3-benzyloxymethyl-cyclohex-2-enone | 97997-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzyloxymethyl-cyclohex-2-enone
• 英文别名: 3-(phenylmethoxymethyl)cyclohex-2-en-1-one
• CAS: 97997-32-5
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: NOKBXTPSXHDVMT-UHFFFAOYSA-N

物化性质

• 沸点：
  340.1±31.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  烯丙基三丁基锡 、 3-benzyloxymethyl-cyclohex-2-enone 在 五氯化钽 、 三氟甲磺酸三甲基硅酯 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 51.0h， 以60%的产率得到3-allyl-3((benzyloxy)methyl)-cyclohexan-1-one
  参考文献：
  名称：

  Asymmetric baker’s yeast reductions of bridgehead-substituted bicyclo[2.2.2]octane-2,6-dione derivatives followed by conversion into catalytically active BODOLs for the diethylzinc addition to benzaldehyde

  摘要：

  4-Substituted bicyclo[2.2.2]octane-2,6-diones have been synthesized and tested as substrates in the enantioselective reduction with baker's yeast to give the corresponding hydroxy ketones. It was found that the derivative bearing a TIPSO group at the 4-position was not reduced at all while that with a TBDMSO group gave 87% yield and 46% ee. Other 4-oxy functionalized derivatives were reduced with varying yields (36-87%) and ees (10-82%). The best result was obtained for the 4-Oallyl derivative (80% yield, 82% ee). The hydroxy ketones carrying the benzyloxy and allyloxy groups at the 4-position were converted into the corresponding BODOLs, which were tested as catalysts in the diethylzinc addition to benzaldehyde. In this reaction the ees were 90% and 89%, respectively, which showed that BODOLs substituted at the 4-position are essentially as good catalysts in this reaction as those bearing a hydrogen. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.003
• 作为产物：
  描述：

  1-(phenylmethoxymethyl)cyclohex-2-en-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以0.17 g的产率得到3-benzyloxymethyl-cyclohex-2-enone
  参考文献：
  名称：

  Asymmetric baker’s yeast reductions of bridgehead-substituted bicyclo[2.2.2]octane-2,6-dione derivatives followed by conversion into catalytically active BODOLs for the diethylzinc addition to benzaldehyde

  摘要：

  4-Substituted bicyclo[2.2.2]octane-2,6-diones have been synthesized and tested as substrates in the enantioselective reduction with baker's yeast to give the corresponding hydroxy ketones. It was found that the derivative bearing a TIPSO group at the 4-position was not reduced at all while that with a TBDMSO group gave 87% yield and 46% ee. Other 4-oxy functionalized derivatives were reduced with varying yields (36-87%) and ees (10-82%). The best result was obtained for the 4-Oallyl derivative (80% yield, 82% ee). The hydroxy ketones carrying the benzyloxy and allyloxy groups at the 4-position were converted into the corresponding BODOLs, which were tested as catalysts in the diethylzinc addition to benzaldehyde. In this reaction the ees were 90% and 89%, respectively, which showed that BODOLs substituted at the 4-position are essentially as good catalysts in this reaction as those bearing a hydrogen. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.003

文献信息

• Rh(I)-Catalyzed [5 + 1] Cycloaddition of Vinylcyclopropanes and CO for the Synthesis of α,β- and β,γ-Cyclohexenones
  作者：Guo-Jie Jiang、Xu-Fei Fu、Qian Li、Zhi-Xiang Yu

  DOI：10.1021/ol2031526

  日期：2012.2.3

  A cationic Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropanes and CO has been developed, affording either beta,gamma-cyclohexenones as major products or alpha,beta-cyclohexenones exclusively, under different reaction conditions.
• A general method for the preparation of .gamma.-substituted cyclohexenals and cycloheptenals
  作者：Todd K. Jones、Scott E. Denmark

  DOI：10.1021/jo00221a015

  日期：1985.10