N-(2-bromo-2-propen-1-yl)-N-(2-propen-1-yl)acetamide | 87280-23-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-bromo-2-propen-1-yl)-N-(2-propen-1-yl)acetamide
• 英文别名: N-acetyl-N-allyl(2-bromoallyl)amine；N-allyl-N-(2-bromoallyl)acetamide；N-(2-bromoprop-2-enyl)-N-prop-2-enylacetamide
• CAS: 87280-23-7
• 化学式: C₈H₁₂BrNO
• 分子量: 218.093
• InChiKey: PWSOKCHKDPRJCW-UHFFFAOYSA-N

物化性质

• 沸点：
  105-108 °C(Press: 1.5 Torr)
• 密度：
  1.297±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-bromo-2-propen-1-yl)-N-(2-propen-1-yl)acetamide 在 Pd(PPh₃)(OAc)2 N-苯基马来酰亚胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 2.6h， 生成 (3aR,8aS)-6-Acetyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-pyrrolo[3,4-f]isoindole-1,3-dione
  参考文献：
  名称：

  The regioselectivity of rhodium and palladium-catalysed cyclisations of 2-bromo-1,6- and -1,7-dienes

  摘要：

  DOI：

  10.1016/s0040-4020(01)90346-1
• 作为产物：
  描述：

  N-烯丙基乙酰胺 、 2,3-二溴-1-丙烯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到N-(2-bromo-2-propen-1-yl)-N-(2-propen-1-yl)acetamide
  参考文献：
  名称：

  The regioselectivity of rhodium and palladium-catalysed cyclisations of 2-bromo-1,6- and -1,7-dienes

  摘要：

  DOI：

  10.1016/s0040-4020(01)90346-1

文献信息

• Convenient Synthesis of Heterobicycles by Domino Heck−Diels−Alder Reactions
  作者：Laxminarayan Bhat、Arno G. Steinig、Ruth Appelbe、Armin de Meijere

  DOI：10.1002/1099-0690(200105)2001:9<1673::aid-ejoc1673>3.0.co;2-g

  日期：2001.5

  Palladium(0)-catalyzed intramolecular cross coupling of bromodialkenylamines, bromoalkenylalkenamides and bromodialkenyl ethers followed by in situ [4+2] cycloaddition with suitable dienophiles gave tetrahydroisoindolines (31−73% yield), tetrahydroisoindolin-1-ones (43−51%) and hexahydrobenzo[c]furans (35−55%), and hexahydro-1H-[2]pyrindines (66−75%), respectively, each in one-pot operations.

  钯 (0) 催化的溴二烯基胺、溴烯基烯酰胺和溴二烯基醚的分子内交叉偶联，然后与合适的亲二烯体进行原位 [4+2] 环加成，得到四氢异吲哚啉（31-73% 产率），四氢异吲哚-1-酮（43%）和六氢苯并 [c] 呋喃 (35-55%) 和六氢-1H-[2] 吡啶 (66-75%) 分别在一锅操作中。
• Palladium-catalyzed cyclizations of bromodialkenyl ethers and amines
  作者：L. Shi、C. K. Narula、K. T. Mak、L. Kao、Y. Xu、R. F. Heck

  DOI：10.1021/jo00170a005

  日期：1983.11
• Nitrogen Assistance in Intramolecular Nickel-Promoted Tandem Cyclization−Quenching Processes
  作者：Daniel Solé、Yolanda Cancho、Amadeu Llebaria、Josep M. Moretó、Antonio Delgado

  DOI：10.1021/jo960677y

  日期：1996.1.1

  A diastereoselective and mild cyclization-quenching process based on the treatment of nitrogen-tethered halodienes with stoichiometric Ni(COD)(2) is described. The success of this methodology relies on the presence of a distal amino group capable of coordinating with the metal in the transient vinyl or alkylnickel species, thus controlling the diastereoselectivity of the cyclization step and preventing Ni-H beta-elimination prior to the quenching, In general, better results are obtained in cyclizations taking place via a 5-exo-trig process, and a diversity of mono- and bicyclic nitrogenated systems are afforded in high yields by the proper choice of starting halodienes and quenching reagents, The presence of 2,2'-bipyridine as a ligand results in an acceleration of the process, and in some cases, higher diastereoselectivities and/or supression of the Ni-H beta-elimination are observed.
• Intramolecular Nitrogen Assistance in the Nickel-Promoted Tandem Cyclization-Capture of Amino-Tethered Vinyl Bromides and Alkenes
  作者：Daniel Sole、Yolanda Cancho、Amadeu Llebaria、Josep M. Moreto、Antonio Delgado

  DOI：10.1021/ja00105a096

  日期：1994.12
• Suppressed β-Hydride Elimination in Palladium-Catalyzed Cascade Cyclization−Coupling Reactions:  An Efficient Synthesis of 3-Arylmethylpyrrolidines
  作者：Chi-Wan Lee、Kyung Seok Oh、Kwang S. Kim、Kyo Han Ahn

  DOI：10.1021/ol0056426

  日期：2000.5.1

  A novel type of palladium-catalyzed cascade cyclization-coupling reaction that proceeds with suppressed beta-hydride elimination has been found. One of the N-sulfonyl oxygens is suggested to coordinatively stabilize an alkylpalladium intermediate, thus preventing the intermediate from the usual beta-elimination, This is the first sequential palladium-catalyzed coupling reaction where the Suzuki and Heck reactions can compete. The reaction provides an efficient synthetic route to 4-methylene-3-arylmethylpyrrolidines, which are not readily available by other routes.