1,1-二甲氧基-3-甲基环己烷 | 18349-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1-二甲氧基-3-甲基环己烷
• 英文名称: 3-methyl-cyclohexanone dimethyl acetal
• 英文别名: 3-Methylcyclohexanone dimethyl acetal；3-methylcyclohexanone dimethyl ketal；3-Methyl-cyclohexanon-dimethylacetal；3-Methyl-cyclohexanon-dimethylketal；1,1-Dimethoxy-3-methyl-cyclohexan；3-Methyl-1,1-dimethoxy-cyclohexan；1,1-Dimethoxy-3-methylcyclohexane
• CAS: 18349-16-1
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: ITBKAZNVWBGZPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2911000000

反应信息

• 作为反应物：
  描述：

  1,1-二甲氧基-3-甲基环己烷 在 三氟化硼乙醚 、 potassium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 [1-(1-methoxy-3-methylcyclohexyl)-2-methylidenecyclobutyl]oxy-trimethylsilane
  参考文献：
  名称：

  Ring expansion and cleavage of succinoin derivatives. Geminal acylation, reductive succinoylation, and stereoselective spiro annelation methods

  摘要：

  DOI：

  10.1021/ja00318a035
• 作为产物：
  描述：

  甲醇 、 3-甲基环己酮 在 Ce⁽³⁺⁾-mont 作用下， 反应 0.5h， 以95%的产率得到1,1-二甲氧基-3-甲基环己烷
  参考文献：
  名称：

  Ce3+-Exchanged Montmorillonite (Ce3+-Mont) as a Useful Substrate-Selective Acetalization Catalyst

  摘要：

  The acetalization of carbonyl compounds with methanol was investigated in the presence of a cation-exchanged montmorillonite (M(n+)-mont; M(n+) = Ce3+, Zr4+, Fe3+, Al3+, Zn2+, Hf, and Na+). Ce3+-mont was found to be the most effective catalyst for substrate-selective acetalization. Cyclohexanones, benzaldehydes, and acid-sensitive 2-furancarboxaldehyde were converted nearly quantitatively to the corresponding acetals in methanol at 25 degrees C in the presence of Ce3+-mont. The substrates were activated by a Lewis acidic Ce3+ cation in the interlayer space on the order of 1 kJ mol(-1) as measured by FT-IR. The turnover number was estimated to be up to 2.6 x 10(3) based on the number of active acid sites in Ce3+-mont.

  DOI：

  10.1021/jo00118a021

文献信息

• Remarkable equatorial selectivity in the aldol coupling between enol silyl ethers and cyclohexanone acetals
  作者：Eiichi Nakamura、Yoshiaki Horiguchi、Jun-ichi Shimada、Isao Kuwajima

  DOI：10.1039/c39830000796

  日期：——

  Lewis acid-catalysed aldol coupling of enol silyl ethers and substituted cyclohexanone acetals shows a markedly higher ratio of equatorial attack than the reaction of the parent ketones.

  路易斯酸催化的烯醇甲硅烷基醚和取代的环己酮缩醛的醛醇缩合反应显示出比母体酮的反应明显更高的赤道侵蚀率。
• Ce3+-Exchanged Montmorillonite (Ce3+-Mont) as a Useful Substrate-Selective Acetalization Catalyst
  作者：Jun-ichi Tateiwa、Hiroki Horiuchi、Sakae Uemura

  DOI：10.1021/jo00118a021

  日期：1995.6

  The acetalization of carbonyl compounds with methanol was investigated in the presence of a cation-exchanged montmorillonite (M(n+)-mont; M(n+) = Ce3+, Zr4+, Fe3+, Al3+, Zn2+, Hf, and Na+). Ce3+-mont was found to be the most effective catalyst for substrate-selective acetalization. Cyclohexanones, benzaldehydes, and acid-sensitive 2-furancarboxaldehyde were converted nearly quantitatively to the corresponding acetals in methanol at 25 degrees C in the presence of Ce3+-mont. The substrates were activated by a Lewis acidic Ce3+ cation in the interlayer space on the order of 1 kJ mol(-1) as measured by FT-IR. The turnover number was estimated to be up to 2.6 x 10(3) based on the number of active acid sites in Ce3+-mont.
• SHIMADA, J. -ICHI;HASHIMOTO, KOICHI;KIM, BYEANG, HYEAN;NAKAMURA, EIICHI;K+, J. AMER. CHEM. SOC., 1984, 106, N 6, 1759-1773
  作者：SHIMADA, J. -ICHI、HASHIMOTO, KOICHI、KIM, BYEANG, HYEAN、NAKAMURA, EIICHI、K+

  DOI：——

  日期：——
• Ring expansion and cleavage of succinoin derivatives. Geminal acylation, reductive succinoylation, and stereoselective spiro annelation methods
  作者：Junichi Shimada、Koichi Hashimoto、Byeang Hyean Kim、Eiichi Nakamura、Isao Kuwajima

  DOI：10.1021/ja00318a035

  日期：1984.3
• Mild acetalisation of mono and dicarbonyl compounds catalysed by titanium tetrachloride. Facile synthesis of β-keto enol ethers
  作者：Angelo Clerici、Nadia Pastori、Ombretta Porta

  DOI：10.1016/s0040-4020(00)01001-2

  日期：2001.1

  The use of TiCl4, as a catalyst for the acetalisation, at room temperature, of carbonyl compounds is reported. Cyclic ketones and cyclic 1,4-diketones easily afford dimethyl acetals, but cyclic 1,3-diketones give beta -keto enol ethers. Additionally, aryl ketones and acyclic ketones failed to react. beta -keto aldehydes can be monoprotected either as beta -keto enol ethers or beta -keto dimethyl acetals depending on the reaction time and catalyst amount. Some mechanistic features are accounted for. (C) 2000 Elsevier Science Ltd. All rights reserved.