7,7-difluorooctan-1-ol | 1311462-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,7-difluorooctan-1-ol
• 英文别名: 7,7-Difluoro-1-octanol
• CAS: 1311462-95-9
• 化学式: C₈H₁₆F₂O
• 分子量: 166.211
• InChiKey: ILPCVHCUYKVPQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,7-difluorooctan-1-ol 、 (R)-2-乙酰氧基-2-苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 7,7-difluorooctyl (R)-2-acetoxy-2-phenylacetate
  参考文献：
  名称：

  Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)

  摘要：

  gem-Difluoromethylene substituted molecules constitute a distinct class of fluorinated compounds. In this study, special chemistry has been developed for their preparation based on the highly selective terminal hydroxylation of these gem-difluorinated octanes by AlkB (alkane hydroxylase) from Pseudomonas putida Gpo1 to form gem-difluorinated octan-1-ols. The hydroxylation reaction is performed by whole-cell catalysis. Identification of the distal- and proximal-hydroxylation products was made by H-1, C-13, and F-19 NMR; GC and GC/MSD; and/or by comparison with authentic standards in GC. To the best of our knowledge, we have obtained the first synthesis of 2,2-, 3,3- and 4,4-difluorooctan-1-ols, from simple and inexpensive starting materials. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.101
• 作为产物：
  描述：

  2,2-Difluor-octan 在 E_. coli-alkane hydroxylase whole-cell system 作用下， 反应 3.0h， 以68%的产率得到7,7-difluorooctan-1-ol
  参考文献：
  名称：

  Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)

  摘要：

  gem-Difluoromethylene substituted molecules constitute a distinct class of fluorinated compounds. In this study, special chemistry has been developed for their preparation based on the highly selective terminal hydroxylation of these gem-difluorinated octanes by AlkB (alkane hydroxylase) from Pseudomonas putida Gpo1 to form gem-difluorinated octan-1-ols. The hydroxylation reaction is performed by whole-cell catalysis. Identification of the distal- and proximal-hydroxylation products was made by H-1, C-13, and F-19 NMR; GC and GC/MSD; and/or by comparison with authentic standards in GC. To the best of our knowledge, we have obtained the first synthesis of 2,2-, 3,3- and 4,4-difluorooctan-1-ols, from simple and inexpensive starting materials. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.101

文献信息

• Regio-selective hydroxylation of gem-difluorinated octanes by alkane hydroxylase (AlkB)
  作者：Ravirala Ramu、Chun-Wei Chang、Ho-Husan Chou、Li-Lan Wu、Chih-Hsiang Chiang、Steve S.-F. Yu

  DOI：10.1016/j.tetlet.2011.03.101

  日期：2011.6

  gem-Difluoromethylene substituted molecules constitute a distinct class of fluorinated compounds. In this study, special chemistry has been developed for their preparation based on the highly selective terminal hydroxylation of these gem-difluorinated octanes by AlkB (alkane hydroxylase) from Pseudomonas putida Gpo1 to form gem-difluorinated octan-1-ols. The hydroxylation reaction is performed by whole-cell catalysis. Identification of the distal- and proximal-hydroxylation products was made by H-1, C-13, and F-19 NMR; GC and GC/MSD; and/or by comparison with authentic standards in GC. To the best of our knowledge, we have obtained the first synthesis of 2,2-, 3,3- and 4,4-difluorooctan-1-ols, from simple and inexpensive starting materials. (C) 2011 Elsevier Ltd. All rights reserved.