1,1-Dichlor-4-methoxy-3-penten-2-on | 83124-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-Dichlor-4-methoxy-3-penten-2-on
• 英文别名: 5,5-Dichloro-2-methoxy-2-penten-4-one；1,1-dichloro-4-methoxy-3-penten-2-one；1,1-Dichloro-4-methoxypent-3-en-2-one；1,1-dichloro-4-methoxypent-3-en-2-one
• CAS: 83124-78-1
• 化学式: C₆H₈Cl₂O₂
• 分子量: 183.034
• InChiKey: YTMBVDBQESBQLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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-Dichlor-4-methoxy-3-penten-2-on 在 盐酸肼 作用下， 以 乙醇 为溶剂， 以83%的产率得到5-dichloromethyl-3-methyl-1H-pyrazole
  参考文献：
  名称：

  无溶剂合成β-烯氨基二氯甲基酮的途径及其在合成新型5-dichloromethyl-1H-吡唑类化合物中的应用

  摘要：

  制备一系列五个4-氨基-1,1-二氯-3-戊烯-2-酮的有效方法[CHCl 2 C（O）CHC（Me）NR 1 R 2，其中R 1 / R 2 = H / PH，H / BN，H / CH 2 CH 2 OH，（CH 2）4 ，（CH 2）2 O（CH 2）2]来自1,1-二氯-4-甲氧基-3-戊烯-2-的无溶剂反应与伯胺和仲胺的反应。1,1-二氯-4-甲氧基-3-戊-2-酮与盐酸肼，苯肼盐酸盐和氨基脲盐酸盐反应制得5-二氯甲基-3-甲基吡唑。氨基胍盐酸盐和1,2-二甲基肼二盐酸盐也与1,1-二氯-4-甲氧基-3-戊二-2-酮反应，得到5-二氯甲基-3-甲基吡唑啉和5-二氯甲基1,2,3-分别为三甲基氯化吡唑鎓。所有环缩合反应均按照一锅法进行。J.杂环化​​学，（2009）。

  DOI：

  10.1002/jhet.227
• 作为产物：
  描述：

  二氯乙酰氯 、 2-甲氧基丙烯 在 吡啶 作用下， 反应 3.0h， 以79%的产率得到1,1-Dichlor-4-methoxy-3-penten-2-on
  参考文献：
  名称：

  Enol ethers and acetals: acylation with dichloroacetyl, acetyl and benzoyl chloride in ionic liquid medium

  摘要：

  Synthesis of 4-alkoxy-1,1-dichloro-3-alken-2-ones [CHCl2C(O)C(R-2=C(R-1)-OR, where R, R-1, R-2 = Et, H, H; Me, Me, H; Et, H, Me; Me, -(CH2)(2)-; Me, -(CH2)(3)-; Et, Et, H; Et, Bu, H; Et, i-Pr, H; Et, i-Bu, H; Me, Ph, H; Me, thien-2-yl, H] from acylation of enol ethers and acetals with dichloroacetyl chloride, in ionic liquid ([BMIM]BF4] or [BMIM][PF6]) is reported. The synthesis of alkenones [R-3-C(O)C(R-2=C(R1)-OR], where R/R-1/R-2/R-3 = Et/H/H/Ph, t-Bu/H/H/Ph, Me/-(CH2)(4)/Ph. Me/-(CH2)(4)/Me] from the reaction of enol ethers with benzoyl chloride or acetyl chloride, in ionic liquid [BMIM][BF4], is also reported. Last products are described for the first time. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.163

文献信息

• An ionic liquid as reaction medium for the synthesis of halo-containing β-enaminones at room temperature
  作者：Marcos A. P. Martins、Emerson A. Guarda、Clarissa P. Frizzo、Mara R. B. Marzari、Dayse N. Moreira、Nilo Zanatta、Helio G. Bonacorso

  DOI：10.1007/s00706-008-0923-3

  日期：2008.11

  , Et , Bu , allyl, tert -amyl, CH2CH2OH, Bn , Ph ] were synthesized using the ionic liquid [bmim]BF4 at room temperature. It is demonstrated that this ionic liquid is a reaction medium suitable for the amination of β-alkoxyvinyl halomethyl ketones. The advantages of this method are the absence of solvents, short reaction times, and good yields.

  一系列二十个卤代甲基化的β-烯酮[ R C（O）CH = C（ R 1）N R 3 R 4，其中 R = CF 3，CCl 3，CHCl 2； R 1＝ H， Me ， Ph ； R 3 = H， Me ， Bu ， Et ； R 4 = Me ， Et ， Bu ，烯丙基， 叔 戊基，CH 2在室温下使用离子液体[bmim] BF 4合成CH 2 OH， Bn 和 Ph ] 。已经证明该离子液体是适合于β-烷氧基乙烯基卤代甲基酮的胺化的反应介质。该方法的优点是无溶剂，反应时间短，产率高。
• An efficient synthesis of 1-cyanoacetyl-5-halomethyl-4,5-dihydro-1H-pyrazoles in ionic liquid
  作者：Dayse N. Moreira、Clarissa P. Frizzo、Kelvis Longhi、Nilo Zanatta、Helio G. Bonacorso、Marcos A. P. Martins

  DOI：10.1007/s00706-008-0874-8

  日期：2008.9

  The synthesis of eleven 1-cyanoacetyl-5-hydroxy-5-halomethyl-4,5-dihydro-1H-pyrazoles from the reaction of 4-alkoxy-3-alken-2-ones f((RC)-C-3(O)C(R-2) = C(R-1)OR, where R-3 = CF3, CCl3, CHCl2, CO2 Et; R-2/R-1 = H/H, H/Me, H/Et, -(CH2)(4)-, Me/H, H/Pr, and R = Me, Et) with cyanoacetohydrazide is reported. The reaction was carried out in the ionic liquid ([bmim][BF4]) and molecular solvents. The results showed that when the ionic liquid was used as reaction medium, the reaction time was drastically decreased and the yield was improved.
• Effenberger, Franz; Maier, Roland; Schoenwaelder, Karl-Heinz, Chemische Berichte, 1982, vol. 115, p. 2766 - 2782
  作者：Effenberger, Franz、Maier, Roland、Schoenwaelder, Karl-Heinz、Ziegler, Thomas

  DOI：——

  日期：——
• Synthesis of novel quinolines using TsOH/ionic liquid under microwave
  作者：Liziê D. T. Prola、Lilian Buriol、Clarissa P. Frizzo、Guilherme S. Caleffi、Mara R. B. Marzari、Dayse N. Moreira、Helio G. Bonacorso、Nilo Zanatta、Marcos A. P. Martins

  DOI：10.1590/s0103-50532012005000030

  日期：——

  In this work, 3-haloacetyl-4-methylquinolines were synthesized from the reaction of 4-alkoxy-3-alken-2-ones [(RC)-C-1(O)CH=C(R-2)OCH3, where R-1 = CF3, CCl3, CHCl2, CF2Cl, CF2CF3 and R-2 = Me, Et, Pr, Bu, i-Bu and i-Pe] and 2-aminoacetophenone. The reaction was performed in ionic liquid and 4-toluene sulfonic acid under microwave irradiation. Results showed that the catalytic method was effective. Products were formed in a short time (10-20 min) and presented good yields (70-91%).
• A Useful One-Step Synthesis of β-Trihaloacetylvinyl Ethers and Trihaloacetylketene Acetals
  作者：Masaru Hojo、Ryōichi Masuda、Etsuji Okada

  DOI：10.1055/s-1986-31852

  日期：——