1-氯-2-丙酮肟 | 671-59-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 1-氯-2-丙酮肟
• 英文名称: chloroacetone oxime
• 英文别名: 1-Chloro-2-(hydroxyimino)propane；(Z,E)-chloro-acetone oxime；chloropropanone oxime；1-chloroacetoxime；1-chloro-propan-2-one oxime；2-Propanone, 1-chloro-, oxime；N-(1-chloropropan-2-ylidene)hydroxylamine
• CAS: 671-59-0
• 化学式: C₃H₆ClNO
• mdl: MFCD01696612
• 分子量: 107.54
• InChiKey: ADYDCWWHQBOFHC-UHFFFAOYSA-N

物化性质

• 沸点：
  54.5-55.0 °C(Press: 2 Torr)
• 密度：
  1.2093 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  1-氯-2-丙酮肟 在 氨 作用下， 生成 tris(2-hydroxyiminopropyl)amine
  参考文献：
  名称：

  Matthaiopoulos, Chemische Berichte, 1898, vol. 31, p. 2396

  摘要：

  DOI：
• 作为产物：
  描述：

  4-chloro-3-methyl-3-nitroso-butan-2-one N,N'-dimer 以 甲醇 为溶剂， 生成 1-氯-2-丙酮肟
  参考文献：
  名称：

  Ogloblin,K.A.; Potekhin,A.A., Doklady Chemistry, 1964, vol. 159, p. 1280 - 1283

  摘要：

  DOI：

文献信息

• Oxime compounds, their use, and intermediates for their production
  申请人：Sumitomo Chemical Company, Limited

  公开号：US20020019569A1

  公开（公告）日：2002-02-14

  Oxime compounds of formula (1) 1 wherein R 1 , R 2 , and R 3 are independently halogen, C 1 -C 3 alkyl, C 1 -C 3 halolalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, nitro, or cyano; R 4 is 3,3-dihalogeno-2-propenyl; a is an integer of 0 to 2; Y is oxygen, sulfur, or NH; Z is oxygen, sulfur, or NR 5 wherein R 5 is hydrogen, acetyl, or C 1 -C 3 alkyl; and X is of formula (2) 2 insecticidal/acaricidal agents containing them as active ingredients; and intermediates for their production.

  式（1）中的肟化合物，其中R1、R2和R3分别独立地是卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、硝基或氰基；R4是3,3-二卤代-2-丙烯基；a是0到2的整数；Y是氧、硫或NH；Z是氧、硫或NR5，其中R5是氢、乙酰基或C1-C3烷基；X是式（2）的化合物；含有它们作为活性成分的杀虫/杀螨剂；以及它们的生产中间体。
• Nitrosoalkenes: Synthesis and Reactivity
  作者：Eric Francotte、Robert Merényi、Brigitte Vandenbulcke-Coyette、Heinz-Günther Viehe

  DOI：10.1002/hlca.19810640425

  日期：1981.6.10

  2 can be substituted by alkoxy groups. Two kinds of cycloaddition reaction of 1 have been observed: (i) reaction of the NO group with dienes gives 3, 6-dihydrooxazine derivatives 6 which isomerise to epoxyepimines 7 in most cases of β-substituted nitrosoalkenes; (ii) if 4, 5-dihydrooxazines 22 are obtained, the cycloaddition of the nitrosoalkenes as 4π-component is presumed.

  已经合成并表征了一些α-和β-卤代亚硝基烯烃1。肟前体2的卤素原子可以被烷氧基取代。两种环加成反应的1已经观察到：（i）所述NO基团与二烯烃的反应得到3,6-二氢恶嗪衍生物6，其异构化成epoxyepimines 7在β取代nitrosoalkenes的大多数情况下; （ii）如果获得4，5-二氢恶嗪22，则推测亚硝基烯烃作为4π-组分的环加成。
• Synthesis and Cyclization Reaction of 2-(Hydroxyimino)alkyl<i>N,N</i>-Dialkylthiocarbamates,<i>S</i>-[2-(Hydroxyimino)alkyl]<i>O</i>-Methyl Dithiocarbonate, and Alkyl 2-(Hydroxyimino)alkyl Trithiocarbonates
  作者：Masaru Ishida、Kiyoshi Ichikawa、Masahiko Asano、Hirofumi Nakanishi、Shinzi Kato

