1-溴丙烷-2-酮肟 | 62116-25-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-溴丙烷-2-酮肟
• 英文名称: α-bromoacetone oxime
• 英文别名: (Z,E)-bromo-acetone oxime；1-bromo-2-propanone oxime；bromoacetone oxime；1-bromo-propan-2-one oxime；bromo-acetone oxime；Brom-aceton-oxim；N-(1-bromopropan-2-ylidene)hydroxylamine
• CAS: 62116-25-0
• 化学式: C₃H₆BrNO
• 分子量: 151.991
• InChiKey: DSURKHJXZMTRML-UHFFFAOYSA-N

物化性质

• 熔点：
  36.5°C
• 密度：
  1.4233 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-溴丙烷-2-酮肟 、 piperidinium dithiobenzoate 生成 2-(hydroxyimino)propyl dithiobenzoate
  参考文献：
  名称：

  Ishida, Masaru; Nakanishi, Hirofumi; Kato, Shinzi, Heterocycles, 1985, vol. 23, # 1, p. 241

  摘要：

  DOI：
• 作为产物：
  描述：

  溴丙酮 在 盐酸羟胺 作用下， 生成 1-溴丙烷-2-酮肟
  参考文献：
  名称：

  Hetero-Diels–Alder reaction of [60]fullerene with nitrosoalkene

  摘要：

  A new type of stable C-60-fused dihydrooxazine derivatives was successfully prepared by the hetero-Diels-Alder reaction of C-60 With nitrosoalkene generated in situ by extrusion of HBr from the corresponding alpha-bromooxime. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.060

文献信息

• Synthesis of Pyrrole Derivatives from 5,6-Dihydro-4<i>H</i>-1,2-oxazines via Reductive Deoxygenation by Use of Fe₃(CO)₁₂
  作者：Saburo Nakanishi、Yoshio Otsuji、Keiji Itoh、Nobuaki Hayashi

  DOI：10.1246/bcsj.63.3595

  日期：1990.12

  derivatives are also obtained by the reaction of α-bromooximes with vinyl ethers and silyl enol ethers in the presence of Na2CO3. Dihydro-1,2-oxazines can be converted into pyrrole derivatives via reductive deoxygenation by treating with Fe3(CO)12 in moderate to excellent yields. Iron carbonyl complexes other than Fe3(CO)12 are also effective for the pyrrole-forming reaction. The efficiency of the complexes

  α-溴肟，如 α-溴苯乙酮肟和 3-溴-2-（羟基亚氨基）丙酸乙酯与烯胺反应，以良好的收率得到 5,6-二氢-4H-1,2-恶嗪。二氢-1,2-恶嗪衍生物也可通过α-溴肟与乙烯基醚和甲硅烷基烯醇醚在Na2CO3 存在下反应获得。二氢-1,2-恶嗪可以通过还原脱氧反应转化为吡咯衍生物，方法是用 Fe3(CO)12 处理，产率中等至极好。Fe3(CO)12 以外的羰基铁配合物对吡咯形成反应也有效。该反应中配合物的效率依次降低：Fe3(CO)12>>Et3NH[HFe3(CO)11]>Fe2(CO)9>>Fe(CO)5。二氢-1,2-恶嗪-和吡咯-形成反应都可以在一个烧瓶中进行，得到高产率的吡咯衍生物。
• Aza-Reformatsky-type reaction of α-iodomethyl ketone O-alkyl oximes promoted by titanium tetraiodide
  作者：Makoto Shimizu、Tadahiro Toyoda

  DOI：10.1039/b411127c

  日期：——

  Titanium tetraiodide promotes an aza-Reformatsky-type reaction of alpha-iodomethyl ketone O-alkyl oximes with carbonyl compounds to give beta-hydroxy ketone O-alkyl oximes in good to high yields.

  四碘化钛促进α-碘甲基酮O-烷基肟与羰基化合物的氮杂-Reformatsky型反应，从而以良好或高收率得到β-羟基酮O-烷基肟。
• Hippeli, Claudia; Reissig, Hans-Ulrich, Liebigs Annalen der Chemie, 1990, p. 217 - 226
  作者：Hippeli, Claudia、Reissig, Hans-Ulrich

  DOI：——

  日期：——
• Alkylation of alkali metal salts of aliphatic polynitro compounds ? A general method for preparing different types of polynitro derivatives
  作者：S. A. Shevelev、V. I. Erashko、A. A. Fainzil'berg

  DOI：10.1007/bf00920895

  日期：1976.12
• Stereochemical and electronic interaction studies of α-heterosubstituted acetone oximes
  作者：P.R Olivato、D.S Ribeiro、R Rittner、Y Hase、D del Pra、G Bombieri

  DOI：10.1016/0584-8539(95)01409-n

  日期：1995.8

  The free nu(C=N) bands in the IR spectra of some alpha-heterosubstituted acetone oximes show the existence of only a monomeric form in chloroform solutions at concentrations below 10(-2) M, while in carbon tetrachloride self-associated species are also present. The H-1 and C-13 NMR chemical shift data indicate the predominance of the E over the Z isomer. The Delta nu(C=N), frequency shifts and molecular mechanics calculations strongly suggest that the oximes are in the gauche conformation. X-ray diffraction data have shown that the single dimethylaminoacetone oxime isomer exists in the E configuration and gauche conformation. Non-additivity effects for the ir-methylene carbon chemical shifts seem to indicate the occurrence of a pi(C=N)/sigma(C-X)* interaction besides the pi(C=N)*/sigma(C-X) hyperconjugative interaction.