4,5-dimethyl-cis-Δ⁴-tetrahydrophthalyl alcohol | 155490-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-dimethyl-cis-Δ⁴-tetrahydrophthalyl alcohol
• 英文别名: cis-4,5-bis(hydroxymethyl)-1,2-dimethylcyclohexene；4r,5c-bis-hydroxymethyl-1,2-dimethyl-cyclohexene；4r,5c-Bis-hydroxymethyl-1,2-dimethyl-cyclohexen；[(1S,6R)-6-(hydroxymethyl)-3,4-dimethylcyclohex-3-en-1-yl]methanol
• CAS: 155490-01-0
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: JGYIRZBVMMEUQB-AOOOYVTPSA-N

物化性质

• 熔点：
  74 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  140 °C(Press: 0.6 Torr)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-cis-Δ⁴-tetrahydrophthalyl alcohol 在 迭氮酸 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 7.0h， 生成 cis-4,5-bis(aminomethyl)-1,2-dimethylcyclohexene
  参考文献：
  名称：

  Synthesis and Fungicidal Activity of Alicyclic Diamines

  摘要：

  As part of an ongoing program of work on polyamine analogues, a number of alicyclic diamines were synthesized and examined for fungicidal activity. The alicyclic diamine 1,2-bis(aminomethyl)4,5-dimethylcyclohexa-1,4-diene (BAD), synthesized as the dihydrochloride salt, controlled the important crop pathogen Erysiphe graminis f.sp hordei. Greatest control off, graminis was achieved when BAD was applied 2 days postinoculation. The alicyclic diamines trans-4,5-bis(aminomethyl)1,2-dimethylcyclohex-1-ene (trans-BAD) and the cis-isomer (cis-BAD), as well as 1,2-bis(aminomethyl)cyclopentene (BACP) and trans-1,2-bis(dimethylaminomethyl)cyclo (TCCBM), were also synthesized as their dihydrochloride salts. trans-BAD was found to possess greater fungicidal activity than the cis-isomer against E. graminis, while BACP and TCCBM both gave >80% control of powdery mildew infection. Since the powdery mildew fungus cannot be grown axenically, the effects of the alicyclic diamines on polyamine metabolism were examined using the oat leaf stripe pathogen, Pyrenophora avenae. BAD and derivatives had little effect on polyamine metabolism in the fungal pathogen P. avenae. It seems clear, therefore, that the antifungal activity of these derivatives may not be associated with altered polyamine metabolism.

  DOI：

  10.1021/jf950772s
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 4,5-dimethyl-cis-Δ⁴-tetrahydrophthalyl alcohol
  参考文献：
  名称：

  Buchta; Scheuerer, Chemische Berichte, 1956, vol. 89, p. 1002,1011

  摘要：

  DOI：

文献信息

• Phase selectively soluble dendrimer-bound osmium complex: a highly effective and easily recyclable catalyst for olefin dihydroxylationElectronic supplementary information (ESI) available: synthesis details, characterization of the osmium complexes, dihydroxylation and recycling procedure. See http://www.rsc.org/suppdata/cc/b4/b401994f/
  作者：Wei-Jun Tang、Nian-Fa Yang、Bing Yi、Guo-Jun Deng、Yi-Yong Huang、Qing-Hua Fan

  DOI：10.1039/b401994f

  日期：——

  A new switched biphasic catalysis system for highly effective olefin dihydroxylation has been described, in which the dendritic osmium catalyst preferred to dissolve in the non-polar organic layer and could be easily separated from the polar diol products through phase separation induced by addition of water at the end of the reaction.

  报道了一种新型切换双相催化系统，用于高效烯烃双羟基化反应，在该系统中，树枝状锇催化剂偏好溶于非极性有机层，并通过反应结束时加入水引起的相分离，可轻松地从极性二醇产物中分离出来。
• Cyclic Dienes. VI. Synthesis of Substituted 1,2-Dimethylenecyclohexanes^1,2
  作者：William J. Bailey、Joseph Rosenberg、Lewis J. Young

  DOI：10.1021/ja01637a068

  日期：1954.4