N-(2,2-diphenylpent-4-enyl)-4-methylbenzamide | 1011527-36-8

• 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: N-(2,2-diphenylpent-4-enyl)-4-methylbenzamide
• CAS: 1011527-36-8
• 化学式: C₂₅H₂₅NO
• 分子量: 355.48
• InChiKey: JYCGNSXPNRKCGV-UHFFFAOYSA-N

物化性质

• 沸点：
  547.1±50.0 °C(predicted)
• 密度：
  1.071±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2,2-diphenylpent-4-enyl)-4-methylbenzamide 在 双(乙腈)氯化钯(II) 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以93%的产率得到[2-(Chloromethyl)-4,4-diphenylpyrrolidin-1-yl]-(4-methylphenyl)methanone
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular Chloroamination of Alkenes

  摘要：

  A mild and facile Pd-catalyzed intramolecular chloroamination of unactivated alkenes has been described. This reaction takes place at room temperature and is tolerant of synthetically useful acid-sensitive functional groups. Generally high exo-selectivities are observed in the formation of a variety of 5- and 6-membered rings. This system is unique in its ability to tolerate multidentate ligands on palladium, which opens up the possibility of controlling the absolute sense of induction using a chiral ligand.

  DOI：

  10.1021/ol702922c
• 作为产物：
  描述：

  2,2-diphenyl-4-pentenylamine 、 对甲基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以1.6714 g的产率得到N-(2,2-diphenylpent-4-enyl)-4-methylbenzamide
  参考文献：
  名称：

  Palladium-Catalyzed Intramolecular Chloroamination of Alkenes

  摘要：

  A mild and facile Pd-catalyzed intramolecular chloroamination of unactivated alkenes has been described. This reaction takes place at room temperature and is tolerant of synthetically useful acid-sensitive functional groups. Generally high exo-selectivities are observed in the formation of a variety of 5- and 6-membered rings. This system is unique in its ability to tolerate multidentate ligands on palladium, which opens up the possibility of controlling the absolute sense of induction using a chiral ligand.

  DOI：

  10.1021/ol702922c

文献信息

• Palladium-Catalyzed Carboamination of Alkenes Promoted by <i>N-</i>Fluorobenzenesulfonimide via C−H Activation of Arenes
  作者：Carolyn F. Rosewall、Paul A. Sibbald、Dmitry V. Liskin、Forrest E. Michael

  DOI：10.1021/ja9031659

  日期：2009.7.15

  unactivated nucleophilic arenes are incorporated to give carboamination products in good yields. A variety of protected amide and carbamate groups are tolerated, and various five-, six-, and seven-membered rings are formed in good yields. Under these conditions, halobenzenes are activated at the C-H bond rather than the C-X bond, and very high regioselectivity for the para substitution product is observed

  该报告描述了一种独特的 Pd 催化的受保护氨基烯烃的氧化碳胺化，其中加入了廉价的未活化的亲核芳烃，从而以良好的产率得到碳胺化产物。可以耐受各种受保护的酰胺和氨基甲酸酯基团，并以良好的产率形成各种五元、六元和七元环。在这些条件下，卤代苯在 CH 键而不是 CX 键处被活化，并且在所有情况下都观察到对位取代产物的非常高的区域选择性。我们建议这种碳胺化是通过 Pd(IV) 烷基中间体的亲电芳香取代发生的。
• FeBr3-catalyzed regioselective intramolecular sulfenoamination of unactivated terminal olefins
  作者：Lin-Chuang Zheng、Lin Li、Lili Duan、Yue-Ming Li

  DOI：10.1016/j.tet.2019.130619

  日期：2019.11

  A method for regioselective intramolecular sulfenoamination of unactivated terminal olefins was reported. Using sulfonyl hydrazides as the sulfur sources, FeBr3 as the catalyst and (NH4)2S2O8 as the oxidant, different sulfenylmethylpyrrolidines and sulfenylmethylpiperidines were obtained in moderate to high yields via intramolecular sulfenoamination of (sulfon)amidopentenes or (sulfon)amidohexenes

