cyclopentanone O-((perfluorophenyl)methyl)oxime

• 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: cyclopentanone O-((perfluorophenyl)methyl)oxime
• 英文别名: Cyclopentanone oxime, o-[(pentafluorophenyl)methyl]-；N-[(2,3,4,5,6-pentafluorophenyl)methoxy]cyclopentanimine
• 化学式: C₁₂H₁₀F₅NO
• 分子量: 279.21
• InChiKey: DROCHUGRBXAIGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	O-(2,3,4,5,6-pentafluorobenzyl)hydroxylamine	72915-12-9	C7H4F5NO	213.107

反应信息

• 作为反应物：
  描述：

  cyclopentanone O-((perfluorophenyl)methyl)oxime 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 以81%的产率得到N-cyclopentyl-O-((perfluorophenyl)methyl)hydroxylamine
  参考文献：
  名称：

  铑催化重氮酰胺环化合成N-(2,3,4,5,6-五氟苄氧基)-γ-内酰胺

  摘要：

  描述了 N-(2,3,4,5,6-五氟-苄氧基) 重氮酰胺的铑催化环化，产生相应的 γ-内酰胺。环化基于分子内催化插入 C-H 键。获得了 14 种内酰胺，产率高达 91%，ee 高达 88%。加巴喷丁盐酸盐，一种 GABA 类似物，也通过这种方法合成，这表明 2,3,4,5,6-五氟苄氧基的脱保护是可能的。

  DOI：

  10.1002/ejoc.201402571
• 作为产物：
  描述：

  α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 一水合肼 、 sodium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 4.0h， 生成 cyclopentanone O-((perfluorophenyl)methyl)oxime
  参考文献：
  名称：

  铑催化重氮酰胺环化合成N-(2,3,4,5,6-五氟苄氧基)-γ-内酰胺

  摘要：

  描述了 N-(2,3,4,5,6-五氟-苄氧基) 重氮酰胺的铑催化环化，产生相应的 γ-内酰胺。环化基于分子内催化插入 C-H 键。获得了 14 种内酰胺，产率高达 91%，ee 高达 88%。加巴喷丁盐酸盐，一种 GABA 类似物，也通过这种方法合成，这表明 2,3,4,5,6-五氟苄氧基的脱保护是可能的。

  DOI：

  10.1002/ejoc.201402571

文献信息

• Identification of New Ozone Disinfection Byproducts in Drinking Water
  作者：Susan D. Richardson、Alfred D. Thruston、Tashia V. Caughran、Paul H. Chen、Timothy W. Collette、Terrance L. Floyd、Kathleen M. Schenck、Benjamin W. Lykins、Guang-ri Sun、George Majetich

  DOI：10.1021/es981218c

  日期：1999.10.1

  Using a combination of spectral identification techniques-gas chromatography coupled with low- and high-resolution electron-impact mass spectrometry (GC/EI-MS), low- and high-resolution chemical ionization mass spectrometry (GC/CI-MS), and infrared spectroscopy (GC/ IR)-we identified many drinking water disinfection byproducts (DBPs) formed by ozone and combinations of ozone with chlorine and chloramine. Many of these DBPs have not been previously reported. In addition to conventional XAD resin extraction, both pentafluorobenzyl-hydroxylamine (PFBHA) and methylation derivatizations were used to aid in identifying some of the more polar DBPs. Many of the byproducts identified were not present in spectral library databases. The vast majority of the ozone DBPs identified contained oxygen in their structures, with no halogenated DBPs observed except when chlorine or chloramine was applied as a secondary disinfectant. In comparing byproducts formed by secondary treatment of chlorine or chloramine, chloramine appeared to form the same types of halogenated DBPs as chlorine, but they were generally fewer in number and lower in concentration. Most of the halogenated DB Ps that were formed by ozone-chlorine and ozone-chloramine treatments were also observed in samples treated with chlorine or chloramine only. A few DBPs, however, were formed at higher levels in the ozone-chlorine and ozone-chloramine samples, indicating that the combination of ozone and chlorine or chloramine is important in their formation. These DBPs included dichloroacetaldehyde and 1,1-dichloropropanone.
• Synthesis of<i>N</i>-(2,3,4,5,6-Pentafluorobenzyloxy)-γ-lactams by Rhodium-Catalyzed Cyclization of Diazo Amides
  作者：Marcin Budny、Magdalena Nowak、Andrzej Wojtczak、Andrzej Wolan

  DOI：10.1002/ejoc.201402571

  日期：2014.10

  Rhodium-catalyzed cyclization of N-(2,3,4,5,6-pentafluoro-benzyloxy) diazo amides leading to the corresponding γ-lactams is described. The cyclization is based on the intramolecular catalytic insertion into the C–H bond. Fourteen lactams were obtained with up to 91 % yield and 88 % ee. Gabapentin hydrochloride, a GABA analog, was also synthesized by this method, which shows that deprotection of the

  描述了 N-(2,3,4,5,6-五氟-苄氧基) 重氮酰胺的铑催化环化，产生相应的 γ-内酰胺。环化基于分子内催化插入 C-H 键。获得了 14 种内酰胺，产率高达 91%，ee 高达 88%。加巴喷丁盐酸盐，一种 GABA 类似物，也通过这种方法合成，这表明 2,3,4,5,6-五氟苄氧基的脱保护是可能的。