2-(2-hydroxyphenoxy)ethyl-1,3-dioxolane | 600708-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-hydroxyphenoxy)ethyl-1,3-dioxolane
• 英文别名: 2-[2-(1,3-Dioxolan-2-yl)ethoxy]phenol；2-[2-(1,3-dioxolan-2-yl)ethoxy]phenol
• CAS: 600708-85-8
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: GADFADYILLSQEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  337.6±22.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyphenoxy)ethyl-1,3-dioxolane 在 三甲基氯硅烷 、 硫酸 、 三氟化硼乙醚 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 103.0h， 生成 (RS)-1-(8-hydroxychroman-4-yl)-5-fluorouracil
  参考文献：
  名称：

  Medium benzene-fused oxacycles with the 5-fluorouracil moiety: synthesis, antiproliferative activities and apoptosis induction in breast cancer cells

  摘要：

  On the basis of the increase in lipophilicity, novel benzannelated six- and seven-membered derivatives have been synthesized, starting from 2-hydroxybenzyl alcohols, 2-hydroxybenzaldehydes, and catechol. The X-ray structure of (RS)-1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil (5) is presented and compared with its conformational analysis at the semiempirical (AM1) and ab initio (6-31G*) levels and NOE effects. A good agreement between both experimental and theoretical data was found showing a chair conformation for the 2,3-dihydro-5H-1,4-dioxepin ring and an axial orientation of the 5-FU moiety on the C3 position. Compounds 5 and (RS)-1-(7methoxy-2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil (6) were found to be the most potent inhibitor of MCF-7 cells growth. (RS)1-(2,3-Dihydrobenzoxepin-2-yl)-5-fluorouracil (8) induced apoptosis up to 57.33% of cell population after 24 It. (C) 2003 Elsevier Science Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)00871-8
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 、 邻苯二酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以21%的产率得到2-(2-hydroxyphenoxy)ethyl-1,3-dioxolane
  参考文献：
  名称：

  Medium benzene-fused oxacycles with the 5-fluorouracil moiety: synthesis, antiproliferative activities and apoptosis induction in breast cancer cells

  摘要：

  On the basis of the increase in lipophilicity, novel benzannelated six- and seven-membered derivatives have been synthesized, starting from 2-hydroxybenzyl alcohols, 2-hydroxybenzaldehydes, and catechol. The X-ray structure of (RS)-1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil (5) is presented and compared with its conformational analysis at the semiempirical (AM1) and ab initio (6-31G*) levels and NOE effects. A good agreement between both experimental and theoretical data was found showing a chair conformation for the 2,3-dihydro-5H-1,4-dioxepin ring and an axial orientation of the 5-FU moiety on the C3 position. Compounds 5 and (RS)-1-(7methoxy-2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil (6) were found to be the most potent inhibitor of MCF-7 cells growth. (RS)1-(2,3-Dihydrobenzoxepin-2-yl)-5-fluorouracil (8) induced apoptosis up to 57.33% of cell population after 24 It. (C) 2003 Elsevier Science Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)00871-8

文献信息

• Medium benzene-fused oxacycles with the 5-fluorouracil moiety: synthesis, antiproliferative activities and apoptosis induction in breast cancer cells
  作者：Estrella Saniger、Joaquı́n M Campos、Antonio Entrena、Juan A Marchal、Inés Suárez、Antonia Aránega、Duane Choquesillo、Juán Niclós、Miguel Á Gallo、Antonio Espinosa

  DOI：10.1016/s0040-4020(03)00871-8

  日期：2003.7

  On the basis of the increase in lipophilicity, novel benzannelated six- and seven-membered derivatives have been synthesized, starting from 2-hydroxybenzyl alcohols, 2-hydroxybenzaldehydes, and catechol. The X-ray structure of (RS)-1-(2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil (5) is presented and compared with its conformational analysis at the semiempirical (AM1) and ab initio (6-31G*) levels and NOE effects. A good agreement between both experimental and theoretical data was found showing a chair conformation for the 2,3-dihydro-5H-1,4-dioxepin ring and an axial orientation of the 5-FU moiety on the C3 position. Compounds 5 and (RS)-1-(7methoxy-2,3-dihydro-5H-1,4-benzodioxepin-3-yl)-5-fluorouracil (6) were found to be the most potent inhibitor of MCF-7 cells growth. (RS)1-(2,3-Dihydrobenzoxepin-2-yl)-5-fluorouracil (8) induced apoptosis up to 57.33% of cell population after 24 It. (C) 2003 Elsevier Science Ltd. All fights reserved.