1-acetyl-3-methyl-4-methylene-pyrrolidine | 60205-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-acetyl-3-methyl-4-methylene-pyrrolidine
• 英文别名: 1-(3-Methyl-4-methylidenepyrrolidin-1-yl)ethanone
• CAS: 60205-25-6
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: CZPLRAUEOHQBRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N,N-diallylacetamide 在 [Ru(cod)Cl₂]_n 作用下， 以 异丙醇 为溶剂， 反应 0.25h， 生成 1-acetyl-3-methyl-4-methylene-pyrrolidine
  参考文献：
  名称：

  Ruthenium(ii)-catalysed cycloisomerisation of 1,6-dienes by focused microwave dielectric heating: improved rates and selectivities leading to exo-methylenecyclopentanes

  摘要：

  我们在此报告了微波介电加热在钌催化的1,6-二烯环异构化中的影响。对于一系列1,6-二烯底物，反应速度显著提高，并且异构体纯度与传统热加热相当或更高。

  DOI：

  10.1039/b513798e

文献信息

• Ruthenium(II)-Catalyzed Isomer-Selective Cyclization of 1,6-Dienes Leading to <i>e</i><i>xo</i>-Methylenecyclopentanes:  Unprecedented Cycloisomerization Mechanism Involving Ruthenacyclopentane(hydrido) Intermediate
  作者：Yoshihiko Yamamoto、Yu-ichiro Nakagai、Naoki Ohkoshi、Kenji Itoh

  DOI：10.1021/ja010134s

  日期：2001.7.1

  In the presence of a catalytic amount of ruthenium(II) complexes, [RuCl2(cod)](n), RuCl2(cod)(MeCN)(2), [RuCl2(nbd)](n). [RuCl2(CO)(3)](2), and Cp*Ru(cod)Cl, 1,6-dienes were effectively converted into the corresponding exo-methylenecyclopentanes in good to excellent yields with good isomer purity in i-PrOH at 90 degreesC. The alcoholic solvent was essential for the present catalytic cyclization, and the efficiency increased in the following order: t-BuOH << EtOH less than or equal to i-PrOH. In contrast, a Ru(0) complex. (C6Me6)Ru(cod), catalyzed the cycloisomerization only in 1,2-dichloroethane. The unusual isomer-selectivity occurred when a 1,7-octadiene was subjected to cyclization to give a similar exo-methylenecyclopentane isomer as the major product. The identical isomer selectivity was observed for the cyclization of unsymmetrical 1,6-dienes having one terminal- and one internal-alkene termini. On the basis of the results from the studies using the known ruthenium hydrides and deuterium-labeling substrates, the novel mechanism via the Ru(II) <--> Ru(IV) system involving a ruthenacyclopentane(hydrido) intermediate was proposed, which better explains the particular regiochemistry of the present cyclization than other previous mechanisms.
• Ruthenium-Catalyzed Highly Efficient Intramolecular Olefin Coupling of α,ω-Dienes. Facile and Regioselective Synthesis of <i>exo</i>-Methylenecyclopentanes
  作者：Yoshihiko Yamamoto、Naoki Ohkoshi、Mitsutosi Kameda、Kenji Itoh

  DOI：10.1021/jo982467m

  日期：1999.4.1
• SCHMITZ E.; HEUCK U.; HABISCH D., J. PRAKT. CHEM. <JPCE-AO>, 1976, 318, NO 3, 471-478
  作者：SCHMITZ E.、 HEUCK U.、 HABISCH D.

  DOI：——

  日期：——
• Ruthenium(ii)-catalysed cycloisomerisation of 1,6-dienes by focused microwave dielectric heating: improved rates and selectivities leading to exo-methylenecyclopentanes
  作者：Ian J. S. Fairlamb、Gerard P. McGlacken、Felix Weissberger

  DOI：10.1039/b513798e

  日期：——

  We herein report the effect of microwave dielectric heating in the Ru-catalysed cycloisomerisation of 1,6-dienes. Substantially improved reaction rates are attained for a series of 1,6-diene substrates, with equivalent or higher isomeric purity than conventional thermal heating.

  我们在此报告了微波介电加热在钌催化的1,6-二烯环异构化中的影响。对于一系列1,6-二烯底物，反应速度显著提高，并且异构体纯度与传统热加热相当或更高。