1,1,1-trideutero-3-methyl-2-butene | 1560-58-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,1,1-trideutero-3-methyl-2-butene
• 英文别名: 2-methyl-2-butene-4,4,4-d3；1,1,1-trideuterio-3-methyl-but-2-ene；1,1,1-Trideutero-3-methyl-but-2-en；Trimethylethylen-d3；1,1,1-Trideuterio-3-methylbut-2-ene
• CAS: 1560-58-3
• 化学式: C₅H₁₀
• 分子量: 73.1106
• InChiKey: BKOOMYPCSUNDGP-FIBGUPNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  二碘甲烷 、 1,1,1-trideutero-3-methyl-2-butene 在 diethylzinc 作用下， 以 甲苯 为溶剂， 生成 1,1-dimethyl-2-(methyl-d3)cyclopropane
  参考文献：
  名称：

  Cyclopropane intermediates in the rearrangement and fragmentation of olefinic molecular ions

  摘要：

  AbstractMethyl loss from deuterium‐labelled molecular ions of 4‐methyl‐2‐pentene, 2‐methyl‐2‐pentene and 1,1,2‐trimethylcyclopropane has been investigated for metastable molecular ions and for molecular ions formed by charge exchange with COS+˙, XE+˙ and CO+˙. For metastable ion fragmentation reactions all three compounds exhibit very similar behavior and show specific and essentially equal loss of each of the original methyl groups as well as specific loss of a methyl where the hydrogens derive exclusively from the non‐methyl hydrogens of the original molecules. The former results are interpreted in terms of interconversion of the three molecular ions through a ring‐opened form of the trimethylcyclopropane molecular ion. The loss of the non‐methyl hydrogens as CH3 is interpreted in terms of isomerization to the 2,3‐dimethyl‐2‐butene structure. With increasing internal energy direct allylic cleavage of the unrearranged methylpentene molecular ions increases in importance while the trimethylcyclopropane molecular ion shows an increased preference for loss of the C(2) methyl group. With increasing internal energy loss of the original non‐methyl hydrogens as CH3 decreases markedly in importance.

  DOI：

  10.1002/oms.1210201007
• 作为产物：
  描述：

  2-methylbutan-2-ol-4,4,4-d3 在 氢气 作用下， 生成 1,1,1-trideutero-3-methyl-2-butene
  参考文献：
  名称：

  Cyclopropane intermediates in the rearrangement and fragmentation of olefinic molecular ions

  摘要：

  AbstractMethyl loss from deuterium‐labelled molecular ions of 4‐methyl‐2‐pentene, 2‐methyl‐2‐pentene and 1,1,2‐trimethylcyclopropane has been investigated for metastable molecular ions and for molecular ions formed by charge exchange with COS+˙, XE+˙ and CO+˙. For metastable ion fragmentation reactions all three compounds exhibit very similar behavior and show specific and essentially equal loss of each of the original methyl groups as well as specific loss of a methyl where the hydrogens derive exclusively from the non‐methyl hydrogens of the original molecules. The former results are interpreted in terms of interconversion of the three molecular ions through a ring‐opened form of the trimethylcyclopropane molecular ion. The loss of the non‐methyl hydrogens as CH3 is interpreted in terms of isomerization to the 2,3‐dimethyl‐2‐butene structure. With increasing internal energy direct allylic cleavage of the unrearranged methylpentene molecular ions increases in importance while the trimethylcyclopropane molecular ion shows an increased preference for loss of the C(2) methyl group. With increasing internal energy loss of the original non‐methyl hydrogens as CH3 decreases markedly in importance.

  DOI：

  10.1002/oms.1210201007

文献信息

• Direct, Chemoselective<i>N</i>-<i>tert</i>-Prenylation of Indoles by CH Functionalization
  作者：Michael R. Luzung、Chad A. Lewis、Phil S. Baran

  DOI：10.1002/anie.200902761

  日期：2009.9.7

  Four steps in one: The direct prenylation of indoles at N‐1 can be achieved by CH functionalization in the presence of a PdII source. This reaction proceeds by direct intermolecular olefin amination, tolerates a broad range of functional groups, and can be carried out on a gram scale, as demonstrated by the formal syntheses of a number of natural products and the synthesis of an antifungal natural

  四步合一：在 Pd II源存在下，通过 C  H 功能化可以实现 N-1 上吲哚的直接异戊二烯化。该反应通过直接分子间烯烃胺化进行，耐受范围广泛的官能团，并且可以在克规模上进行，如许多天然产物的正式合成和抗真菌天然产物的合成所证明的（参见方案）。
• GRDINA M. B.; ORFANOPOULOS M.; STEPHENSON L. M., J. ORG. CHEM., 1979, 44, NO 16, 2936-2938
  作者：GRDINA M. B.、 ORFANOPOULOS M.、 STEPHENSON L. M.

  DOI：——

  日期：——