(+/-)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanone | 1403476-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (+/-)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanone
• CAS: 1403476-87-8
• 化学式: C₁₄H₁₆F₂O₃
• 分子量: 270.276
• InChiKey: DTLMYCPHQRQXHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanone 在 吡啶 、 4-二甲氨基吡啶 、 葡萄糖 作用下， 反应 48.5h， 生成
  参考文献：
  名称：

  Reduction of acetophenones with methyl fluorines and a bulky group on the aromatic ring using microorganisms and related enzymes

  摘要：

  Whole-cell yeasts and mold-catalyzed reduction of two fluorinated acetophenone derivatives with very bulky substituents on ortho position of aromatic ring, (+/-)-1'-(2-tert-buty1-2-methyl-1,3-benzodioxo1-4-yl)-2',2'-difluoroethanone and (+/-)-1'-(2-tert-buty1-2-methyl-1,3-benzodioxol-4-yl)2',2',2'-trifluoroethanone were examined. On the former substrate, Geotrichum candidum NBRC 5767 showed high re-facially selective attack of hydride, while with Pichia angusta JCM 3620, complementary si-facially selective attack proceeded. G. candidum NBRC 5767 was revealed to be potent biocatalyst which provides (1'S)-alcohols from both substrates in a highly facially selective manner. Some unknown reductases were suggested responsible for those reductions, other than so far having been reported acetophenone reductase and trifluoromethyl ketone reductase from G. candidum, comparing the results obtained by applying those enzymes. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.06.010
• 作为产物：
  描述：

  二氟乙酸乙酯 、 2-tert-butyl-2-methyl-1,3-benzodioxole 在 正丁基锂 、 四甲基乙二胺 作用下， 以 正己烷 为溶剂， 以83%的产率得到(+/-)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanone
  参考文献：
  名称：

  Reduction of acetophenones with methyl fluorines and a bulky group on the aromatic ring using microorganisms and related enzymes

  摘要：

  Whole-cell yeasts and mold-catalyzed reduction of two fluorinated acetophenone derivatives with very bulky substituents on ortho position of aromatic ring, (+/-)-1'-(2-tert-buty1-2-methyl-1,3-benzodioxo1-4-yl)-2',2'-difluoroethanone and (+/-)-1'-(2-tert-buty1-2-methyl-1,3-benzodioxol-4-yl)2',2',2'-trifluoroethanone were examined. On the former substrate, Geotrichum candidum NBRC 5767 showed high re-facially selective attack of hydride, while with Pichia angusta JCM 3620, complementary si-facially selective attack proceeded. G. candidum NBRC 5767 was revealed to be potent biocatalyst which provides (1'S)-alcohols from both substrates in a highly facially selective manner. Some unknown reductases were suggested responsible for those reductions, other than so far having been reported acetophenone reductase and trifluoromethyl ketone reductase from G. candidum, comparing the results obtained by applying those enzymes. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2012.06.010