1,2,3,4-tetrahydro-1,2-dimethylidenenaphthalene | 475579-30-7

• 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-1,2-dimethylidenenaphthalene
• 英文别名: 3,4-Dimethylidene-1,2-dihydronaphthalene
• CAS: 475579-30-7
• 化学式: C₁₂H₁₂
• 分子量: 156.227
• InChiKey: GZLORJZZRBCBJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-1,2-dimethylidenenaphthalene 在 二氧化硫 作用下， 反应 12.0h， 以37%的产率得到1,3,4,5-tetrahydronaphtho[1,2-c]thiophene 2,2-dioxide
  参考文献：
  名称：

  Synthesis of 1,2,3,4-Tetrahydro-1,2-dimethylidenenaphthalene: A Reactive s-cis-Butadiene Undergoing Highly Chemo- and Regioselective Cyclodimerization

  摘要：

  1,2,3,4-Tetrahydro-1,2-dimethylidenenaphtlhalene 11 has been derived in three steps from tetralone. In the condensed state and at - 80degrees, it undergoes a highly chemo- and regioselective cyclodimerization to give 3.3',4,4'-tetrahydro-2-methylidenespiro[naphthalene-1 (2H).2(1H)-phenanthrene] (14). the structure of which has been established by single-crystal X-ray-diffraction analysis. Dimer 14 undergoes cycloreversion to diene 11 under flash-pyrolysis conditions. The reaction of diene 11 with SO, occurs without acid promoter at -80degrees and gives it mixture of (+/-)-1,4,5.6-tetrahydronaphth[1,2-d][1,2]oxathin 2-oxide (23 a single sultine). 1.3.4,5-tetrahydronaphtho[1.2-c]thiophene 2,2-dioxide (25), and dimer 14. The high reactivity of diene 1 in its Diels-Alder cyclodimerization and its highly regioselective hetero-Diels-A Ider addition with SO, can be interpreted in terms of the formation of relatively stable diradical intermediates or by concerted processes with transition states that can be represented as diradicaloids.

  DOI：

  10.1002/1522-2675(200205)85:5<1390::aid-hlca1390>3.0.co;2-7
• 作为产物：
  描述：

  3,3,4,4'-tetrahydro-2-methylidenespiro[naphthalene-1(2H),2'(1'H)-phenanthrene] 800.0 ℃ 、10.0 Pa 条件下， 以25%的产率得到1,2,3,4-tetrahydro-1,2-dimethylidenenaphthalene
  参考文献：
  名称：

  Synthesis of 1,2,3,4-Tetrahydro-1,2-dimethylidenenaphthalene: A Reactive s-cis-Butadiene Undergoing Highly Chemo- and Regioselective Cyclodimerization

  摘要：

  1,2,3,4-Tetrahydro-1,2-dimethylidenenaphtlhalene 11 has been derived in three steps from tetralone. In the condensed state and at - 80degrees, it undergoes a highly chemo- and regioselective cyclodimerization to give 3.3',4,4'-tetrahydro-2-methylidenespiro[naphthalene-1 (2H).2(1H)-phenanthrene] (14). the structure of which has been established by single-crystal X-ray-diffraction analysis. Dimer 14 undergoes cycloreversion to diene 11 under flash-pyrolysis conditions. The reaction of diene 11 with SO, occurs without acid promoter at -80degrees and gives it mixture of (+/-)-1,4,5.6-tetrahydronaphth[1,2-d][1,2]oxathin 2-oxide (23 a single sultine). 1.3.4,5-tetrahydronaphtho[1.2-c]thiophene 2,2-dioxide (25), and dimer 14. The high reactivity of diene 1 in its Diels-Alder cyclodimerization and its highly regioselective hetero-Diels-A Ider addition with SO, can be interpreted in terms of the formation of relatively stable diradical intermediates or by concerted processes with transition states that can be represented as diradicaloids.

  DOI：

  10.1002/1522-2675(200205)85:5<1390::aid-hlca1390>3.0.co;2-7

文献信息

• Synthesis of 1,2,3,4-Tetrahydro-1,2-dimethylidenenaphthalene: A Reactive s-cis-Butadiene Undergoing Highly Chemo- and Regioselective Cyclodimerization
  作者：Elena Roversi、Pierre Vogel、Kurt Schenk

  DOI：10.1002/1522-2675(200205)85:5<1390::aid-hlca1390>3.0.co;2-7

  日期：2002.5

  1,2,3,4-Tetrahydro-1,2-dimethylidenenaphtlhalene 11 has been derived in three steps from tetralone. In the condensed state and at - 80degrees, it undergoes a highly chemo- and regioselective cyclodimerization to give 3.3',4,4'-tetrahydro-2-methylidenespiro[naphthalene-1 (2H).2(1H)-phenanthrene] (14). the structure of which has been established by single-crystal X-ray-diffraction analysis. Dimer 14 undergoes cycloreversion to diene 11 under flash-pyrolysis conditions. The reaction of diene 11 with SO, occurs without acid promoter at -80degrees and gives it mixture of (+/-)-1,4,5.6-tetrahydronaphth[1,2-d][1,2]oxathin 2-oxide (23 a single sultine). 1.3.4,5-tetrahydronaphtho[1.2-c]thiophene 2,2-dioxide (25), and dimer 14. The high reactivity of diene 1 in its Diels-Alder cyclodimerization and its highly regioselective hetero-Diels-A Ider addition with SO, can be interpreted in terms of the formation of relatively stable diradical intermediates or by concerted processes with transition states that can be represented as diradicaloids.