1-(3-methylbuta-1,2-dienyl)cyclohexan-1-ol | 56579-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-methylbuta-1,2-dienyl)cyclohexan-1-ol
• 英文别名: 1-(3-Methylbuta-1,2-dien-1-yl)cyclohexan-1-ol
• CAS: 56579-24-9
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: AVVUEZMUXMPBTC-UHFFFAOYSA-N

物化性质

• 沸点：
  236.1±8.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  1-(3-methylbuta-1,2-dienyl)cyclohexan-1-ol 在 葡萄糖 、 Caldariomyces fumago chloroperoxidase 、 Aspergillus niger glucose oxidase type II 、 氧气 、 sodium bromide 作用下， 以 正己烷 为溶剂， 以69%的产率得到3-bromo-2,2-dimethyl-1-oxaspiro[4.5]dec-3-ene
  参考文献：
  名称：

  烯丙醇和羧酸盐的酶促卤代化：功能化的O-杂环的生物催化进入。

  摘要：

  产自烟曲霉的氯过氧化物酶催化烯丙醇和羧酸的需氧氧化卤代环化反应，生成功能化的呋喃和吡喃杂环，作为有价值的合成支架。得益于氧化酶引发的氧化还原级联反应，...

  DOI：

  10.1039/c6gc01926a
• 作为产物：
  描述：

  3-甲基-1,2-丁二烯 、 环己酮 在 甲基锂 、 二异丙胺 作用下， 生成 1-(3-methylbuta-1,2-dienyl)cyclohexan-1-ol
  参考文献：
  名称：

  3,3-Dimethylallenyllithium. Reaction with electrophiles leading to carbenoid, electron transfer, and nucleophilic processes

  摘要：

  DOI：

  10.1021/ja00465a035

文献信息

• Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines:  Selective Synthesis of Lactones and Lactams
  作者：Eiji Yoneda、Shi-Wei Zhang、Da-Yang Zhou、Kiyotaka Onitsuka、Shigetoshi Takahashi

  DOI：10.1021/jo0350615

  日期：2003.10.1

  Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give gamma-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.
• Ruthenium-Catalyzed Cyclic Carbonylation of Allenyl Alcohols. Selective Synthesis of γ- and δ-Lactones
  作者：Eiji Yoneda、Takayuki Kaneko、Shi-Wei Zhang、Kiyotaka Onitsuka、Shigetoshi Takahashi

  DOI：10.1021/ol990377d

  日期：2000.2.1

  [GRAPHICS]Ruthenium complex catalyzed carbonylation of allenyl alcohols quantitatively gave cyclic carbonyl compounds, gamma- and delta-lactones, in which the hydroxy group of allenyl alcohols participated in the cyclization, A wide variety of allenyl alcohols, such as mono, di-, and trisubstituted alcohols, can be used in this reaction to produce 3- and 4-substituted gamma-lactones. Similarly, the cyclic carbonylation of 3,4-pentadien-1-ol 10a and 2-methyl-4,5-hexadien-2-ol 11a gave delta-lactones, 5,6-dihydro-3-methyl-2H-pyran-2-one 10b, and 5,6-dihydro-6,6-dimethyl-3-methyl-2H-pyran-2-one 11b, respectively, in a quantitative yield.
• Enzymatic halocyclization of allenic alcohols and carboxylates: a biocatalytic entry to functionalized O-heterocycles
  作者：J. Naapuri、J. D. Rolfes、J. Keil、C. Manzuna Sapu、J. Deska

  DOI：10.1039/c6gc01926a

  日期：——

  Chloroperoxidase from Caldariomyces fumago catalyzes the aerobic oxidative halocyclization of allenic alcohols and carboxylates yielding functionalized furan and pyran heterocycles as valuable synthetic scaffolds. Thanks to an oxidase-initiated redox cascade,...

  产自烟曲霉的氯过氧化物酶催化烯丙醇和羧酸的需氧氧化卤代环化反应，生成功能化的呋喃和吡喃杂环，作为有价值的合成支架。得益于氧化酶引发的氧化还原级联反应，...
• 3,3-Dimethylallenyllithium. Reaction with electrophiles leading to carbenoid, electron transfer, and nucleophilic processes
  作者：Xavier Creary

  DOI：10.1021/ja00465a035

  日期：1977.11