N-cyclohexylidene-2-methyl-1-propanamine | 25115-59-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-cyclohexylidene-2-methyl-1-propanamine
• 英文别名: N-isobutyliminocyclohexane；N-cyclohexylidene-2-methylpropan-1-amine；Cyclohexyliden-isobutyl-amin；N-Cyclohexyliden-isobutylamin；cyclohexylidene-isobutyl-amine；N-(2-methylpropyl)cyclohexanimine
• CAS: 25115-59-7
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: GSEJNBQMFWBHNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-cyclohexylidene-2-methyl-1-propanamine 在 过氧乙酸 作用下， 生成 2-isobutyl-1,2-oxazaspiro<2,5>octane
  参考文献：
  名称：

  Krimm, Chemische Berichte, 1958, vol. 91, p. 1057,1066

  摘要：

  DOI：
• 作为产物：
  描述：

  异丁胺 、 环己酮 以 二氯甲烷 为溶剂， 生成 N-cyclohexylidene-2-methyl-1-propanamine
  参考文献：
  名称：

  不寻常的反应性环状酸酐扩大了卡斯塔格诺利-库什曼反应的范围

  摘要：

  在Castagnoli-Cushman与亚胺的反应中合成和测试各种“含唑”环酸酐的过程中，已发现了一种具有显着活性的吡咯型酸酐。它显示出与N-烷基和N-芳基亚胺，特别是与“可烯醇化”的α-CH亚胺的高效反应，后者通常无法与大多数已知的环状酸酐反应。该酸酐的反应性已经通过其烯醇形式的有效共振稳定来证明。这一发现扩大了现有的高反应性环状酸酐库，并进一步证实了酸酐烯化对于有效的Castagnoli-Cushman反应的重要性。

  DOI：

  10.1021/acs.joc.8b02164

文献信息

• Synthesis of functionalised cyclopentanes by intramolecular radical-mediated cyclisations of terminal allenic ketones
  作者：Gerald Pattenden、Graeme M. Robertson

  DOI：10.1016/s0040-4020(01)97179-0

  日期：1985.1

  Electrolysis of a series of terminal allenic ketones e.g. (7), (10), (17) and (21) is shown to result in intramolecular reductive cyclisation, through the -mode, producing five-membered rings, (8), (9), (20) and (22) respectively, incorporating a bridgehead hydroxyl group. The unsaturated alcohols (8), (20) and (22), are also obtained when the allenic ketones (7), (17) and (21) are treated with sodium

  一系列末端烯丙基酮如（7），（10），（17）和（21）的电解显示通过-模式导致分子内还原环化，产生五元环（8），（9） ），（20）和（22）分别掺入桥头羟基。当用萘二甲酸钠处理烯丙基酮（7），（17）和（21）时，也获得不饱和醇（8），（20）和（22）。相反，通过在-模式下环化，在萘钠中的（10）处理产生低产率（7％）的异构体茚满醇（11）。
• Synthesis of spiroisoindolinones by palladium-catalyzed heterocyclization of 2-iodobenzoyl chloride with ketimines
  作者：Chan Sik Cho、Xue Wu、Li Hong Jiang、Sang Chul Shim、Hong Rak Kim

  DOI：10.1002/jhet.5570360147

  日期：1999.1

  2-Iodobenzoyl chloride reacts with ketimines in acetonitrile at 100° under carbon monoxide pressure in the presence of a catalytic amount of a palladium catalyst together with triethylamine to afford the corresponding spiroisoindolinones in high yields.

  2-碘苯甲酰氯在催化量的钯催化剂和三乙胺的存在下，在一氧化碳压力下于100°C下与乙酮中的酮亚胺反应，以高收率得到相应的螺异吲哚满酮。
• The Castagnoli–Cushman reaction of bicyclic pyrrole dicarboxylic anhydrides bearing electron-withdrawing substituents
  作者：Maria E. Chizhova、Dmitry V. Dar’in、Mikhail Krasavin

  DOI：10.1016/j.mencom.2020.07.030

  日期：2020.7

  Four anhydrides of 1-(carboxymethyl)pyrrole-2-carboxylic acids bearing electron-withdrawing substituents at positions 6 or 7 of the bicyclic system have been investigated in the Castagnoli–Cushman reaction with imines. 6-Benzoyl- and 7-sulfamoyl-substituted anhydrides demonstrated lower reactivity while 7-benzoyl derivative displayed broader substrate scope. These findings have been rationalized from

  在Castagnoli-Cushman与亚胺的反应中，已经研究了在双环系统的6或7位带有吸电子取代基的1-（羧甲基）吡咯-2-羧酸的四种酸酐。6-苯甲酰基-和7-氨磺酰基取代的酸酐显示出较低的反应性，而7-苯甲酰基衍生物显示出较宽的底物范围。这些发现已从机制的角度进行了合理化。
• Formation of 1,2,3,4-tetrahydro-2-pyridones by aza-annulation of imines with acrylate derivatives
  作者：K. Paulvannan、John R. Stille

  DOI：10.1021/jo00046a011

  日期：1992.9

  The aza-annulation of imines with activated acrylate derivatives was studied as a means of preparing the corresponding 1,2,3,4-tetrahydro-2-pyridones. Through the use of reagents known to facilitate the formation of amide bonds from carboxylic acids, several methods of activating the acrylate species were compared. The acrylate derivatives studied were acryloyl chloride and acrylic anhydride as well as acrylic acid activated by reaction with EtO2CCl, (PhO)2P(O)N3, or MCPI. Optimum annulation was obtained with imines derived from cyclohexanone to produce octahydro-2-quinolone products. The N-isobutylimine prepared from cyclopentanone also produced selective ring annulation to efficiently produce the corresponding bicyclic product, but the reaction with the imine of n-butanal produced lower yields of cyclic product. Ring formation was relatively unaffected by substituents at the a-position of the acrylate derivative, demonstrated by the use of methacrylate, but beta-substituents hindered the annulation process and, in turn, increased the amounts of byproduct resulting from only N-acylation of the imine. Increasing the steric bulk of the imine alkyl substituent produced the opposite effect; the relative amount of N-acylation compared to complete aza-annulation was diminished as the size of the substituent was increased. Mechanistic features of the reaction are discussed in terms of product distribution and competition experiments.
• The Preparation and Properties of Oxaziranes
  作者：William D. Emmons

  DOI：10.1021/ja01578a043

  日期：1957.11