1-(benzyloxy)octan-2-one | 1311463-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(benzyloxy)octan-2-one
• 英文别名: 1-phenylmethoxyoctan-2-one
• CAS: 1311463-06-5
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: LNZHLXLZVFHQBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(benzyloxy)octan-2-one 在 palladium 10% on activated carbon 、 氢气 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 24.25h， 生成 2,2-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
• 作为产物：
  描述：

  1,2-辛二醇 在 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 1-(benzyloxy)octan-2-one
  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

• Regioselective Wacker Oxidation of Internal Alkenes: Rapid Access to Functionalized Ketones Facilitated by Cross-Metathesis
  作者：Bill Morandi、Zachary K. Wickens、Robert H. Grubbs

  DOI：10.1002/anie.201303587

  日期：2013.9.9

  Wacka wacka: The title reaction makes use of a wide range of directing groups (DG) to enable the highly regioselective oxidation of alkenes, and occurs predictably at the distal position. Both E and Z alkenes afford valuable functionalized ketones and cross‐metathesis was shown to facilitate the preparation of the starting materials. BQ=benzoquinone.

  Wacka wacka：标题反应利用了广泛的导向基团（DG）来实现烯烃的高度区域选择性氧化，并且可预测地发生在末端位置。既Ë和Ž 烯烃得到有价值官能酮和交叉复分解显示出促进起始原料的制备。BQ ＝苯醌。