3-bromo-2,4-dimethyl-2-penten-4-ol | 53422-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-bromo-2,4-dimethyl-2-penten-4-ol
• 英文别名: 3-bromo-2,4-dimethyl-pent-3-en-2-ol；3-Bromo-2,4-dimethylpent-3-en-2-ol
• CAS: 53422-93-8
• 化学式: C₇H₁₃BrO
• 分子量: 193.084
• InChiKey: NLMXZSOHTLSIHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  3-bromo-2,4-dimethyl-2-penten-4-ol 在 palladium on activated charcoal 四(三苯基膦)钯 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (3Z)-5-isopropylidene-2,6-dimethyl-2-(triethylsiloxy)-3-hepten-6-ol
  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：

  2,2,3,3-tetramethyl-1,1-dibromocyclopropane 在 水 、 calcium carbonate 作用下， 以 丙酮 为溶剂， 生成 3-bromo-2,4-dimethyl-2-penten-4-ol
  参考文献：
  名称：

  Santelli,C.; Bertrand,M., Bulletin de la Societe Chimique de France, 1974, p. 605 - 608

  摘要：

  DOI：

文献信息

• Warner, Philip M.; Le, Diem, Synthetic Communications, 1984, vol. 14, # 14, p. 1341 - 1348
  作者：Warner, Philip M.、Le, Diem

  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.