p-methoxybenzyl 2,2-difluorovinyl ether | 446867-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: p-methoxybenzyl 2,2-difluorovinyl ether
• 英文别名: 1-(2,2-Difluoroethenoxymethyl)-4-methoxybenzene；1-(2,2-difluoroethenoxymethyl)-4-methoxybenzene
• CAS: 446867-21-6
• 化学式: C₁₀H₁₀F₂O₂
• 分子量: 200.185
• InChiKey: LHKXAQSLRNXENE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-methoxybenzyl 2,2-difluorovinyl ether 在 正丁基锂 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 123.0h， 生成 (1R,4S,6S)-5,5-Difluoro-4-hydroxy-6-(4-methoxy-benzyloxy)-cyclohex-2-ene-1,1-dicarboxylic acid allyl ester methyl ester
  参考文献：
  名称：

  2,2-Disubstituted analogues of the natural hormone 1α,25-dihydroxyvitamin D 3 : chemistry and biology

  摘要：

  Six new 2, 2-disubstituted analogues of the natural hormone calcitriol have been prepared. Chemical novelty includes (1) the first example of an inverse-electron-demand Diels-Alder cycloaddition using a pyrone diene and a difluorinated vinyl ether dienophile, leading to difluorinated analogues 7 and (2) a conceptually streamlined approach to dimethylated 19-nor analogues 8. Analogues 7a and 8a are similar to calcitriol in terms of in vitro antiproliferative activity, but they are different from calcitriol in terms of transcriptional activity: difluorinated analogue 7a is 2-3 times more active transcriptionally than calcitriol, whereas dimethylated analogue 8a is 7.5 times less active transcriptionally. Whereas the in vivo calcemic activity of difluorinated analogue 7a is similar to that of calcitriol, dimethylated analogue 8a is considerably less calcemic than calcitriol. Dimethylated analogue 8a strongly suppresses parathyroid hormone (PTH) secretion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00058-5
• 作为产物：
  描述：

  4-methoxybenzyl 2,2,2-trifluoroethyl ether 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 以32%的产率得到p-methoxybenzyl 2,2-difluorovinyl ether
  参考文献：
  名称：

  2,2-Disubstituted analogues of the natural hormone 1α,25-dihydroxyvitamin D 3 : chemistry and biology

  摘要：

  Six new 2, 2-disubstituted analogues of the natural hormone calcitriol have been prepared. Chemical novelty includes (1) the first example of an inverse-electron-demand Diels-Alder cycloaddition using a pyrone diene and a difluorinated vinyl ether dienophile, leading to difluorinated analogues 7 and (2) a conceptually streamlined approach to dimethylated 19-nor analogues 8. Analogues 7a and 8a are similar to calcitriol in terms of in vitro antiproliferative activity, but they are different from calcitriol in terms of transcriptional activity: difluorinated analogue 7a is 2-3 times more active transcriptionally than calcitriol, whereas dimethylated analogue 8a is 7.5 times less active transcriptionally. Whereas the in vivo calcemic activity of difluorinated analogue 7a is similar to that of calcitriol, dimethylated analogue 8a is considerably less calcemic than calcitriol. Dimethylated analogue 8a strongly suppresses parathyroid hormone (PTH) secretion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00058-5

文献信息

• 2,2-Disubstituted analogues of the natural hormone 1α,25-dihydroxyvitamin D 3 : chemistry and biology
  作者：Gary H. Posner、Benjamin T. Woodard、Kenneth R. Crawford、Sara Peleg、Alex J. Brown、Patrick Dolan、Thomas W. Kensler

  DOI：10.1016/s0968-0896(02)00058-5

  日期：2002.7

  Six new 2, 2-disubstituted analogues of the natural hormone calcitriol have been prepared. Chemical novelty includes (1) the first example of an inverse-electron-demand Diels-Alder cycloaddition using a pyrone diene and a difluorinated vinyl ether dienophile, leading to difluorinated analogues 7 and (2) a conceptually streamlined approach to dimethylated 19-nor analogues 8. Analogues 7a and 8a are similar to calcitriol in terms of in vitro antiproliferative activity, but they are different from calcitriol in terms of transcriptional activity: difluorinated analogue 7a is 2-3 times more active transcriptionally than calcitriol, whereas dimethylated analogue 8a is 7.5 times less active transcriptionally. Whereas the in vivo calcemic activity of difluorinated analogue 7a is similar to that of calcitriol, dimethylated analogue 8a is considerably less calcemic than calcitriol. Dimethylated analogue 8a strongly suppresses parathyroid hormone (PTH) secretion. (C) 2002 Elsevier Science Ltd. All rights reserved.