5,5-dimethyl-3-(1-hydroxycyclohexane-1-yl)-2-cyclohexen-1-one | 81036-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-dimethyl-3-(1-hydroxycyclohexane-1-yl)-2-cyclohexen-1-one
• 英文别名: 3-(1-hydroxycyclohexyl)-5,5-dimethyl-2-cyclohexen-1-one；3-(1-hydroxycyclohexyl)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 81036-93-3
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: BATFAYQDKHBPMY-UHFFFAOYSA-N

物化性质

• 熔点：
  54-55 °C
• 沸点：
  349.1±41.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5,5-二甲基-3-溴环己-2-烯酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 5,5-dimethyl-3-(1-hydroxycyclohexane-1-yl)-2-cyclohexen-1-one
  参考文献：
  名称：

  An efficient and simple β-acylvinyl anion equivalent for cyclohexenones

  摘要：

  DOI：

  10.1016/s0040-4039(01)82108-0

文献信息

• Preparation and reactivity of functionalized alkenyl-zinc, -copper, and -chromium organometallics
  作者：Paul Knochel、C. Janakiram Rao

  DOI：10.1016/s0040-4020(01)80504-4

  日期：1993.1

  Beta-halogeno-alpha,beta-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45-degrees-C, 1-4h). These functionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97% yield. The addition of a THF solution of CuCN.2LiCl to 2a affords the corresponding organocopper derivatives 2b which react with electrophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfunctional unsaturated carbonyl compounds in 71-95% yield. The insertion of chromium (II) chloride to beta-iodo and to some beta-(p-tosyl)enones in DMF furnishes new functionalized chromium (III) organometallics 2c which react with aldehydes providing gamma-hydroxy unsaturated carbonyl derivatives in 40-91% yield. The synthetic scope and the limitations of this methodology are discussed.
• An efficient and simple β-acylvinyl anion equivalent for cyclohexenones
  作者：Chuan Shih、John S. Swenton

  DOI：10.1016/s0040-4039(01)82108-0

  日期：——
• SHIH, CHUAN;SWENTON, J. S., J. ORG. CHEM., 1982, 47, N 15, 2825-2832
  作者：SHIH, CHUAN、SWENTON, J. S.

  DOI：——

  日期：——
• Use of protected .beta.-bromocyclopentenones and .beta.-bromocyclohexenones as .beta.-acylvinyl anion equivalents
  作者：Chuan Shih、John S. Swenton

  DOI：10.1021/jo00136a001

  日期：1982.7