(E)-1,1,1-trichloro-4-methoxy-5-methylhex-3-en-2-one | 233272-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,1,1-trichloro-4-methoxy-5-methylhex-3-en-2-one
• CAS: 233272-58-7
• 化学式: C₈H₁₁Cl₃O₂
• 分子量: 245.533
• InChiKey: CURHRUPLVLVUBK-GQCTYLIASA-N

物化性质

• 沸点：
  233.578±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.278±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1,1,1-trichloro-4-methoxy-5-methylhex-3-en-2-one 在 吡啶 、 盐酸羟胺 作用下， 以 甲苯 为溶剂， 反应 0.1h， 以95%的产率得到3-Isopropyl-5-trichloromethyl-4,5-dihydro-isoxazol-5-ol
  参考文献：
  名称：

  Microwave assisted synthesis of 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazoles

  摘要：

  A series of 13 5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazoles have been synthesized in 78-96% yield by environmentally benign microwave induced techniques involving the cyclocondensation of 4-alkoxy-1,1,1-trichloro-3-alken-2-ones [CCl3C(O)C(R-2)=C(R-1)OR, where R-2=H, alkyl; R-1=H, alkyl, aryl and R=H, alkyl] with hydroxylamine using toluene as solvent. The advantages obtained by the use of microwave irradiation in relation to a classical method were demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01555-1
• 作为产物：
  描述：

  2,2-二甲氧基-3-甲基丁烷 、 三氯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到(E)-1,1,1-trichloro-4-methoxy-5-methylhex-3-en-2-one
  参考文献：
  名称：

  Regiospecific acylation of acetals. A convenient method to obtain β-methoxyvinyl trichloromethyl ketones

  摘要：

  The regiochemistry of the acylation of enol ethers, generated in situ, from acetals of unsymmetrical ketones is reported. These results demonstrate a convenient one-pot method to obtain a series of beta-methoxyvinyl trichloromethyl ketones [CCl3COCH=C(OMe)R, where R=Et, n-Bu, i-Pr, (CH2)(2)C(OMe)=CHC(O)CCl3 and (CH2)(5)CO2CH3)] in high yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00672-3

文献信息

• A Convenient Preparation of 4-Methyl- and 4-Phenylseleno-1,1,1-trihalo-3-alken-2-ones and their Usefulness in the Synthesis of 3-Trihalomethyl­isoselenazoles
  作者：Marcos A. Martins、Giovani P. Bastos、Adilson P. Sinhorin、Nilo E. Zimmermann、Helio G. Bonacorso、Nilo Zanatta

  DOI：10.1055/s-2002-34854

  日期：——

  reaction of 4-methylseleno- 1,1,1-trihalo-3-alken-2-ones with bromine and ammonia lead to 3-trihalomethylisoselenazoles in good yields. The usefulness of the trichloromethyl group as a carboxyl group precursor was demonstrated by the conversion of 5-ethyl-3-trichloromethylisoselenazole to 5-ethyl-3-carboxyisoselenazole acid.

  14 种 4-甲基-和 4-苯基硒-1,1,1-三卤代-3-烯烃-2-酮的便捷合成 [CX 3 C(O)CH=CR 1 SeR。其中 X = F, Cl; R = 我，博士；和R 1 = H，烷基，芳基来自相应的4-甲氧基-1,1,1-三卤代-3-烯烃-2-酮与甲基-或苯基硒醇在醚合三氟化硼存在下的反应。4-甲基硒代-1,1,1-三卤代-3-烯烃-2-酮与溴和氨的反应以良好的收率产生3-三卤代甲基异硒唑。通过将 5-乙基-3-三氯甲基异硒唑转化为 5-乙基-3-羧基异硒唑酸证明了三氯甲基作为羧基前体的有用性。
• β-Alkoxyvinyl trichloromethyl ketones as N-heterocyclic acylating agent. A new access to 5H-thiazolo[3,2-a]pyrimidin-5-ones
  作者：Helio G Bonacorso、Rogério V Lourega、Arci D Wastowski、Alex F.C Flores、Nilo Zanatta、Marcos A.P Martins

