1-ethyl-2,3-dipropylaluminacyclopent-2-ene | 146000-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 1-ethyl-2,3-dipropylaluminacyclopent-2-ene
• CAS: 146000-05-7
• 化学式: C₁₂H₂₃Al
• 分子量: 194.296
• InChiKey: KMXSUGPHDOXTCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-ethyl-2,3-dipropylaluminacyclopent-2-ene 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 1-phenyl-4,5-dipropyl-2,3-dihydro-1H-phosphole 1-sulfide
  参考文献：
  名称：

  Targeted synthesis of 2,3-disubstituted 2-phospholenes using catalytic cycloalumination of acetylenes

  摘要：

  A preparative one-pot method for the synthesis of 2,3-dialkyl-substituted phosphol-2-enes by catalytic cycloalumination of symmetric acetylenes with AlEt3 catalyzed by Cp2ZrCl2 is developed. The reaction gives the corresponding aluminacyclopentenes, which then react in situ with phosphorus dihalides. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.029
• 作为产物：
  描述：

  5-癸炔 、 三乙基铝 在 二氯二茂锆 作用下， 以 正己烷 为溶剂， 反应 8.0h， 生成 1-ethyl-2,3-dipropylaluminacyclopent-2-ene
  参考文献：
  名称：

  Synthesis of substituted 2,3-dihydro-1H-boroles by transmetalation of aluminacyclopent-2-enes with BF3·Et2O

  摘要：

  A procedure was developed for selective synthesis of 4,5-dialkyl-1-fluoro-2,3-dihydro-1H-boroles via transmetalation of the corresponding aluminacyclopent-2-enes with BF3 center dot Et2O. 4,5-Dialkyl-1-fluoro-2,3-dihydro-1H-boroles were isolated as complexes with BEtF2. 4-Alkyl-5-dimethylaminomethyl-1-fluoro-2,3-dihydro-1H-boroles were synthesized for the first time.

  DOI：

  10.1134/s1070428012060024

文献信息

• Allyl and 2-Cyclopropylethyl Rearrangements in the Reaction of 1-Alkenylaluminums with Diiodomethane/Triethylaluminum Reagent
  作者：Ilfir Ramazanov、Alsu Yaroslavova、Niyaz Yaubasarov、Usein Dzhemilev

  DOI：10.1055/s-0036-1591731

  日期：2018.3

  The reaction of diiodomethane and triethylaluminum with substituted 1-alkenylaluminums obtained by the Zr-catalyzed carbo- or cycloalumination of mono- or dialkyl-substituted alkynes resulted in the selective formation of di- and tetrasubstituted cyclopropanes. 1-Alkenylaluminums prepared from substituted propargylamines reacted with diiodomethane and triethylaluminum to give substituted allylamines

  二碘甲烷和三乙基铝与通过 Zr 催化的单或二烷基取代炔烃的碳或环铝化反应获得的取代 1-链烯基铝的反应导致选择性形成二和四取代的环丙烷。由取代的炔丙胺制备的 1-烯基铝与二碘甲烷和三乙基铝反应得到取代的烯丙胺。提出了 1-链烯基铝与二碘甲烷/三乙基铝反应的合理机制。
• Synthesis of halogen-substituted borolanes and 2,3-dihydro-1H-boroles by reactions of aluminacarbocycles with boron trichloride and boron tribromide
  作者：L. I. Khusainova、L. O. Khafizova、T. V. Tyumkina、U. M. Dzhemilev

  DOI：10.1134/s1070428014030014

  日期：2014.3

  A selective procedure has been developed for the synthesis of 1-chloro(bromo)-substituted borolanes and 2,3-dihydro-1H-boroles by reaction of aluminacarbocycles with boron trihalides BX3 (X = Cl, Br). 3-Substituted 1-chloro(bromo)borolanes and 2,3-dihydro-1H-boroles have been isolated as individual substances, and their structure has been determined.

