1-(N-烯丙基-N-苄基氨基)-2-甲基-2-丙烯 | 143104-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(N-烯丙基-N-苄基氨基)-2-甲基-2-丙烯
• 英文名称: N-allyl-N-benzyl-N-(2-methylallyl)amine
• 英文别名: N-benzyl-2-methyl-N-prop-2-enylprop-2-en-1-amine
• CAS: 143104-59-0
• 化学式: C₁₄H₁₉N
• 分子量: 201.312
• InChiKey: KVERMEYIDHGEHB-UHFFFAOYSA-N

物化性质

• 沸点：
  263.3±9.0 °C(Predicted)
• 密度：
  0.921±0.06 g/cm3(Predicted)

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：
  0.29
• 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：

  1-(N-烯丙基-N-苄基氨基)-2-甲基-2-丙烯 在 正丁基锂 、 zirconocene dichloride 、 氘代甲醇 、 碳酸氢钠 作用下， 以 四氢呋喃 、 正己烷 、 甲醇 为溶剂， 反应 17.0h， 生成 1-benzyl-3-deuteriomethyl-3,4-dimethylpyrrolidine
  参考文献：
  名称：

  The regiochemistry of zirconacycle elaboration

  摘要：

  The regioselectivity of insertion of carbenoids into a variety of unsymmetrical zirconacyclopentanes is reported. For comparison the regioselectivities of isonitrile insertion and protonation have also been determined. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.105
• 作为产物：
  描述：

  (E)-N-烯丙基-1-苯基甲亚胺 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 1-(N-烯丙基-N-苄基氨基)-2-甲基-2-丙烯
  参考文献：
  名称：

  Investigations concerning the organolanthanide and group 3 metallocene-catalyzed cyclization–functionalization of nitrogen-containing dienes

  摘要：

  Organolanthanide catalyzed cyclization-silylation of nitrogen-containing polyunsaturated systems allows access to core structures commonly found in naturally occurring alkaloids. Nitrogen-containing dienes with various substitution patterns were investigated. The method was most successful for substrates with terminal alkenes. Cyclization upon pendant 1,1-disubstituted olefins was not realized under various conditions. Interestingly, sterically hindered sulfonamides, which were previously believed to render the catalyst inactive, were actually compatible with the catalyst, thus affording the cyclized products after prolonged reaction times. Variations using fused ring systems were also investigated. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.048

文献信息

• Tandem Insertion of Halocarbenoids and Lithium Acetylides into Zirconacycles: A Novel Rearrangement to Zirconium Alkenylidenates by β-Addition to an Alkynyl Zirconocene
  作者：Jozef Stec、Emma Thomas、Sally Dixon、Richard J. Whitby

  DOI：10.1002/chem.201002962

  日期：2011.4.18

  Tandem insertion of 1,1‐dihalo‐1‐lithio species (halocarbenoids) and lithium alkynides into zirconacyclopentenes and zirconcyclopentanes affords carbocyclic products in high yields via an unusual rearrangement that probably involves addition of an organolithium species to the β‐position of a zirconium–alkyne complex to give an alkenylidene–zirconate species. A wide variety of cyclopentanoid organic

  将1,1–二卤代1–硫代化合物（卤代类固醇）和炔属锂串联插入到氧化锆环戊烯和锆环戊烷中可以通过不寻常的重排提供高收率的碳环产物，该重排可能涉及将有机锂物种添加到锆的β位上。炔烃复合物，可得到烯基-锆酸酯。使用这种多组分偶联剂，可以高产率快速组装各种各样的环戊烷类有机结构。在某些情况下，主要的副反应是β-氢化物消除中间的环戊基或环戊烯基锆茂。
• The Regiochemistry of Carbenoid Insertion into Zirconacycles
  作者：George J. Gordon、Tim Luker、Mark W. Tuckett、Richard J. Whitby

  DOI：10.1016/s0040-4020(99)01094-7

  日期：2000.4

  lithium chloroallylides (allyl carbenoids) into a wide variety of unsymmetrical zirconacycles has been determined. In all but one case a single regioisomer was obtained. A combination of steric and electronic effects is needed to explain the results and imply that the carbenoid is acting predominantly as an electrophilic species. The first carbenoid insertion into a zirconacyclopentadiene is noted.

  已经确定了将氯代烯丙基锂（烯丙基类胡萝卜素）插入各种各样的不对称氧化锆环中的区域选择性。除一种情况外，在所有情况下均获得单一的区域异构体。需要结合空间和电子效应来解释结果，并暗示类胡萝卜素主要起亲电物质的作用。注意到第一次类胡萝卜素插入到氧化锆环戊二烯中。
• Pyrrole synthesis using a tandem Grubbs’ carbene–RuCl3 catalytic system
  作者：Nicolai Dieltiens、Christian V. Stevens、David De Vos、Bart Allaert、Renata Drozdzak、Francis Verpoort

  DOI：10.1016/j.tetlet.2004.10.044

  日期：2004.11

  A straightforward pyrrole synthesis from diallylamines is developed by using a tandem catalyst system leading to ring-closing metathesis with the second generation Grubbs' catalyst (10%) followed by dehydrogenation in the presence of RuCl3 x H2O (2%). (C) 2004 Elsevier Ltd. All rights reserved.
• Fu, Gregory C.; Grubbs, Robert H., Journal of the American Chemical Society, 1992, vol. 114, # 18, p. 7324 - 7325
  作者：Fu, Gregory C.、Grubbs, Robert H.

  DOI：——

  日期：——
• Synthesis of Heterocycles Using Zirconium-Catalyzed Asymmetric Diene Cyclization
  作者：Yousuke Yamaura、Masaru Hyakutake、Miwako Mori

  DOI：10.1021/ja964462h

  日期：1997.8.1