  DOI：10.1055/s-1987-27940

  日期：——

  2-(Hydroxyimino)alkyl dialkyldithiocarbamates and alkyl 2-(hydroxyimino)alkyl trithiocarbonates react with tosyl isocyanate as dehydrating agent to give bis(4-isothiazolyl) disulfides in moderate yields. However, treatment of S-[2-(hydroxyimino)phenylethyl] O-methyl dithiocarbonate with tosyl isocyanate affords a novel heterocycle 3-phenyl-4H-1,5,2-oxathiazine-6-thione, in 49% yield.

  2-(羟基亚氨基)烷基二烷基二硫代氨基甲酸酯和 2-(羟基亚氨基)烷基三硫代碳酸酯与异氰酸甲苯酯作为脱水剂发生反应，生成二(4-异噻唑基)二硫化物，产率中等。然而，S-[2-（羟基亚氨基）苯基乙基] O-甲基二硫代碳酸酯与异氰酸对甲苯酯处理后，可得到一种新型杂环 3-苯基-4H-1,5,2-氧硫杂嗪-6-硫酮，产率为 49%。
• Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes
  作者：Yana A. Naumovich、Sema L. Ioffe、Alexey Yu. Sukhorukov

  DOI：10.1021/acs.joc.9b00924

  日期：2019.6.7

  oxides, phosphine–borane complexes, and phosphonium salts) was developed. The strategy exploits hitherto unknown Michael addition of PH-containing compounds (diphenylphosphine oxide, diisopropyl phosphite, phosphine–borane complexes, and triphenylphosphonium bromide) to unstable conjugated nitrosoalkenes, which are generated in situ from corresponding nitrosoacetals. The resulting α-phosphorus-substituted

  已开发出一种用于各种α-磷取代的肟（β-氧亚氨基烷基取代的膦酸酯，氧化膦，膦-硼烷配合物和phospho盐）的通用方法。该策略利用了迄今未知的迈克尔将含PH的化合物（二苯基氧化膦，亚磷酸二异丙酯，膦-硼烷络合物和溴化三苯基to）加成到不稳定的共轭亚硝基链中的方法，这些共轭亚硝基链是由相应的亚硝基缩醛原位生成的。所得的α-磷取代的肟可被认为是有用的P-，N-和O-配体，用于催化以及有价值的β-氨基膦酸酯的前体。
• Facile and Versatile Synthesis of Polydentate Metal Chelators with Both Amide and Oxime Donor Groups
  作者：Michael J. Goldcamp、Dell T. Rosa、Nicholas A. Landers、Sarah M. Mandel、Jeanette A. Krause Bauer、Michael J. Baldwin

  DOI：10.1055/s-2000-8724

  日期：——

  The first compounds with mixtures of deprotonateable amide and oxime donor groups that may act as tetradentate metal chelators were synthesized using the reagent N,N,N-triethyl-N-(propan-2-onyl oxime)ammonium chloride to add the oxime-containing arms to various amines with attached amides. This reagent avoids the complications due to competition between deprotonation of the oxime moiety and acid/base chemistry of the alkylation reaction. These compounds are based on either the simple "tripodal amine" framework, or on chiral, natural amino acid derivatives. The steric properties may be easily tuned by variation of the "R-groups" on the arms containing the functional groups.

  第一个可作为四齿金属螯合剂的化合物由可脱质子化的酰胺和肟供体基团的混合物组成，使用试剂N,N,N-三乙基-N-(丙-2-酮肟)氯化铵将含肟的臂添加到各种带有酰胺的胺上。该试剂避免了由于肟部分脱质子化和烷基化反应的酸碱化学之间的竞争而引起的复杂问题。这些化合物基于简单的“三足胺”框架或手性天然氨基酸衍生物。通过改变臂上含官能团的“R-基团”，可以很容易地调整空间性质。