Ethyl 4-(3,3-dimethyl-2-oxocyclohexyl)butyrate | 160481-88-9

• 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: Ethyl 4-(3,3-dimethyl-2-oxocyclohexyl)butyrate
• 英文别名: Ethyl 4-(3,3-dimethyl-2-oxocyclohexyl)butanoate
• CAS: 160481-88-9
• 化学式: C₁₄H₂₄O₃
• 分子量: 240.343
• InChiKey: LORXWRRFLIYGAU-UHFFFAOYSA-N

物化性质

• 沸点：
  314.9±15.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(3,3-dimethyl-2-oxocyclohexyl)butyrate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 1,1-Dimethyl-1,2,3,4,6,7,8,9-octahydro-5H-benzocyclohepten-8-one
  参考文献：
  名称：

  Retinoids and Related Compounds. 17. Conformational Study of Retinochrome Chromophore: Synthesis of 8,18-Ethanoretinal and a New Retinochrome Analog

  摘要：

  In order to investigate the chromophore conformation around the trimethylcyclohexene ring in retinochrome, (all-E)-8,18-ethanoretinal (2), in which C-8 and C-18 positions of retinal 1 was connected by an ethylene group, was synthesized via the Dieckmann condensation of diester 6 from 2,2-dimethylcyclohexanone 7. This analog 2 was incorporated into aporetinochrome, forming a pigment with lambda(max) at 498 nm. Its opsin shift (2200 cm(-1)) is of the same order of magnitude as that of native retinochrome (2400 cm(-1)), suggesting that the conformations of both chromophores are fairly similar in the protein. In addition, MMX calculations indicate that the torsional angle around the 6-7 single bond in retinochrome might correspond to the allowable torsional angle in 8,18-ethanoretinal (2).

  DOI：

  10.1021/jo00102a015
• 作为产物：
  描述：

  2,2-二甲基环己酮 在 sodium hydride 、 magnesium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 6.0h， 生成 Ethyl 4-(3,3-dimethyl-2-oxocyclohexyl)butyrate
  参考文献：
  名称：

  Synthesis of 818-ethanoretinal and its interaction with apo-retinochrome

  摘要：

  All-(E)-8,18-ethanoretinal was synthesized from 2,2-dimethylcyclohexanone, and its binding experiment with apo-retinochrome afforded the new retinochrome analog, whose opsin shift exhibited fairly similar to that of the natural retinochrome.

  DOI：

  10.1016/s0040-4039(00)77494-6

文献信息

• An Improved Synthesis of Benzocycloalkanone Derivatives
  作者：Akimori Wada、Kyoko Sawada、Naomi Ono、Masayoshi Ito

  DOI：10.1248/cpb.52.132

  日期：——

  A convenient and improved annulation method for the synthesis of bicyclic ketones was developed. A 2,2-dimethyl-6-(2-phenylsulfonyl)ethylcyclohexanone was converted into a sulfonylester by the addition of ethyl acetate and subsequent dehydration. A Dieckmann type condensation of the sulfonylester followed by desulfonylation afforded the 8,8-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalene-2-one in good

  开发了一种方便且改进的合成双环酮的方法。通过加入乙酸乙酯并随后脱水，将2，2-二甲基-6-（2-苯基磺酰基）乙基环己酮转化为磺酰基酯。磺酰基酯的狄克曼型缩合，然后进行磺酰化以良好的产率得到8,8-二甲基-1,2,3,4,5,6,7,8-八氢萘-2-酮。该环状方法也适用于苯并环辛酮衍生物的合成。