  报道了未活化的末端烯烃的区域选择性分子内磺酰胺化的方法。以磺酰肼为硫源，以FeBr 3为催化剂，以（NH 4）2 S 2 O 8为氧化剂，通过（磺）酰胺基戊二烯或（磺）的分子内磺酰胺化反应，以中等至高收率获得了不同的亚磺酰基甲基吡咯烷和亚磺酰基甲基哌啶。氨基己烯。
• Chelation-Driven Rearrangement of Primary Alkyl Aminopalladation Products to Stable Trisubstituted Alkyl-Palladium Complexes
  作者：Carolyn F. Rosewall、Erica L. Ingalls、Werner Kaminsky、Forrest E. Michael

  DOI：10.1002/anie.201412033

  日期：2015.4.7

  this study, a set of equilibrating alkyl–palladium complexes were subtly tuned to form either a primary or trisubstituted alkyl complex as the more thermodynamically favored state, depending on either the substrate or reaction conditions. An X‐ray crystal structure of the trisubstituted alkyl–palladium complex is presented and compared with the corresponding primary alkyl complex. The mechanism for

  使用催化形成高度取代的碳中心是人们一直追求的目标，但是高度取代的碳原子与过渡金属的配合物很少，而且影响差异程度较大的碳原子与配合物的相对稳定性的因素了解甚少。在这项研究中，根据底物或反应条件，微调了一组平衡的烷基-钯配合物以形成伯或三取代的烷基配合物，成为更热力学上有利的状态。给出了三取代烷基钯配合物的X射线晶体结构，并将其与相应的伯烷基配合物进行了比较。讨论了重新排列的机制以及驱动稳定性变化的因素。
• Palladium-Catalyzed Diamination of Unactivated Alkenes Using <i>N</i>-Fluorobenzenesulfonimide as Source of Electrophilic Nitrogen
  作者：Paul A. Sibbald、Forrest E. Michael

  DOI：10.1021/ol9000087

  日期：2009.3.5

  A remarkable Pd-catalyzed diamination of unactivated alkenes using N-fluorobenzenesulfonimide (NFBS) as an aminating reagent is described. The reaction occurs in an intra/intermolecular fashion, incorporating one nitrogen donor from the substrate and the other from the NFBS, thereby generating cyclic diamine derivatives in a single step. The products are differentially protected at both nitrogens,

  描述了使用N-氟苯磺酰亚胺（NFBS）作为胺化试剂的Pd催化的未活化烯烃的重整。该反应以分子内/分子间方式发生，从底物引入一个氮供体，从NFBS引入另一个氮供体，从而在一个步骤中生成环状二胺衍生物。产品在两个氮原子上都得到了不同的保护，从而实现了最大的合成灵活性。Pd（IV）物种的中间性被认为是造成NFBS异常反应的原因。
• Enantioselective Palladium-Catalyzed Diamination of Alkenes Using <i>N</i>-Fluorobenzenesulfonimide
  作者：Erica L. Ingalls、Paul A. Sibbald、Werner Kaminsky、Forrest E. Michael

  DOI：10.1021/ja4043406

  日期：2013.6.19

  An enantioselective Pd-catalyzed vicinal diamination of unactivated alkenes using N-fluorobenzenesulfonimide as both an oxidant and a source of nitrogen is reported. The use of Ph-pybox and Ph-quinox ligands afforded differentially protected vicinal diamines in good yields with high enantioselectivities. Mechanistic experiments revealed that the high enantioselectivity arises from selective formation

  报道了使用 N-氟苯磺酰亚胺作为氧化剂和氮源对未活化烯烃进行对映选择性 Pd 催化的邻位二胺化。Ph-pybox 和 Ph-quinox 配体的使用以良好的收率和高对映选择性提供了差异保护的邻二胺。机理实验表明，高对映选择性仅源于手性 Pd 配合物的四种可能的非对映异构氨基钯化产物中的一种的选择性形成。氨基钯络合物通过 X 射线晶体学表征。