1,1,4,4-Tetra-tert-butyl-1,3-butadien | 166047-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,4,4-Tetra-tert-butyl-1,3-butadien
• 英文别名: all-trans-1,1,4,4-tetra(tert-butyl)buta-1,3-diene；3,6-Di-tert-butyl-2,2,7,7-tetramethyl-3,5-octadien；3,6-Ditert-butyl-2,2,7,7-tetramethylocta-3,5-diene
• CAS: 166047-11-6
• 化学式: C₂₀H₃₈
• 分子量: 278.522
• InChiKey: XESOHRPETHMNOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1,1,4,4-Tetra-tert-butyl-1,3-butadien 在 2-氯苯亚甲基丙二腈 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Radical Anions of Sterically Protected Polyenes: An ESR and ENDOR Study

  摘要：

  Owing to the steric protection by four bulky substituents in the terminal positions 1 and n, several conjugated polyenes could be reduced with K or Cs metal in 12-dimethoxyethane (DME)or tetrahydrofuran (THF) to fairly persistent radical anions. These compounds denoted here as 2, 3,...7 (which corresponds to the number. 1/2 n=2. 3,...7. of their formal double bonds) are 1,1,1,n,n-tetra(tert-butyl) derivatives of buta-1,3-diene, hexa-1,3,5-triene. octa-1,3,5,7-tetraene; deca-1,3,5,7,9-pentaene, dodeca-1,3,5,7,Sr,11-hexaene, and tetradeca-1,3,5,7,9,11,13-heptaene. in addition to the six polyenes 2- 7 with all-trans-configuration, the studies comprised an isomer of 3, the trans,cis,trans-trienc. c-3. The radical anions 2(.-)-7(.-) and c-3(.-) were characterized by their hyperfine data acquired with ESR, ENDOR. and TRIPLE-resonance spectroscopy. The H-1-coupling constants comply with the spin distribution predicted for the radical anions of such 'linear' pi-systems by simple MO models. ion pairs formed with K+ in DME were loose but became tighter with Cs+ in THF. Propensity to ion pairing decreased with the lengthening of the pi-system on going from 2(.-) to 3(.-)-7(.-). Hyperfine data are likewise reported for the radical anions of all-trans-polyenes 8 and 9. in which two tert-butyl substituents in one terminal position of 2 and, respectively, were replaced by CN groups.

  DOI：

  10.1002/(sici)1522-2675(19990804)82:8<1266::aid-hlca1266>3.0.co;2-h
• 作为产物：
  描述：

  3,6-di-tert-butyl-2,2,7,7-tetramethyloct-4-yn-3,6-diol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 792.0h， 以16%的产率得到
  参考文献：
  名称：

  Hopf, Henning; Haenel, Ralf; Jones, Peter G., Angewandte Chemie, 1994, vol. 106, # 13, p. 1444 - 1445

  摘要：

  DOI：

文献信息

• The chemical behavior of terminally <i>tert</i>-butylated polyolefins
  作者：Dagmar Klein、Henning Hopf、Peter G Jones、Ina Dix、Ralf Hänel

  DOI：10.3762/bjoc.11.139

  日期：——

  saturated hydrocarbon 10. Bromine addition to 3 and 7 yielded the dibromides 17 and 18, respectively, i.e., the oligoene system has been attacked at its terminal olefinic carbon atoms. Analogously, the higher vinylogs 19 and 20 yielded the 1,8- and 1,10-bromine adduts 23 and 24, respectively, when less than 1 equivalent of bromine was employed. Treatment of tetraene 19 with excess bromine provided tetrabromide

  已经研究了各种低聚物2的化学行为。二烯3的催化加氢产生单烯4。三烯7加氢成二烯8，单烯9和饱和烃10。向3和7中溴加成分别生成二溴化物17和18，即，低聚烯烃体系在其上受到攻击。末端烯烃碳原子。类似地，当使用少于1当量的溴时，高级乙烯基化合物19和20分别产生1，8-和1，10-溴加成物23和24。用过量的溴处理四烯19提供四溴化物25。在环氧化反应中，与间氯过苯甲酸（MCPBA）和二甲基二环氧乙烷（DMDO）一起研究了两种低聚模型：三烯7和四烯19。而7则为重排产物31提供了MCPBA。 ，得到带有DMDO的对称环氧化物32。类似地，用MCPBA将19转化为单环氧化物33，用DMDO转化为34。没有与N-苯基三唑啉二酮（PTAD）进行Diels-Alder加成7。将共轭π-体系扩展至下一个更高的乙烯基，19，以良好的收率将NPTD加到对称加合物37上。在向戊烯20和己烯21中添加NPTD