1-(1-Methoxypropadienyl)-cyclohexanol | 22082-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-Methoxypropadienyl)-cyclohexanol
• 英文别名: 1-(1-Methoxypropadienyl)cyclohexan-1-ol
• CAS: 22082-41-3
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: MOGQWTNJTFRANU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-Methoxypropadienyl)-cyclohexanol 在 硫酸 作用下， 生成 1-(1-羟基环己基)丙-2-烯-1-酮
  参考文献：
  名称：

  Hoff,S. et al., Recueil des Travaux Chimiques des Pays-Bas, 1968, vol. 87, p. 1179 - 1184

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲氧基-1,2-丙二烯 、 环己酮 在 正丁基锂 作用下， 生成 1-(1-Methoxypropadienyl)-cyclohexanol
  参考文献：
  名称：

  Ruthenium-Catalyzed Cyclic Carbonylation of Allenyl Alcohols. Selective Synthesis of γ- and δ-Lactones

  摘要：

  [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.

  DOI：

  10.1021/ol990377d

文献信息

• Mechanistic and synthetic aspects of intramolecular alkoxide–allene cyclizations
  作者：Philip Magnus、Pamela Albaugh-Robertson

  DOI：10.1039/c39840000804

  日期：——

  Intramolecular cyclization of the methoxyallene–alkoxide adducts (1a) proceeds along two different pathways via a methoxyallyl radical to give either a dihydrofuran, or vinyl epoxide, depending upon the steric environment of the redical anion.

  甲氧基烯丙基-醇盐加合物（1a）的分子内环化过程通过甲氧基烯丙基通过两种不同的途径进行，从而生成二氢呋喃或乙烯基环氧化合物，具体取决于红色阴离子的空间环境。
• 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.
• MAGNUS, PH.;ALBAUGH-ROBERTSON, P., J. CHEM. SOC. CHEM. COMMUN., 1984, N 12, 804-806
  作者：MAGNUS, PH.、ALBAUGH-ROBERTSON, P.

  DOI：——

  日期：——
• Hoff,S. et al., Recueil des Travaux Chimiques des Pays-Bas, 1968, vol. 87, p. 1179 - 1184
  作者：Hoff,S. et al.

  DOI：——

  日期：——
• 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.