  DOI：10.1016/s0040-4039(02)02337-7

  日期：2002.12

  Using trichloromethyl substituent as convenient leaving group for the synthesis of interesting bi-heterocyclic compounds, a series of 6-methyl- and 7-alkyl(aryl)-5H-thiazolo[3,2-a]pyrimidin-5-ones, where alkyl=methyl, n-propyl, isopropyl, isobutyl, n-hexyl, isopentyl and aryl=phenyl, 4-toluyl, 4-chlorophenyl, 4-bromophenyl, 4-methoxyphenyl was obtained from a simple and regiospecific reaction of 4-alkoxy-1

  使用三氯甲基取代基作为方便的离去基团，用于合成有趣的双杂环化合物，一系列6-甲基和7-烷基（芳基）-5 H-噻唑并[3,2- a ]嘧啶-5-酮，其中烷基＝甲基，正丙基，异丙基，异丁基，正己基，异戊基和芳基＝苯基，通过4-烷氧基-的简单和区域特异性反应获得4-甲苯基，4-氯苯基，4-溴苯基，4-甲氧基苯基。 1,1,1-三氯-3-烯丙基-2-酮与2-氨基噻唑的收率良好（45–89％）。
• HALOACETYLATED ENOL ETHERS: 16[5] REGIOSPECIFIC SYNTHESIS OF 5-TRICHLOROMETHYL-PYRAZOLES
  作者：Alex F. C. Flores、Marcos A. P. Martins、Adriano Rosa、Darlene Correia Flores、Nilo Zanatta、Helio G. Bonacorsso

  DOI：10.1081/scc-120004150

  日期：2002.1

  ABSTRACT The regiospecific synthesis and isolation of three series of 5-trichloromethyl-pyrazoles 2f–j, 3a–j and 4a–j from the cyclocondensation of 1,1,1-trichloro-4-alkoxy-3-alken-2-ones (1a–f) or trichloroacetyl containing β-diketones (1g–j) with dry hydrazine and phenyl-hydrazine is reported. It was established by 1H- and 13C-NMR spectroscopy that the 5-hydroxy-5-trichloromethyl-4,5-dihydro-1H-pyrazole

  摘要 从 1,1,1-trichloro-4-alkoxy-3-alken-2-ones 的环缩合反应中区域特异性合成和分离了三个系列的 5-三氯甲基-吡唑 2f-j、3a-j 和 4a-j（ 1a-f) 或含三氯乙酰的 β-二酮 (1g-j) 与干燥的肼和苯肼被报道。通过 1H- 和 13C-NMR 光谱确定 5-羟基-5-三氯甲基-4,5-二氢-1H-吡唑中间体 2a-j 是定量形成的。
• Microwave-assisted synthesis of 5-trichloromethyl substituted 1-phenyl-1H-pyrazoles and 1,2-dimethylpyrazolium chlorides
  作者：Marcos A.P Martins、Claudio M.P Pereira、Paulo Beck、Pablo Machado、Sidnei Moura、Marcos V.M Teixeira、Helio G Bonacorso、Nilo Zanatta

  DOI：10.1016/s0040-4039(03)01633-2

  日期：2003.8

  A series of five 5-trichloromethyl-1-phenyl-1H-pyrazoles and six 5-trichloromethyl-1,2-dimethylpyrazolium chlorides have been synthesized in 80-98% yield by environmentally benign microwave induced techniques involving the cyclocondensation of 4-alkoxy-1,1,1-trichloro-3-alken-2-oneS [Cl3C(O)C(R-1)=C(R-1)OR, where R-2=H, Me; R-1=H, alkyl, phenyl and R=Me, Et] with phenyl hydrazine and 1,2-dimethylhydrazine dihydrochloride, respectively, using toluene as solvent. The use of microwave and classical methods are comparable for making pyrazoles, but the formation of pyrazolium chlorides can be achieved in a significant shorter time, and in some cases better yield. (C) 2003 Elsevier Ltd. All rights reserved.