(3-methyl-2,5-dihydro-1H-pyrrol-1-yl)(phenyl)methanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-methyl-2,5-dihydro-1H-pyrrol-1-yl)(phenyl)methanone
• 英文别名: (3-methyl-2H-pyrrol-1(5H)-yl)(phenyl)methanone；(3-Methyl-2,5-dihydropyrrol-1-yl)-phenylmethanone
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: YPVKFLICXAQNRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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-丙-2-烯基苯甲酰胺 在 Grubbs catalyst first generation 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 (3-methyl-2,5-dihydro-1H-pyrrol-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes

  摘要：

  Ruthenium alkylidene 1 and molybdenum alkylidene 2 have been utilized in the ring-closing metathesis (RCM) of dienes containing gem-disubstituted olefins to yield td-and tetrasubstituted cyclic olefins. Dienes with sterically demanding and/or electron-withdrawing substituents such as Ph, CO2Me, and Bu-t were cyclized successfully with 2, but did not cyclize with 1. Tetrasubstituted cyclic olefins could be formed with 2, but not using alkylidene-1. Dienes with allylic functional groups yielded functionalized cyclic olefins when treated with 1.

  DOI：

  10.1021/jo970877p

文献信息

• A Unique Ruthenium Carbyne Complex: A Highly Thermo-endurable Catalyst for Olefin Metathesis
  作者：Mingbo Shao、Lu Zheng、Weixia Qiao、Jingjing Wang、Jianhui Wang

  DOI：10.1002/adsc.201200119

  日期：2012.10.8

  A cationic ruthenium carbyne complex was prepared and was found to initiate olefin metathesis reactions with good activities, which throws a new light on the design of a new type of ruthenium catalyst for RCM reactions. More importantly, no double bond isomerized by-product was observed even at elevated temperatures in reactions catalyzed by the new carbyne complex. A mechanism involving the in situ

  制备了一种阳离子钌卡宾络合物，发现该催化剂能引发烯烃复分解反应，并具有良好的活性，这为新型的用于RCM反应的钌催化剂的设计提供了新的思路。更重要的是，即使在新的卡宾络合物催化的反应中，即使在升高的温度下，也没有观察到双键异构化的副产物。还提出了一种机制，该机制涉及通过将碘化物添加到卡宾碳上而将卡宾碳烯原位转化为钌卡宾络合物。
• PQS-2: ring-closing- and cross-metathesis reactions on lipophilic substrates; in water only at room temperature, with in-flask catalyst recycling
  作者：Bruce H. Lipshutz、Subir Ghorai

  DOI：10.1016/j.tet.2009.11.010

  日期：2010.1

  (PQS-2) of the recently introduced PQS is described. It forms catalytic nanomicellar reactors in water that provide the medium for highly reactive Ru carbene catalysts to effect both ring closing metathesis to trisubstituted olefins and cross-metathesis reactions at room temperature. The catalyst can be recycled without removal from the reaction vessel.

  描述了最近引入的PQS的泛醇侧链氢化形式（PQS-2）。它在水中形成催化纳米胶束反应器，为高反应性Ru卡宾催化剂提供了介质，以实现三环烯烃的闭环易位和室温下的交叉复分解反应。催化剂可以再循环而无需从反应容器中移出。
• Synthesis and reactivity of oxygen chelated ruthenium carbene metathesis catalysts
  作者：Yiran Zhang、Mingbo Shao、Huizhu Zhang、Yuqing Li、Dongyu Liu、Yu Cheng、Guiyan Liu、Jianhui Wang

  DOI：10.1016/j.jorganchem.2014.01.017

  日期：2014.4

  and the terminal oxygen of the benzylidene ether are both coordinated to the metal to give an octahedral structure. However, the carbonyl oxygen of complexes (H2IMes)(Cl)2RuC(H)[(C6H3X)OCH(CH2C(O)OCH2)(X = H, OMe)] does not coordinate to the metal due to the steric effect of the lactone. All these complexes were used as catalysts for olefin metathesis reactions and all exhibited excellent performances

  Hoveyda催化剂的引发速率受作用于Ru O配位的电子和空间效应的影响。为了提高Hoveyda催化剂的活性，已经开发了一系列新型的含有N-杂环卡宾（NHC）和羰基的氧螯合钌卡宾复分解催化剂，并研究了它们对烯烃复分解反应的催化活性。配合物的脂肪族端基（H 2 IMes）（Cl）2 Ru C（H）[（C 6 H 3 X）OCH（Me）（C（O）OEt）（X = H，OMe，Me，NO 2）]通过连接直链酯进行官能化。复杂（H 2 IMes）（Cl）2的X射线结构Ru C（H）[（C 6 H 4）OCH（Me）（C（O）NMe 2）]显示酰胺的羰基氧和亚苄基醚的末端氧均与金属配位，得到八面体结构。但是，配合物（H 2 IMes）（Cl）2 Ru C（H）[（C 6 H 3 X）OCH（CH 2 C（O）OCH 2）（X = H，OMe）]由于内酯的空间效应不与金属配位。所有这些络合物均用作烯烃
• Ferrocene Redox Controlled Reversible Immobilization of Ruthenium Carbene in Ionic Liquid: A Versatile Catalyst for Ring-Closing Metathesis
  作者：Guiyan Liu、Haiyan He、Jianhui Wang

  DOI：10.1002/adsc.200800713

  日期：2009.7

  A ferrocene‐tagged ruthenium carbene 15 that can be reversibly immobilized in an ionic liquid (IL) via the controlled oxidation and reduction of a ferrocene tag was prepared. This offers a new strategy which uses redox chemistry to control immobilization and to recycle both the catalyst and the IL. In this experiment, 11 recycles were performed for the ring‐closing metathesis (RCM) of a substrate using

  制备了二茂铁标记的钌卡宾15，它可以通过二茂铁标签的受控氧化和还原反应可逆地固定在离子液体（IL）中。这提供了一种新策略，该策略使用氧化还原化学来控制固定化并循环使用催化剂和IL。在该实验中，使用16种底物进行了11次循环进行底物的闭环复分解（RCM）。作为离子液体（IL）中的催化剂。更重要的是，反应完成后，仅通过添加十甲基二茂铁（DMFc）还原阳离子二茂铁，然后用苯萃取，即可轻松地将钌催化剂与负载型IL分离。因此，该再循环系统提供了一种简单的方法来再循环钌催化剂和IL。
• Recycling a Homogeneous Catalyst through a Light-Controlled Phase Tag
  作者：Guiyan Liu、Jianhui Wang

  DOI：10.1002/anie.200906034

  日期：2010.6.14

  A homogeneous ruthenium–carbene complex was tagged with a light‐responding nitrobenzospiropyran group to control its solubility through reversible conversion between its neutral (lipophilic) and ionic (lipophobic) states using light irradiation (see scheme; Mes=mesityl). This tagged complex has significant catalytic activity in ring‐closing metathesis reactions and was recycled several times.

  均匀的钌-卡宾络合物带有一个光响应性硝基苯并螺吡喃基团，以通过使用光辐照在其中性（亲脂性）和离子性（疏脂性）状态之间可逆转换来控制其溶解度（参见方案； Mes = mesityl）。这种标记的复合物在闭环复分解反应中具有显着的催化活性，并被回收了数次。