4,4-二氟-5-(2'-甲氧基-乙氧基甲氧基)-癸-1,5,9-三烯-3-醇 | 1008799-37-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 中文名称: 4,4-二氟-5-(2'-甲氧基-乙氧基甲氧基)-癸-1,5,9-三烯-3-醇
• 英文名称: 4,4-difluoro-5-(2'-methoxy-ethoxymethoxy)-deca-1,5,9-trien-3-ol
• 英文别名: (5Z)-4,4-difluoro-5-(2-methoxyethoxymethoxy)deca-1,5,9-trien-3-ol
• CAS: 1008799-37-8
• 化学式: C₁₄H₂₂F₂O₄
• 分子量: 292.323
• InChiKey: AMRGFRMAWXCOHI-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4-二氟-5-(2'-甲氧基-乙氧基甲氧基)-癸-1,5,9-三烯-3-醇 在 Grubbs catalyst first generation 、 disodium ethylenediaminetetraacetic acid titanium(IV) isopropylate 、 甲醇 、 4-二甲氨基吡啶 、 Oxone 、 氯化亚砜 、 1,1,1-三氟丙酮 、 poly(vinylpyridine) 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 36.0h， 生成 2RS-benzoyloxy-3,3-difluoro-9-oxa-(1SR,8SR)-bicyclo[6.1.0]nonan-4-one
  参考文献：
  名称：

  Total Syntheses of Conformationally Locked Difluorinated Pentopyranose Analogues and a Pentopyranosyl Phosphate Mimetic

  摘要：

  Trifluoroethanol has been elaborated, via a telescoped sequence involving a metalated difluoroenol, a difluoroallylic alcohol, [2,3]-Wittig rearrangement, and ultimately an RCM reaction and requiring minimal intermediate purification, to a number of cyclooctenone intermediates. Epoxidation of these intermediates followed by transannular ring opening or dihydroxylation, then transannular hemiacetalization delivers novel bicyclic analogues of pentopyranoses, which were elaborated (in one case) to an analogue of a glycosyl phosphate.

  DOI：

  10.1021/jo0620258
• 作为产物：
  描述：

  4-戊烯醛 在 sodium hydroxide 、 四丁基硫酸氢铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 23.5h， 生成 4,4-二氟-5-(2'-甲氧基-乙氧基甲氧基)-癸-1,5,9-三烯-3-醇
  参考文献：
  名称：

  Total Syntheses of Conformationally Locked Difluorinated Pentopyranose Analogues and a Pentopyranosyl Phosphate Mimetic

  摘要：

  Trifluoroethanol has been elaborated, via a telescoped sequence involving a metalated difluoroenol, a difluoroallylic alcohol, [2,3]-Wittig rearrangement, and ultimately an RCM reaction and requiring minimal intermediate purification, to a number of cyclooctenone intermediates. Epoxidation of these intermediates followed by transannular ring opening or dihydroxylation, then transannular hemiacetalization delivers novel bicyclic analogues of pentopyranoses, which were elaborated (in one case) to an analogue of a glycosyl phosphate.

  DOI：

  10.1021/jo0620258

文献信息

• Total Syntheses of Conformationally Locked Difluorinated Pentopyranose Analogues and a Pentopyranosyl Phosphate Mimetic
  作者：Jonathan A. L. Miles、Lisa Mitchell、Jonathan M. Percy、Kuldip Singh、E. Uneyama

  DOI：10.1021/jo0620258

  日期：2007.3.1

  Trifluoroethanol has been elaborated, via a telescoped sequence involving a metalated difluoroenol, a difluoroallylic alcohol, [2,3]-Wittig rearrangement, and ultimately an RCM reaction and requiring minimal intermediate purification, to a number of cyclooctenone intermediates. Epoxidation of these intermediates followed by transannular ring opening or dihydroxylation, then transannular hemiacetalization delivers novel bicyclic analogues of pentopyranoses, which were elaborated (in one case) to an analogue of a glycosyl phosphate.