1-deutero-2-methylnonane | 1392012-09-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: 1-deutero-2-methylnonane
• 英文别名: 1-deutero-3-methylnonane；1-Deuterio-3-methylnonane
• CAS: 1392012-09-7
• 化学式: C₁₀H₂₂
• 分子量: 143.277
• InChiKey: PLZDDPSCZHRBOY-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  在 重水 、 氘代盐酸 作用下， 以 正己烷 为溶剂， 生成 1-deutero-2-methylnonane
  参考文献：
  名称：

  The tantalum-catalyzed carbozincation of 1-alkenes with zinc dialkyls

  摘要：

  The TaCl5-mediated reaction between monosubstituted alkenes and Et2Zn affords 3-(R-substituted)-n-butylzincs in high yield (up to 92%) and regioselectivity. Organozinc reagents bearing a longer alkyl chain (R = Pr-n, Bun, Am-n, Hex(n)) react with 1-alkenes in the presence of TaCl5 as the catalyst to give two types of organozinc compound having iso-alkyl structure. The probable mechanism of the carbozincation reaction implies the formation of beta-substituted and beta,beta'-disubstituted tantalacyclopentanes as the key intermediates. The thermodynamic probability of the mechanistic elementary stages for the ethylzincation of terminal alkenes has been estimated using DFT PBE/SBK method. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.039

文献信息

• Unusual pathway of the tantalum-catalyzed carboalumination reaction of alkenes with triethylaluminum
  作者：Rifkat M. Sultanov、Elena V. Samoilova、Natal’ya R. Popod’ko、Artur R. Tulyabaev、Denis Sh. Sabirov、Usein M. Dzhemilev

  DOI：10.1016/j.tetlet.2013.09.121

  日期：2013.11

  TaCl5 results in a mixture of 2-(R-substituted)- and 3-(R-substituted)-n-butylaluminums (1:1 ratio) in total yields of 75–85%. The TaCl5-catalyzed reaction of bicyclo[2.2.1]hept-2-ene, endo-tricyclo[5.2.1.02,6]deca-3,8-diene, and (exo/endo)-5-methylbicyclo[2.1.1]hept-2-ene with Et3Al leads to the formation of diethyl[2-exo-(2′-norbornylethyl)]aluminums in high yields. DFT calculations confirm the thermodynamic

  的1-烯烃（1-己烯，1-辛烯，1-癸烯）用Et碳铝化3的Al在催化量的TACL的存在5次中的2-混合物的结果（[R和3-（ -取代的）- [R -取代的）-正丁基铝（1：1比例），总产率为75-85％。TACl 5催化的双环[2.2.1]庚-2-烯，内-三环[5.2.1.0 2,6 ] deca-3,8-二烯和（外/内）-5-甲基双环[2.1]的反应.1]庚-2-烯与Et 3 Al导致形成二乙基[2- exo]-（2'-降冰片基乙基）]铝的产率很高。DFT计算证实了最终exo产品的热力学偏好。还讨论了通过钽-环戊烷作为关键中间体形成有机铝的多步反应机理。
• Zirconium-catalyzed reaction of terminal alkenes with triethylindium
  作者：I. R. Ramazanov、L. K. Dil’mukhametova、U. M. Dzhemilev

  DOI：10.1134/s1070428013090017

  日期：2013.9

  Terminal alkenes (undec-1-ene, oct-1-ene, and allylbenzene) reacted with triethylindium in the presence of a catalytic amount of Cp2ZrCl2 in hexane to give mixtures of three organoindium compounds whose hydrolysis in D2O afforded 2-substituted 1,4-dideuterobutane containing minor amounts of 2-substituted 1- and 4-deuterobutanes.

  在催化量的Cp 2 ZrCl 2在己烷中的存在下，末端烯烃（十一碳烯，十一碳烯和烯丙基苯）与三乙基铟反应，得到三种有机铟化合物的混合物，在D 2 O中水解得到2含有少量2-取代的1-和4-氘代丁二酮的1-取代的1，4-二氟代丁烷丁烷。
• Two routes of tantalum-catalyzed alkene carbomagnesiation with ethyl Grignard reagents
  作者：Rifkat M. Sultanov、Usein M. Dzhemilev、Elena V. Samoilova、Ruslan R. Ismagilov、Leonard M. Khalilov、Natal'ya R. Popod'ko

  DOI：10.1016/j.jorganchem.2012.05.023

  日期：2012.9

  Carbomagnesiation of 1-alkenes with EtMgX (X = Cl, Et) has been implemented in the presence of TaCl5 as a catalyst to give a mixture of 2-(R-substituted)-and 3-(R-substituted)-n-butylmagnesiums (5: 4 ratio) ina total yield of 98%. The probable mechanism of their formation through tantalacyclopentanes as key intermediates is discussed. (C) 2012 Elsevier B. V. All rights reserved.