(RS)-2-methoxy-2,3-dihydrobenzoxepin | 600708-82-5

• 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)-2-methoxy-2,3-dihydrobenzoxepin
• 英文别名: 2-Methoxy-2,3-dihydro-1-benzoxepine
• CAS: 600708-82-5
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: HZHDPZOETLDSSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氟脲嘧啶 、 (RS)-2-methoxy-2,3-dihydrobenzoxepin 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10%的产率得到(RS)-1-(2,3-dihydrobenzoxepin-2-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：

  (Z)-4-(2-hydroxyphenyl)-3-butenal dimethyl acetal 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 7.0h， 以34%的产率得到(RS)-2-methoxy-2,3-dihydrobenzoxepin
  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

• Cyclization of 2-Ethynylphenyl Vinyl Ether Catalyzed by a Ruthenium Complex: Mechanism of Catalytic Cyclization and Stoichiometric Cycloisomerization
  作者：Chi-Ren Chen、Ying-Xuan Lai、Rong-Yu Wu、Yi-Hung Liu、Ying-Chih Lin

  DOI：10.1002/cctc.201600428

  日期：2016.7.6

  reactions and new stoichiometric skeletal rearrangement cycloisomerizations of 2‐ethynylphenyl vinyl ethers containing methyl substituents on the vinyl groups by using [Ru]Cl [Ru]=Cp(PPh3)2Ru, Cp=η5‐cyclopentadienyl} were observed in MeOH and CH2Cl2, respectively. In MeOH, the catalytic cyclization of three different enynes gave the corresponding benzoxepine derivatives in high yields in each case. Interestingly

  通过使用催化环化反应和含对乙烯基甲基取代基的2-乙炔基苯基乙烯基醚新化学计量骨架重排cycloisomerizations的[Ru]氯[茹] = CP（PPH 3）2的Ru中，CP =η 5 -环戊二烯基}观察分别在MeOH和CH 2 Cl 2中。在甲醇中，三种不同的炔烃的催化环化在每种情况下均以高收率得到了相应的苯并西平衍生物。有趣的是，在RuCl与烯炔的化学计量反应中，在CH 2 Cl 2中观察到了两个前所未有的烯炔重排。。甲基中的乙烯基单元的存在下，在选择偏二配体，即，在Ru =Cα或C的双键中的一个起关键作用α =Cβ键，对于[2 + 2]环加成在环异构化过程。通过单晶X射线衍射分析确定的结构以及各种同位素研究证实了所提出的机理。