1-((1r,4r)-4-(tert-butyl)-1-hydroxycyclohexyl)ethan-1-one | 6555-58-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-((1r,4r)-4-(tert-butyl)-1-hydroxycyclohexyl)ethan-1-one
• 英文别名: 1β-Acetyl-4β-t-butyl-1α-cyclohexanol；1-ref-Acetyl-4-cis-tert.-butyl-cyclohexanol-(1-trans)；trans-1-Acetyl-4-t-butyl-cyclohexanol
• CAS: 6555-58-4
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: JQXZOQVVNKGQHT-UMSPYCQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-((1r,4r)-4-(tert-butyl)-1-hydroxycyclohexyl)ethan-1-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-tert-Butyl-1-(1-hydroxy-ethyl)-cyclohexanol
  参考文献：
  名称：

  酮与O-甲基肟的电还原分子间偶联。合成2-氨基醇的便捷途径

  摘要：

  酮与O-甲基肟的电还原得到分子间偶联的产物2-甲氧基氨基醇，该产物容易还原为2-氨基醇。

  DOI：

  10.1016/s0040-4039(00)79486-x
• 作为产物：
  描述：

  4-叔丁基环己酮 、 乙腈 在 四乙基对甲苯磺酸铵 作用下， 以 异丙醇 为溶剂， 以15%的产率得到1-(Cyanmethyl)-1-hydroxy-4-tert.-butylcyclohexan
  参考文献：
  名称：

  Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.

  摘要：

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00052a036

文献信息

• Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, and Nitrones. A Convenient Route to Synthesis of .beta.-Amino Alcohol
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Ayuko Yamanami、Ryoji Nomura

  DOI：10.1021/jo00086a023

  日期：1994.4

  The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode. The product, beta-methoxyamino alcohol was easily converted to beta-amino alcohol by simple reduction. A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime. The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction. Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.