1,2-(benzylidenedioxy)-3,5-cyclohexadiene | 199874-57-2

• 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: 1,2-(benzylidenedioxy)-3,5-cyclohexadiene
• 英文别名: (3aR,7aS)-2-phenyl-3a,7a-dihydro-1,3-benzodioxole
• CAS: 199874-57-2
• 化学式: C₁₃H₁₂O₂
• 分子量: 200.237
• InChiKey: AQFOPOKLCKZTAJ-FUNVUKJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-(benzylidenedioxy)-3,5-cyclohexadiene 在 potassium tert-butylate 、 magnesium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 41.0h， 生成 1,4-乙烯桥-1,4-二氢萘
  参考文献：
  名称：

  New Syntheses of Benzobarrelenes

  摘要：

  New syntheses of both substituted and unsubstituted benzobarrelenes are described. Treatment of 3,5-cyclohexadiene-cis-1,2-diol with benzaldehyde dimethyl acetal in the presence of a catalytic amount of p-toluenesulfonic acid gave 1,2-(benzylidenedioxy)-3,5-cyclohexadiene (2). Addition of benzynes to 2 provided 3 and 4. Treatment of 3 and 4 with excess LDA and potassium tert-butoxide afforded benzobarrelenes 1 and 5 in good yields.

  DOI：

  10.1021/jo00085a024
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 cis-1,2-dihydrocatechol 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1,2-(benzylidenedioxy)-3,5-cyclohexadiene
  参考文献：
  名称：

  New Syntheses of Benzobarrelenes

  摘要：

  New syntheses of both substituted and unsubstituted benzobarrelenes are described. Treatment of 3,5-cyclohexadiene-cis-1,2-diol with benzaldehyde dimethyl acetal in the presence of a catalytic amount of p-toluenesulfonic acid gave 1,2-(benzylidenedioxy)-3,5-cyclohexadiene (2). Addition of benzynes to 2 provided 3 and 4. Treatment of 3 and 4 with excess LDA and potassium tert-butoxide afforded benzobarrelenes 1 and 5 in good yields.

  DOI：

  10.1021/jo00085a024

文献信息

• Synthesis of Substituted Bicyclo[2.2.2]octatrienes
  作者：Michael W. Wagaman、Erika Bellmann、Michèle Cucullu、Robert H. Grubbs

  DOI：10.1021/jo971039y

  日期：1997.12.1

  An efficient route to bicyclo[2.2.2]octatriene, barrelene, and substituted versions of this molecule has been developed starting from the benzene equivalent cis-3,5-cyclohexadiene-1,2-diol. Following the Diels-Alder reaction of this molecule with an activated acetylene, conversion of the diol to the final olefin was accomplished through formation of a thiocarbonate intermediate and subsequent reaction with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine (DPD). The synthesis developed allows a variety of barrelenes to be prepared in as few as three steps from commercially available starting materials.
• New Syntheses of Benzobarrelenes
  作者：Lin Pu、Robert H. Grubbs

  DOI：10.1021/jo00085a024

  日期：1994.3

  New syntheses of both substituted and unsubstituted benzobarrelenes are described. Treatment of 3,5-cyclohexadiene-cis-1,2-diol with benzaldehyde dimethyl acetal in the presence of a catalytic amount of p-toluenesulfonic acid gave 1,2-(benzylidenedioxy)-3,5-cyclohexadiene (2). Addition of benzynes to 2 provided 3 and 4. Treatment of 3 and 4 with excess LDA and potassium tert-butoxide afforded benzobarrelenes 1 and 5 in good yields.