2-cyclohexenylbutane-1,4-diol | 79828-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-cyclohexenylbutane-1,4-diol
• 英文别名: 2-(cyclohexen-1-yl)butane-1,4-diol
• CAS: 79828-36-7
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: RGBNTKUCKZGATQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-cyclohexenylbutane-1,4-diol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 6-(4-bromophenyl)octahydro-2H-cyclopenta[c]furo[2,3-d]pyran
  参考文献：
  名称：

  Domino Strategy for the Stereoselective Construction of Angularly Fused Tricyclic Ethers

  摘要：

  A stereoselective synthesis of decahydrofuro [3,2-d]-isochromene derivatives has been achieved by the condensation of cyclohexenylbutane-1,4-diol with aldehydes in the presence of a stochiometric amount of BF3 center dot OEt2 in dichloromethane at -78 degrees C. Similarly, the condensation of 2-cyclopentenylbutan-1,4-diol with aldehydes provides the corresponding octahydro-2H-cyclopenta[c]furo-[2,3-d]pyran derivatives in good yields with high diastereoseleetivity. It is an,elegant strategy for the quick construction of tricyclic architectures with four contiguous stereogenic centers in a single step. These tricyclic frameworks are the integral part of numerous natural products.

  DOI：

  10.1021/acs.joc.5b02241
• 作为产物：
  描述：

  环己酮 在 lithium aluminium tetrahydride 、 乙醇 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 25.33h， 生成 2-cyclohexenylbutane-1,4-diol
  参考文献：
  名称：

  Domino Strategy for the Stereoselective Construction of Angularly Fused Tricyclic Ethers

  摘要：

  A stereoselective synthesis of decahydrofuro [3,2-d]-isochromene derivatives has been achieved by the condensation of cyclohexenylbutane-1,4-diol with aldehydes in the presence of a stochiometric amount of BF3 center dot OEt2 in dichloromethane at -78 degrees C. Similarly, the condensation of 2-cyclopentenylbutan-1,4-diol with aldehydes provides the corresponding octahydro-2H-cyclopenta[c]furo-[2,3-d]pyran derivatives in good yields with high diastereoseleetivity. It is an,elegant strategy for the quick construction of tricyclic architectures with four contiguous stereogenic centers in a single step. These tricyclic frameworks are the integral part of numerous natural products.

  DOI：

  10.1021/acs.joc.5b02241

文献信息

• Dimethylaluminum chloride catalyzed ene reactions of aldehydes
  作者：Barry B. Snider、David J. Rodini、Thomas C. Kirk、Robert Cordova

  DOI：10.1021/ja00366a031

  日期：1982.1
• SNIDER, B. B.;RODINI, D. J.;KIRK, T. C.;CORDOVA, R., J. AMER. CHEM. SOC., 1982, 104, N 2, 555-563
  作者：SNIDER, B. B.、RODINI, D. J.、KIRK, T. C.、CORDOVA, R.

  DOI：——

  日期：——