(RS)-4-methoxychroman-8-ol | 600708-83-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (RS)-4-methoxychroman-8-ol
• 英文别名: 4-methoxy-3,4-dihydro-2H-chromen-8-ol
• CAS: 600708-83-6
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: CZNJPCHEIBHDPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氟脲嘧啶 、 (RS)-4-methoxychroman-8-ol 在 三甲基氯硅烷 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 以44%的产率得到(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-hydroxyphenoxy)acetaldehyde dimethyl acetal 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 7.0h， 以51%的产率得到(RS)-4-methoxychroman-8-ol
  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