(Pentene-4' yl)-2 N,N-dimethylbenzylamine | 127563-75-1

• 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: (Pentene-4' yl)-2 N,N-dimethylbenzylamine
• 英文别名: 2-(pent-4'-enyl)-N,N-dimethylaminomethylbenzene；N,N-dimethyl-1-(2-pent-4-enylphenyl)methanamine
• CAS: 127563-75-1
• 化学式: C₁₄H₂₁N
• 分子量: 203.327
• InChiKey: NCEUBDROMHPVHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  palladium diacetate 、 (Pentene-4' yl)-2 N,N-dimethylbenzylamine 以 苯 为溶剂， 以67%的产率得到
  参考文献：
  名称：

  Allyl versus aryl C-H activation mediated by palladium acetate

  摘要：

  In the presence of a catalytic amount of palladium acetate and a 2.1 stoichiometry of 1,4-benzoquinone, N,N-dimethyl-2-propenylbenzenemethylamine afforded N, N-dimethyl-2-benzazepinium in up to 85% yield. Under similar conditions related N,N-dimethyl-2-propenylbenzenamine and N,N-dimethyl-2-butenylbenzene-methylamin afforded the quinolinium and the isoquinolinium derivatives with 85 and 21% yields, respectively. Running these reactions in the presence of stoichiometric amounts of palladium acetate led to the formation of cyclopalladated compounds formed by the orthopalladation of the aryl ring. Thus, under these latter conditions the aromatic C-H activation is in competition with the allylic one. (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(97)00450-6
• 作为产物：
  描述：

  2,2-dimethyl-2,3,4,5,6,7-hexahydro-1H-2-benzazonium iodide 在 AgOH 、 水 作用下， 生成 (Pentene-4' yl)-2 N,N-dimethylbenzylamine 、 4-Penten-1-amine, N,N-dimethyl-5-(2-methylphenyl)-
  参考文献：
  名称：

  Elmasmodi, Abdellatif; Barbry, Didier; Hasiak, Bruno, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 10, p. 2767 - 2774

  摘要：

  DOI：

文献信息

• Study of the reaction of sodium amide in liquid ammonia with hexahydro-(1h)-2-benzazoninium salts : access to 2-aza-(7)-metacyclophanes
  作者：Didier Barbry、Damien Spanneut、Bruno Hasiak、Daniel Couturier

  DOI：10.1016/0040-4020(91)80006-n

  日期：1991.1

  The rearrangement of hexahydro-(1H)-2-benzazoninium ylides in liquid ammonia yields a mixture of amines : metacyclophanes arise from Sommelet-Hauser transposition, alkenes from an Hofmann elimination, enamines from a process which is discussed here, and two other minor compounds from a Stevens shift. Dynamic NMR of azametacyclophanes will be discussed .

  液态氨中六氢-（1H）-2-苯甲氮鎓烷基化物的重排产生了胺的混合物：偏环环烷烃由Sommelet-Hauser转座产生，烯烃由霍夫曼消除产生，烯胺来自此处讨论的方法，以及另外两种较小的化合物从史蒂文斯转变。氮杂甲基环烷的动态NMR将会进行讨论。
• Palladium-Mediated Intramolecular C-N Bond Formation between Tertiary Amines and Alkenes
  作者：Paul A. van der Schaaf、Jean-Pascal Sutter、Mary Grellier、Guido P. M. van Mier、Anthony L. Spek、Gerard van Koten、Michel Pfeffer

  DOI：10.1021/ja00091a016

  日期：1994.6

  The reaction of terminal alkenylarenes having either o-(dimethylamino) or o-[(dimethylamino)methyl] substituents with PdCl2(MeCN)(2) in MeOH in the presence of NaOAc and PPh(3) has been studied. This reaction affords allylic phosphonium compounds for those substrates having more than six carbon atoms between the alkene function and the tertiary amine nitrogen atom, In those cases where the alkene is closer to the NMe(2) unit, this reaction leads, via allylic metalation, to intramolecular cyclization that involves generation of a new C-N bond and results in the formation of cationic 5-, 6-, or 7-membered heterocyclic ammonium compounds. For example, C6H4(CH2CH=CH2)-1-(CHMeNMe(2))-2 can be converted to the endo-cyclization product [C6H4CH=CHCH(2)NMe(2)CH(Me)}-1,2]Cl in 86% yield with this Pd(II)-based system. The cyclization reaction is highly selective and occurs either at the terminal, less substituted olefinic carbon atom (C-gamma), affording ende-cyclization, or at the allylic C-alpha carbon atom, resulting in the formation of exo-cyclic products. The cyclization reaction is thought to proceed via a palladium-assisted C-H activation route: in most cases it was possible to isolate and characterize an eta(3)-allylpalladium complex as a key intermediate and then allow it to react further with PPh(3) to afford a cyclized end product. The X-ray crystal structures of a palladium-allyl complex, i.e., 2i(syn), and a quinolinium derivative, 3a, are described. Crystal data for 2i(syn): monoclinic, space group P2(1)/c, with a = 8.902(1), b = 20.587(1), and c = 9.702(1) Angstrom, beta = 95.52(1)degrees, Z = 4, R = 0.038. Crystal data for 3a: monoclinic, space group P2(1)/n with a = 13.032(1), b = 6.544(1), and c 13.415(1) Angstrom, beta = 114.72(1)degrees, Z = 4, R = 0.042,