9,10-dihydro-9,10-dihydroxy-1,5-diiodoanthracene | 374621-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 9,10-dihydro-9,10-dihydroxy-1,5-diiodoanthracene
• 英文别名: 1,5-Diiodo-9,10-dihydroanthracene-9,10-diol
• CAS: 374621-36-0
• 化学式: C₁₄H₁₀I₂O₂
• 分子量: 464.041
• InChiKey: XHJJDFZLWCKHKO-UHFFFAOYSA-N

物化性质

• 沸点：
  496.5±45.0 °C(Predicted)
• 密度：
  2.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-9,10-dihydroxy-1,5-diiodoanthracene 在 苯肼 作用下， 以 溶剂黄146 为溶剂， 反应 7.0h， 以18%的产率得到1,5-diiodoanthracene
  参考文献：
  名称：

  Intramolecular Behaviors of Anthryldicarbenic Systems:  Dibenzo[b,f]pentalene and 1H,5H-Dicyclobuta[de,kl]anthracene

  摘要：

  9,10-Bis[methoxy(trimethylsilyl)methyl]anthracenes (24), synthesized from 9,10-dilithioanthracene (26) and bromomethoxytrimethylsilylmethane (27, 2 equiv), decompose (550-650 degreesC/10(-3) mmHg) carbenically to dibenzo[b,f]pentalene (28, > 48%). 9,10-Anthryldicarbenes 39 or their equivalents convert to pentalene 28 rather than di-peri-cyclobutanthracenes 30 and 31, benzobiphenylene 32, or extended rearrangement products 33-38. Formation of 28 from 24 raises questions with respect to the behavior of 1,3,4,6-cycloheptatetraenyl-1-carbenes 49, 2,4,5,7-cyclooctatetraenylidene 51, 2,5,7-cyclooetatriene-1,4-diylidene 52, 1,2,4,5,7-cyclooetapentaene 53, and bicyclo[4.1.0]heptatrienyl-1-carbenes 54 and to carbon-skeleton and hydrogen rearrangements of anthryldicarbenes 39 and/or their equivalents at various temperatures. 1,5-Bis [methoxy(trimethylsilyl)methyl] anthracenes (25), prepared from 1,5-diiodoanthracene (63) and methoxytrimethylsilylmethylzinc bromide (57,2 equiv) as catalyzed by PdCl2(PPh3)(2), yield the di-peri-carbenic reaction product 1H,5H-dicyclobuta[de,kl]-anthracene (30, > 40%) on pyrolysis at 550-650 degreesC/10(-3) mmHg. Proof of structure and various aspects of the mechanisms of formation of 30 are discussed.

  DOI：

  10.1021/jo010404p
• 作为产物：
  描述：

  1,5-diiodo-9,10-anthraquinone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 0.5h， 生成 9,10-dihydro-9,10-dihydroxy-1,5-diiodoanthracene
  参考文献：
  名称：

  Intramolecular Behaviors of Anthryldicarbenic Systems:  Dibenzo[b,f]pentalene and 1H,5H-Dicyclobuta[de,kl]anthracene

  摘要：

  9,10-Bis[methoxy(trimethylsilyl)methyl]anthracenes (24), synthesized from 9,10-dilithioanthracene (26) and bromomethoxytrimethylsilylmethane (27, 2 equiv), decompose (550-650 degreesC/10(-3) mmHg) carbenically to dibenzo[b,f]pentalene (28, > 48%). 9,10-Anthryldicarbenes 39 or their equivalents convert to pentalene 28 rather than di-peri-cyclobutanthracenes 30 and 31, benzobiphenylene 32, or extended rearrangement products 33-38. Formation of 28 from 24 raises questions with respect to the behavior of 1,3,4,6-cycloheptatetraenyl-1-carbenes 49, 2,4,5,7-cyclooctatetraenylidene 51, 2,5,7-cyclooetatriene-1,4-diylidene 52, 1,2,4,5,7-cyclooetapentaene 53, and bicyclo[4.1.0]heptatrienyl-1-carbenes 54 and to carbon-skeleton and hydrogen rearrangements of anthryldicarbenes 39 and/or their equivalents at various temperatures. 1,5-Bis [methoxy(trimethylsilyl)methyl] anthracenes (25), prepared from 1,5-diiodoanthracene (63) and methoxytrimethylsilylmethylzinc bromide (57,2 equiv) as catalyzed by PdCl2(PPh3)(2), yield the di-peri-carbenic reaction product 1H,5H-dicyclobuta[de,kl]-anthracene (30, > 40%) on pyrolysis at 550-650 degreesC/10(-3) mmHg. Proof of structure and various aspects of the mechanisms of formation of 30 are discussed.

  DOI：

  10.1021/jo010404p