  通过铝碳环化合物与三卤化硼BX 3（X = Cl，Br）的反应，已经开发出一种选择性程序，用于合成1-氯（溴）取代的硼烷和2,3-二氢-1 H-硼烷。已分离出3-取代的1-氯（溴）硼烷和2,3-二氢-1 H-硼酸酯作为单独的物质，并已确定了它们的结构。
• The efficient method for the preparation of alkenylsilanes from organoaluminums
  作者：Rita N. Kadikova、Tat'yana P. Zosim、Usein M. Dzhemilev、Ilfir R. Ramazanov

  DOI：10.1016/j.jorganchem.2014.04.004

  日期：2014.8

  aluminacyclopentanes takes place on the less sterically hindered reaction center. Using electron-donating solvents (diethyl ether, THF) inhibits the reaction. A new convenient procedure of silylation was developed, which consists in obtaining the silyl tosylate by the reaction of chlorosilanes with anhydrous sodium tosylate in toluene solution. The resulting reaction mixture was reacted with organoaluminum compounds

  磺酸的甲硅烷基酯是用于β，β-和β-取代的1-烯基铝的便捷有效的甲硅烷基化剂。反应在室温下在CH 2 Cl 2中进行用己烷或己烷洗涤18小时，以高收率得到相应的烯基硅烷。同时，在所研究的反应中，α，β-二取代和α，β，β-三取代的1-烯基铝是惰性的。与氧化铝环戊-2-烯和氧化铝环戊烷的反应发生在空间位阻较小的反应中心上。使用供电子溶剂（乙醚，THF）会抑制反应。开发了一种新的便捷的甲硅烷基化方法，该方法包括通过氯硅烷与无水甲苯磺酸钠在甲苯溶液中的反应获得甲苯磺酸甲硅烷基酯。使所得反应混合物与有机铝化合物反应，而无需分离甲苯磺酸甲硅烷基酯。
• Zirconocene Catalysis in Organoaluminum Synthesis of 1-Alkenyl Sulfones and Sulfides
  作者：Rita Kadikova、Ilfir Ramazanov、Alexey Vyatkin、Usein Dzhemilev

  DOI：10.1055/s-0036-1588387

  日期：——

  β-disubstituted 1-alkenyl sulfones and 1-alkenyl sulfides in high yields. S-Methyl methanethiosulfonate is shown to be a convenient and efficient sulfanylating agent for 1-alkenylaluminum derivatives. The Cp2ZrCl2-catalyzed methylalumination of 1-alkynyl sulfones and 1-alkynyl sulfides with Me3Al, followed by deuterolysis or hydrolysis, affords the corresponding β,β-disubstituted 1-alkenyl sulfones and

  摘要 用Me 3 Al进行Cp 2 ZrCl 2催化的1-炔基砜和1-炔基硫化物的甲基烷基化，然后进行氘解或水解，以高收率提供相应的β，β-二取代的1-烯基砜和1-烯基硫化物。甲硫代磺酸S-甲酯显示出是用于1-链烯基铝衍生物的方便和有效的磺酰化剂。 用Me 3 Al进行Cp 2 ZrCl 2催化的1-炔基砜和1-炔基硫化物的甲基烷基化，然后进行氘解或水解，以高收率提供相应的β，β-二取代的1-烯基砜和1-烯基硫化物。甲硫代磺酸S-甲酯显示出是用于1-链烯基铝衍生物的方便和有效的磺酰化剂。
• Efficient halogenation of unsaturated organoaluminum compounds with sulfonyl halides
  作者：I. R. Ramazanov、R. N. Kadikova、U. M. Dzhemilev

  DOI：10.1134/s1070428013030020

  日期：2013.3

  Alkenylalumanes prepared by carbo-or cycloalumination of substituted acetylenes reacted with an equivalent amount of sulfonyl halide (MsCl, TsCl, PhSO2Cl, MsBr) in methylene chloride or hexane at room temperature to produce alkenyl halides in high yields. Electron-donor solvents such as diethyl ether or tetrahydrofuran inhibited the halogenation process. beta-Substituted vinylalumanes generated by hydroalumination of substituted acetylenes failed to react with sulfonyl halides.