2,3,6-trimethyl-2-hepten-4-yn-6-ol | 62839-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-trimethyl-2-hepten-4-yn-6-ol
• 英文别名: 2,5,6-trimethyl-hept-5-en-3-yn-2-ol；2,5,6-Trimethylhept-5-en-3-yn-2-ol
• CAS: 62839-58-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: SXEHGPAKKSQIJO-UHFFFAOYSA-N

物化性质

• 沸点：
  56-58 °C(Press: 3 Torr)
• 密度：
  0.8970 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,6-trimethyl-2-hepten-4-yn-6-ol 在 Lindlar's catalyst 喹啉 、 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4Z)-2,3,6-trimethyl-6-(triethylsiloxy)-2,4-heptadiene
  参考文献：
  名称：

  Further demonstration of the higher reactivity of the vinyl hydrogen rather than the allyl hydrogen towards singlet oxygen

  摘要：

  在一种新的线性扭曲的1,3-二烯中，观察到乙烯氢相对于仲烯氢对单态氧的异常高反应性。

  DOI：

  10.1039/a705924h
• 作为产物：
  描述：

  4,4,5-trimethyl-5-(3-methyl-3-hydroxy-1-butynyl)-2-ethoxy-1,3-dioxolane 生成 2,3,6-trimethyl-2-hepten-4-yn-6-ol
  参考文献：
  名称：

  KIBINA I. YU.; MUSANTAEVA SH. M.; SHCHELKUNOV A. V., XIMIYA GETEROTSIKL. SOED.,(1987) N 6, 770-771

  摘要：

  DOI：

文献信息

• Further demonstration of the higher reactivity of the vinyl hydrogen rather than the allyl hydrogen towards singlet oxygen
  作者：Hajime Mori、Keiichi Ikoma、Shigeo Katsumura

  DOI：10.1039/a705924h

  日期：——

  In a new linear twisted 1,3-diene, an anomalously high reactivity of the vinyl hydrogen rather than the allyl hydrogen towards singlet oxygen is observed.

  在一种新的线性扭曲的1,3-二烯中，观察到乙烯氢相对于仲烯氢对单态氧的异常高反应性。
• Chirko,A.I. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 1457 - 1460
  作者：Chirko,A.I. et al.

  DOI：——

  日期：——
• CHIRKO A. I.; TISHCHENKO I. G.; SOSNOVSKIJ G. M.; DEREVTSOVA T. F., ZH. ORGAN. XIMII, 1977, 13, HO 8, 1579-1582
  作者：CHIRKO A. I.、 TISHCHENKO I. G.、 SOSNOVSKIJ G. M.、 DEREVTSOVA T. F.

  DOI：——

  日期：——
• KIBINA I. YU.; MUSANTAEVA SH. M.; SHCHELKUNOV A. V., XIMIYA GETEROTSIKL. SOED.,(1987) N 6, 770-771
  作者：KIBINA I. YU.、 MUSANTAEVA SH. M.、 SHCHELKUNOV A. V.

  DOI：——

  日期：——
• Photosensitized Oxygenation of Twisted 1,3-Dienes:  Abnormally Higher Reactivity of Vinyl Hydrogen Rather than Allyl Hydrogen toward Singlet Oxygen
  作者：Hajime Mori、Keiichi Ikoma、Sachihiko Isoe、Kazuo Kitaura、Shigeo Katsumura

  DOI：10.1021/jo980955o

  日期：1998.11.1

  As one of the novel examples to investigate the characteristic reactivity of significantly twisted 1,3-dienes, the photosensitized oxygenation of two types of significantly twisted 1,3-dienes, cis-beta-ionol derivative 2 and acyclic derivative Il, is investigated. Photosensitized oxygenation of 2a-f and 11a-e revealed that the vinyl hydrogen Ha was more reactive than the allyl hydrogen Hb. Thus, phenyl derivative 2e and tert-butyl-substituted compound lid selectively produced allenes 3e and 13d in 67% and 75% yield resulting from the ene reaction of the vinyl hydrogen Ha rather than allyl alcohols 4e and 14d resulting from the allyl hydrogen abstraction in 24% and 8% yield, respectively. Furthermore, in the case of methyl-substituted compound 11b, the extent of the inherent reactivity of the vinyl hydrogen Ha was similar to that of the allyl hydrogen He. On the basis of X-ray analysis and NIM and MO calculations, the discovered abnormally higher reactivity of the vinyl hydrogen would be rationalized by considering mainly the large sigma*-pi orbital interaction between the vinyl C-H bond and another double bond in significantly twisted 1,3-dienes resulting from calculations of HOMO electron densities.