N-(cyclohex-2-en-1-yl)-N-methylamine | 86766-74-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(cyclohex-2-en-1-yl)-N-methylamine
• 英文别名: N-cyclohex-2-enyl-N-methyl-amine；N-methylcyclohex-2-en-1-amine；N-methylcyclohex-2-enamine；3-Methylamino-cyclohexen
• CAS: 86766-74-7
• 化学式: C₇H₁₃N
• 分子量: 111.187
• InChiKey: QKQONPQFTLIOJU-UHFFFAOYSA-N

物化性质

• 沸点：
  97 °C(Press: 135 Torr)
• 密度：
  0.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-(cyclohex-2-en-1-yl)-N-methylamine 在 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 N-(2-cyclohexen-1-yl)-2-iodo-N-methylacetamide
  参考文献：
  名称：

  Atom-transfer annulations in heterocycle synthesis. An efficient synthesis of (-)-trachelanthamidine and related ring systems

  摘要：

  DOI：

  10.1021/ja00230a044
• 作为产物：
  描述：

  2-环己烯醇 在 18-冠醚-6 sodium hydroxide 、 sodium hydride 作用下， 以 乙醇 、 xylene 为溶剂， 反应 42.75h， 生成 N-(cyclohex-2-en-1-yl)-N-methylamine
  参考文献：
  名称：

  Effects of temperature on atom transfer cyclization reactions of allylic .alpha.-iodo esters and amides

  摘要：

  Atom-transfer cyclizations of allyl iodoacetates and N-allyl-N-methyliodoacetamides are much more efficient at 80-degrees-C than at 25-degrees-C. At 80-degrees-C, beta-(iodomethyl) lactones and lactams are formed rapidly and in good yield under standard atom-transfer conditions (sunlamp irradiation of iodide and 10% hexabutylditin in benzene for 10-60 min). It is proposed that this temperature effect is responsible for some unusual observations by Jolly and Livinghouse in the cyclization of N-cyclohexenyl-N-methyliodoacetamide. The results suggest that the beneficial effect of temperature arises because an increase in the rate of rotation of the OC-O or OC-N bond in the intermediate radicals begins to convert syn radicals (which cannot cyclize) to anti radicals (which can cyclize). Consistent with this hypothesis, the radical derived from N,N-diallyliodoacetamide (which always has a favorable arrangement for cyclization) closes with excellent efficiency at 25-degrees-C.

  DOI：

  10.1021/jo00008a032

文献信息

• (2-hydroxy)ethyl-thioureas useful as modulators of alpha2B adrenergic receptors
  申请人：ALLERGAN SALES, INC.

  公开号：US20020161051A1

  公开（公告）日：2002-10-31

  Compounds of formula (i) and of formula (ii) 1 wherein the symbols have the meaning disclosed in the specification, specifically or selectively modulate &agr; 2B and/or &agr; 2C adrenergic receptors in preference over &agr; 2A adrenergic receptors, and as such are useful for alleviating chronic pain and allodynia and have no or only minimal cardivascular and/or sedatory activity.

  式（i）和式（ii）的化合物 其中符号的含义在说明书中披露，特别或选择性地调节&agr; 2B 和/或&agr; 2C 肾上腺素受体，优先于&agr; 2A 肾上腺素受体，因此对缓解慢性疼痛和触痛有用，并且几乎没有或只有极小的心血管和/或镇静活性。
• Synthesis of α-Chlorolactams by Cyanoborohydride-Mediated Radical Cyclization of Trichloroacetamides
  作者：Guilhem Coussanes、Harald Jakobi、Stephen Lindell、Josep Bonjoch

  DOI：10.1002/chem.201800210

  日期：2018.6.7

  A cyanoborohydride‐promoted radical cyclization methodology has been developed to access α‐chlorolactams in a simple and efficient way using NaBH3CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of α‐chlorolactams (mono‐ and bicyclic), which were tested for herbicidal activity, trans‐3‐chloro‐4‐methyl‐1‐(

  已开发出一种氰基硼氢化物促进的自由基环化方法，可使用NaBH 3 CN和三氯乙酰胺（可从烯丙基和均烯丙基仲胺中轻松获得）以简单有效的方式获得α-氯内酰胺。这种方法学允许合成α-氯内酰胺（单环和双环）文库，并对其除草活性进行了测试，反式-3-氯-4-甲基-1-（3-三氟甲基）苯基-2-吡咯烷酮是最活跃。
• 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。
• Direct Comparison of C–H Bond Amination Efficacy through Manipulation of Nitrogen-Valence Centered Redox: Imido versus Iminyl
  作者：Matthew J. T. Wilding、Diana A. Iovan、Alexandra T. Wrobel、James T. Lukens、Samantha N. MacMillan、Kyle M. Lancaster、Theodore A. Betley

  DOI：10.1021/jacs.7b08714

  日期：2017.10.18

  magnetometry, single crystal X-ray diffraction, XAS, and EXAFS for 6. The high-spin (S = 5/2) imidos exhibit characteristically short Fe–N bonds (3: 1.708(4) Å; 5: 1.674(11) Å), whereas the corresponding iminyls exhibit elongated Fe–N bonds (2: 1.768(2) Å; 6: 1.761(6) Å). Comparison of the pre-edge absorption feature (1s → 3d) in the X-ray absorption spectra reveals that the four imido/iminyl complexes

  的还原先前报道的亚氨基自由基（氩L）的FeCl（• Ñ（C 6 H ^ 4 - p -吨丁基））（2）与氢石墨提供的相应的高自旋（小号= 5 / 2）亚氨基（氩L） Fe（N（C 6 H 4 - p - t Bu））（3）（Ar L = 5-甲磺酰基-1,9- （2,4,6-Ph 3 C 6 H 2）双吡啶。三配位亚氨基（Ar L）Fe（NAd）的氧化（5）与氯三苯甲烷反应制得（Ar L）FeCl（• NAd）（6），并伴随排出Ph 3 C（C 6 H 5）CPh 2。相应的芳基/烷基酰亚胺/亚氨基双（3，2 ; 5，6）的特点是EPR，零场57的Fe穆斯堡尔，磁力测定，单晶X射线衍射，XAS和用于EXAFS 6。的高自旋（小号= 5 / 2）显示出imidos特征短的Fe-N键（3：1.708（4）; 5：1.674（11）Å），而相应的亚氨基表现出拉长的Fe–N键（2：1.768（2）Å;
• Synthesis of 1-Arylcycloalkenamines by Intramolecular Arylation of Lithiated Ureas
  作者：Michael B. Tait、Philipp A. Ottersbach、Daniel J. Tetlow、Jonathan Clayden

  DOI：10.1021/op500173q

  日期：2014.10.17

  deprotonation of N′-arylurea derivatives of cyclohexenamines by alkyllithiums leads to migration of the N′-aryl substituent from N′ to the allylic position α to N via rearrangement of a urea-stabilised allyllithium intermediate. The product ureas may be solvolysed to reveal 1-arylcyclohexenamines.

  的去质子化Ñ 'cyclohexenamines的-arylurea衍生物通过烷基锂通向迁移Ñ ' -芳基取代基从N'经由脲稳定化的烯丙基锂中间体的重排的烯丙基位置α到N。产物脲可以被溶剂分解以显示1-芳基环己胺。