1,1,1-trichloro-4-methoxy-4-phenyl-3-buten-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,1,1-trichloro-4-methoxy-4-phenyl-3-buten-2-one
• 英文别名: (E)-1,1,1-trichloro-4-methoxy-4-phenylbut-3-en-2-one
• 化学式: C₁₁H₉Cl₃O₂
• 分子量: 279.55
• InChiKey: SDZUUSJFEZWWPU-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1,1,1-trichloro-4-methoxy-4-phenyl-3-buten-2-one 在 吡啶 、 盐酸羟胺 作用下， 以 甲苯 为溶剂， 反应 0.1h， 以90%的产率得到3-phenyl-5-hydroxy-5-trichloromethyl-4,5-dihydroisoxazole
  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

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％）。
• A Convenient Synthesis of 5- and 6-Substituted 2-Phenyl-3<i>H</i>-pyrimidin-4-ones
  作者：Nilo Zanatta、Leonardo Fantinel、Rogério Lourega、Helio Bonacorso、Marcos Martins

  DOI：10.1055/s-2008-1032032

  日期：2008.2

  A simple and convenient one-pot procedure for the synthesis of 5- and 6-substituted 2-phenyl-3 H-pyrimidin-4-ones by the condensation of 4-alkoxy-1,1,1-trichloroalk-3-en-2-ones with benz-amidine hydrochloride is described.

  通过 4-alkoxy-1,1,1-trichloroalk-3-en- 缩合合成 5-和 6-取代的 2-苯基-3 H-嘧啶-4-酮的简单方便的一锅法描述了与苯甲脒盐酸盐的 2-ones。
• HALOACETYLATED ENOL ETHERS. XVII.1* A CONVENIENT SYNTHESIS OF 5-TRICHLOROMETHYL-1,2-DIMETHYL- 1H-PYRAZOLIUM CHLORIDES
  作者：Marcos Martins、Claudio Pereira、Adilson Sinhorin、Giovani Bastos、Nilo Zimmermann、Adriano Rosa、Helio Bonacorso、Nilo Zanatta

  DOI：10.1081/scc-120002126

  日期：——

  ABSTRACT The one-pot synthesis of nine 5-trichloromethyl-1,2-dimethyl-1H-pyrazolium chlorides 2 from the cyclocondensation of 4-alkoxy-1,1,1-trichloro-3-alken-2-ones [CCl3C(O)C(R2)= C(R1)OR, where R1 = H, Me, Et, n-Pr, (CH2)5CO2Et, CH2Br, Ph, 4-Br-C6H4; R2 = H, Me; and R = Me, Et] with 1,2-dimethylhydrazine is reported. For Part 16, see Ref. [12].

  摘要 通过 4-烷氧基-1,1,1-三氯-3-烯烃-2-酮 [CCl3C(O )C(R2)= C(R1)OR，其中 R1 = H、Me、Et、n-Pr、(CH2)5CO2Et、 Br、Ph、4-Br-C6H4；R2 = H，我；和 R = Me, Et] 与 1,2-二甲基肼报道。对于第 16 部分，请参阅参考资料。[12]。
• One-Pot Synthesis of 3(5)-Ethoxycarbonylpyrazoles
  作者：Marcos A.P. Martins、Rogério Freitag、Alex F.C. Flores、Nilo Zanatta

  DOI：10.1055/s-1995-4147

  日期：1995.12

  A one-pot synthesis of ethoxycarbonylpyrazoles 2a-e, by the cyclocondensation of β-alkoxyvinyl trichloromethyl ketones 1a-e with hydrazine hydrochloride under mild conditions, is reported. A study using compounds 1a-e with different substituents proved that these are versatile building blocks for the synthesis of pyrazole derivatives, having a 3(5)-ethoxycarbonyl substituent, in good yields (70-91%).

  报告了在温和条件下，通过 δ- 烷氧基乙烯基三氯甲基酮 1a-e 与盐酸肼的环缩合，一步合成乙氧羰基吡唑 2a-e。使用具有不同取代基的化合物 1a-e 进行的研究证明，这些化合物是合成具有 3(5)- 乙氧基羰基取代基的吡唑衍生物的通用构筑基块，而且产率良好（70-91%）。