(2R,1S)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanol | 1403476-92-5

• 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: (2R,1S)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanol
• 英文别名: (1S)-1-[(2R)-2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl]-2,2-difluoroethanol
• CAS: 1403476-92-5
• 化学式: C₁₄H₁₈F₂O₃
• 分子量: 272.292
• InChiKey: ABEWFUHEBUWAKQ-IINYFYTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,1S)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanol 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 正己烷 、 异丙醇 为溶剂， 反应 0.5h， 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：

  (+/-)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanone 在 sodium tetrahydroborate 作用下， 以 乙醇 、 正己烷 、 异丙醇 为溶剂， 生成 (2R,1S)-1-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)-2,2-difluoroethanol
  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

文献信息

• Reduction of acetophenones with methyl fluorines and a bulky group on the aromatic ring using microorganisms and related enzymes
  作者：Chika Abe、Takahiro Sugawara、Takuya Machida、Toshinori Higashi、Kengo Hanaya、Mitsuru Shoji、Chen Cao、Takuro Yamamoto、Tomoko Matsuda、Takeshi Sugai

  DOI：10.1016/j.molcatb.2012.06.010

  日期：2012.10

  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.