3,3-diethyl-1,2,3,8-tetrahydroazulen-1-one | 904368-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-diethyl-1,2,3,8-tetrahydroazulen-1-one
• CAS: 904368-93-0
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: REAVQWHANSIAEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,3-diethyl-1,2,3,8-tetrahydroazulen-1-one 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1,1-diethyl-1,4-dihydroazulene
  参考文献：
  名称：

  Synthesis and stability of 1,1-dialkyl-1H-azulenium cations

  摘要：

  Starting from trimethylsilyl enol ether of 1-acetyl-1,3,5-cycloheptatriene, the title 1,1-dimethyl-, 1,1-diethyl-, and 1,1-dipropyl-1H-azulenium cations 6-8 were synthesized in five steps. The order of pK(R)+ values of these cations was found to be 7 > 8 > 6. A comparison of the values between 1, 1-dialkyl- and 1, 1-spiroalkylated 1H-azulenium cations with the same number of carbon atoms at the I-position provided the results of 7 > 1 and 8 < 3. The cation 8 shows a relatively lower pKR+ value to those of 3 and 7 probably due to its slightly bulkier propyl groups from which solvation stabilization of 8 under the conditions suffers. An intermolecular charge-transfer interaction between the cations and dibenzo-24-crown-8 was also studied. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.084
• 作为产物：
  描述：

  1-Cyclohepta-1,3,5-trienyl-3-ethyl-3-hydroxy-pentan-1-one 在 甲酸 、 磷酸 作用下， 反应 4.0h， 以58%的产率得到3,3-diethyl-1,2,3,8-tetrahydroazulen-1-one
  参考文献：
  名称：

  Synthesis and stability of 1,1-dialkyl-1H-azulenium cations

  摘要：

  Starting from trimethylsilyl enol ether of 1-acetyl-1,3,5-cycloheptatriene, the title 1,1-dimethyl-, 1,1-diethyl-, and 1,1-dipropyl-1H-azulenium cations 6-8 were synthesized in five steps. The order of pK(R)+ values of these cations was found to be 7 > 8 > 6. A comparison of the values between 1, 1-dialkyl- and 1, 1-spiroalkylated 1H-azulenium cations with the same number of carbon atoms at the I-position provided the results of 7 > 1 and 8 < 3. The cation 8 shows a relatively lower pKR+ value to those of 3 and 7 probably due to its slightly bulkier propyl groups from which solvation stabilization of 8 under the conditions suffers. An intermolecular charge-transfer interaction between the cations and dibenzo-24-crown-8 was also studied. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.084

文献信息

• Synthesis and stability of 1,1-dialkyl-1H-azulenium cations
  作者：Mitsunori Oda、Nobue Nakajima、Nguyen Chung Thanh、Takanori Kajioka、Shigeyasu Kuroda

  DOI：10.1016/j.tet.2006.05.084

  日期：2006.8

  Starting from trimethylsilyl enol ether of 1-acetyl-1,3,5-cycloheptatriene, the title 1,1-dimethyl-, 1,1-diethyl-, and 1,1-dipropyl-1H-azulenium cations 6-8 were synthesized in five steps. The order of pK(R)+ values of these cations was found to be 7 > 8 > 6. A comparison of the values between 1, 1-dialkyl- and 1, 1-spiroalkylated 1H-azulenium cations with the same number of carbon atoms at the I-position provided the results of 7 > 1 and 8 < 3. The cation 8 shows a relatively lower pKR+ value to those of 3 and 7 probably due to its slightly bulkier propyl groups from which solvation stabilization of 8 under the conditions suffers. An intermolecular charge-transfer interaction between the cations and dibenzo-24-crown-8 was also studied. (c) 2006 Elsevier Ltd. All rights reserved.