N-Benzyl-N-(2-bromoallyl)-2-cyclohexenylamine | 160929-09-9

• 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-Benzyl-N-(2-bromoallyl)-2-cyclohexenylamine
• 英文别名: N-benzyl-N-(2-bromoprop-2-enyl)cyclohex-2-en-1-amine
• CAS: 160929-09-9
• 化学式: C₁₆H₂₀BrN
• 分子量: 306.245
• InChiKey: FSDUUYBHBSORJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-Benzyl-N-(2-bromoallyl)-2-cyclohexenylamine 在 trisodium tris(3-sulfophenyl)phosphine 、 N,N-二异丙基乙胺 、 palladium dichloride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以77%的产率得到(3aRS,7aRS)-N-benzyl-3-methylene-2,3,3a,6,7,7a-hexahydro-1H-indole
  参考文献：
  名称：

  水性介质中的分子内Heck型反应。区域选择性的巨大变化

  摘要：

  使用水溶性Pd / TPPTS催化剂在水性介质中进行高效的分子内Heck型环化反应。在这些条件下，通常观察到的外切过程被逆转，有利于内环化化合物的区域选择性形成。

  DOI：

  10.1016/0040-4039(96)00253-5
• 作为产物：
  描述：

  N-(2-bromoallyl)benzylamine 、 3-溴环己烯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以85%的产率得到N-Benzyl-N-(2-bromoallyl)-2-cyclohexenylamine
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles

  摘要：

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.

  DOI：

  10.1002/chem.19970030820

文献信息

• 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
• Zirconium-Mediated Intramolecular Coupling of Terminal Alkynes and Their Subsequent Carbonylation: Novel Synthesis of Seven- and Eight-Membered Heterocycles
  作者：José Barluenga、Roberto Sanz、Francisco J. Fañanás

  DOI：10.1002/chem.19970030820

  日期：1997.8

  AbstractThe development of a new method for the intramolecular coupling of terminal alkynes and for the synthesis of seven‐ and eight‐membered benzoheterocycles is reported. The key steps involve the generation of zirconocene‐alkyne complexes from 2‐bromoalkenes and the subsequent intramolecular carbometalation of olefins or acetylides. The 8‐unsubstituted zirconabicyclopentenes were carbonylated to afford unexpected products and allow access to polyfunctionalized molecules from simple starting materials.
• Intramolecular Heck-type reactions in aqueous medium. Dramatic change in regioselectivity
  作者：Sandrine Lemaire-Audoire、Monique Savignac、Christophe Dupuis、Jean-Pierre Genêt

  DOI：10.1016/0040-4039(96)00253-5

  日期：1996.3

  Efficient intramolecular Heck-type cyclizations were carried out in aqueous medium using water-soluble Pd/TPPTS catalysts. Under these conditions, the generally observed exo process was reversed in favor of the regioselective formation of endo cyclized compounds.

  使用水溶性Pd / TPPTS催化剂在水性介质中进行高效的分子内Heck型环化反应。在这些条件下，通常观察到的外切过程被逆转，有利于内环化化合物的区域选择性形成。