cis-1,2-dihydroxy-1,2-dihydrobenzocyclobutene | 70355-68-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: cis-1,2-dihydroxy-1,2-dihydrobenzocyclobutene
• 英文别名: cis-benzocyclobuten-1,2-diol；cis-7,8-Dihydroxy-bicyclo<4,2,0>octatrien-(1,3,5)；cis-1,2-Dihydroxy-benzocyclobuten；(7S,8R)-bicyclo[4.2.0]octa-1,3,5-triene-7,8-diol
• CAS: 70355-68-9；193472-43-4
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: HYAGFRZWXCUXRZ-OCAPTIKFSA-N

物化性质

• 沸点：
  293.5±40.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  cis-1,2-dihydroxy-1,2-dihydrobenzocyclobutene 、 乙酸酐 在 吡啶 作用下， 以83%的产率得到cis-1,2-diacetoxy-1,2-dihydrobenzocyclobutene
  参考文献：
  名称：

  Toluene dioxygenase-catalysed oxidation route to angular cis-monohydrodiols and other bioproducts from bacterial metabolism of 1,2-dihydrobenzocyclobutene and derivatives

  摘要：

  土壤细菌恶臭假单胞菌(Pseudomonas putida)的突变株(UV4)含有甲苯双加氧酶,已被用于代谢氧化1,2-二氢苯并环丁烯12以及相关的底物1,2-二氢苯并环丁烯-1-醇13和联苯烯33。从这些底物中分离得到的稳定的角向顺式单羟基二醇代谢物,(1R,2S)-二环[4.2.0]辛-3,5-二烯-1,2-二醇7,(1S,2S,8S)-二环[4.2.0]辛-3,5-二烯-1,2,8-三醇8和联苯烯-顺式-1,8b-二醇9,已经通过结构和立体化学进行了指认。其他顺式二醇代谢物的结构、对映体纯度和绝对构型,(2R,3S)-二环[4.2.0]辛-1(6),4-二烯-2,3-二醇14和顺式-1,2-二羟基-1,2-二氢苯并环丁烯16,以及通过1,2-二氢苯并环丁烯和1,2-二氢苯并环丁烯-1-醇获得的苄基氧化生物产物,1,2-二氢苯并环丁烯-1-醇13、1,2-二氢苯并环丁烯-1-酮15和2-羟基-1,2-二氢苯并环丁烯-1-酮17,已经借助手性固定相HPLC、NMR和CD光谱以及立体化学相关性进行了确定。X射线晶体学方法已被用于确定相应顺式二醇代谢物的二樟脑酸盐27(来自二醇7)、32(来自二醇9)和二MTPA酯29(来自二醇14)的绝对构型。已经研究了1,2-二氢苯并环丁烯12形成衍生生物产物的代谢序列。

  DOI：

  10.1039/a608071e
• 作为产物：
  描述：

  2-羟基苯并环丁烯酮 、 氢化铝锂 以6%的产率得到
  参考文献：
  名称：

  CARPINO L. A.; TSAO J.-H., J. ORG. CHEM. 1979 44 NO 14 2387-2391

  摘要：

  DOI：

文献信息

• Mechanophore-Linked Addition Polymers
  作者：Stephanie L. Potisek、Douglas A. Davis、Nancy R. Sottos、Scott R. White、Jeffrey S. Moore

  DOI：10.1021/ja076189x

  日期：2007.11.1

  The use of mechanical energy to increase reaction rates and alter the distribution of products has gained considerable interest of late. However, the discovery of new mechanophores (i.e., mechanochemically reactive units) is currently time-consuming, expensive, low-yielding, and a process that is not easily scaled to large quantities. Here we show that mechanophore-linked addition polymers are easily prepared using bifunctional initiators with a living radical polymerization method. The mechanophore is positioned close to the center of the polymer, where ultrasound-generated forces are the largest. Since these forces are strongly dependent on molecular weight, the use of controlled polymerization enables fine-tuning of the mechanical activity so that mechanophore reactions are initiated while minimizing chain scission. The approach is illustrated first with the synthesis and investigation of a 1,2-disubstituted benzocyclobutene mechanophore that is incorporated into the center of a polymethacrylate (PMA) chain. Selected molecular weights are probed using ultrasound to illustrate that the 4 pi electrocyclic ring opening of the benzocyclobutene link is stress-induced. To demonstrate the broad applicability of this method for mechanophore screening, we also report a new spiropyran-linked PMA that undergoes an ultrasound-induced 6 pi-electron electrocyclic ring opening. The straightforward synthesis of mechanophore-linked addition polymers presented here shows considerable promise for the investigation of new mechanophores and will lead to a greater understanding of mechanochemical reactivity within polymer systems.
• Bacterial oxidation of benzocyloalkenes to yield monol, diol and triol metabolites
  作者：Boyd Derek R.、Sharma Narain D.、Stevenson Paul J.、Chima Jagdeep、Gray David J.、Dalton Howard

  DOI：10.1016/s0040-4039(00)79405-6

  日期：1991.7