1,2,3,4-tetrahydro-2,3-(benzylidenedioxy)-1,4-ethenonaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-2,3-(benzylidenedioxy)-1,4-ethenonaphthalene
• 英文别名: (1S,8R,9R,13S)-11-phenyl-10,12-dioxatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,14-tetraene
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: AIDFBJNCSZDGER-MKAJOQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  1,2,3,4-tetrahydro-2,3-(benzylidenedioxy)-1,4-ethenonaphthalene 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 以90%的产率得到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：

  cis-1,2-dihydrocatechol 在 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 1,2,3,4-tetrahydro-2,3-(benzylidenedioxy)-1,4-ethenonaphthalene
  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

• 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.