、Denis S. Ermolat’ev、Gonghua Song、Erik V. Van der Eycken

  DOI：10.1021/jo300562j

  日期：2012.6.1

  A novel microwave-assisted approach for the one-pot Cu(I)-catalyzed A3-coupling/decarboxylative coupling (PA2-coupling) of a propiolic acid, an aldehyde, and an amine, resulting in the formation of diversely substituted 1,4-diamino-2-butynes,is described. It is noteworthy that this new multicomponent coupling provides an efficient access to introduce alkyl and aryl group at the 1,4-position of the

  一种新颖的微波辅助方法，用于一锅铜（一）催化丙酸，醛和胺的A 3偶联/脱羧偶联（PA 2偶联），从而形成不同取代的1描述了4-4-二氨基-2-丁炔。值得注意的是，这种新的多组分偶联提供了在1，4-二氨基-2-丁炔的1，4-位上引入烷基和芳基的有效途径。
• Catalytic Alkene Carboaminations Enabled by Oxidative Proton-Coupled Electron Transfer
  作者：Gilbert J. Choi、Robert R. Knowles

  DOI：10.1021/jacs.5b05377

  日期：2015.7.29

  N-arylamides (bond dissociation free energies ∼ 100 kcal/mol) via concerted proton-coupled electron transfer (PCET) and mediating efficient carboamination reactions of the resulting amidyl radicals. This manner of PCET activation, which finds its basis in numerous biological redox processes, enables the formal homolysis of a stronger amide N-H bond in the presence of weaker allylic C-H bonds, a selectivity that

  在这里，我们描述了一种由铱光催化剂和弱磷酸盐碱组成的双催化剂体系，该体系能够通过协同质子耦合电子转移（PCET）选择性地均化 N-芳基酰胺的 NH 键（键解离自由能 ~ 100 kcal/mol） ) 并介导所得酰胺基自由基的有效碳胺化反应。这种 PCET 活化方式在众多生物氧化还原过程中找到了基础，它能够在较弱的烯丙基 CH 键存在下对较强的酰胺 NH 键进行形式均裂，这种选择性在常规分子 H 原子受体中并不常见。此外，这种转化可以从简单的酰胺原料中获得广泛的结构复杂的杂环。设计，合成范围，
• Aryne-Mediated [2,3]-Sigmatropic Rearrangement of Tertiary Allylic Amines
  作者：Juan Zhang、Zhi-Xiong Chen、Ting Du、Bing Li、Yonghong Gu、Shi-Kai Tian

  DOI：10.1021/acs.orglett.6b02344

  日期：2016.10.7

  3]-sigmatropic rearrangement of quaternary allylic ammonium ylides via in situ activation of tertiary allylic amines with arynes under mild conditions. Using 2-(trimethylsilyl)aryl triflates as aryne precursors, a range of tertiary allylic amines bearing electron-withdrawing groups underwent [2,3]-sigmatropic rearrangement to furnish structurally diverse homoallylic amines in moderate to good yields. The reaction

  已经建立了通过在温和条件下用芳烃原位活化叔烯丙基胺来[4,3]-σ重排季铵烯丙基铵的新策略。使用2-（三甲基甲硅烷基）芳基三氟甲磺酸酯作为芳烃前体，对一系列带有吸电子基团的叔烯丙基胺进行[2,3]-σ重排，以中等至良好的收率提供结构多样的均胺。该反应能够构建具有出色对映体纯度的四级立体中心和具有极高非对映选择性的官能化环丙烷。
• Too Short-Lived or Not Existing Species:<i>N</i>-Azidoamines Reinvestigated
  作者：Klaus Banert、Tom Pester

  DOI：10.1021/acs.joc.9b00034

  日期：2019.4.5

  Treatment of N-chlorodimethylamine with sodium azide in dichloromethane does not lead to N-azidodimethylamine, as thought for more than 50 years. Instead, surprisingly, (azidomethyl)dimethylamine is generated with good reproducibility. A plausible reaction mechanism to explain the formation of this product is presented. The reaction of lithium dibenzylhydrazide with tosyl azide does not result in the

  如50多年来所认为的那样，用叠氮化钠在二氯甲烷中处理N-氯二甲基胺不会导致N-叠氮基二甲基胺。相反，令人惊讶地，产生了具有良好再现性的（叠氮甲基）二甲基胺。提出了一个合理的反应机理来解释该产物的形成。如前所述，二苄基肼基锂与甲苯磺酰基叠氮化物的反应不会导致生成N-叠氮基胺，可以通过IR光谱法在环境温度下对其进行检测。重氮基转移至酰肼锂的其他实验表明，中间体N-叠氮基胺的寿命很短，或者通过同步断裂两个N-N键直接生成1,1-二氮烯来绕开它们的形成。