3-乙烯基-4-甲氧基环丁-3-烯-1,2-二酮 | 124022-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙烯基-4-甲氧基环丁-3-烯-1,2-二酮
• 英文名称: 3-ethenyl-4-methoxycyclobutene-1,2-dione
• 英文别名: 3-ethenyl-4-methoxy-3-cyclobutene-1,2-dione；2-ethenyl-3-methoxycyclobutendione；3-Cyclobutene-1,2-dione, 3-ethenyl-4-methoxy-；3-ethenyl-4-methoxycyclobut-3-ene-1,2-dione
• CAS: 124022-02-2
• 化学式: C₇H₆O₃
• 分子量: 138.123
• InChiKey: OCKUUOZMOQDCCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-乙烯基-4-甲氧基环丁-3-烯-1,2-二酮 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到3-(2-Bromoethyl)-4-methoxycyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  由3-乙烯基-4-甲氧基-环丁烯-1,2-二酮合成取代的环丁二烯

  摘要：

  描述了由二甲基二甲基酸酯合成3-乙烯基-4-甲氧基环丁烯-1，2-二酮。观察到该化合物容易地将碳和非碳亲核试剂两者都进行3-烯基的1，6-加成。因此，它用作合成多种取代的环丁二烯的通用起始原料，这些取代的环丁二酮是多种其他环系统的方便起始原料。

  DOI：

  10.1016/s0040-4039(00)92025-2
• 作为产物：
  描述：

  在 三氟乙酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以6.55 g的产率得到3-乙烯基-4-甲氧基环丁-3-烯-1,2-二酮
  参考文献：
  名称：

  DIMETHYL SQUARATE AND ITS CONVERSION TO 3-ETHENYL-4-METHOXYCYCLOBUTENE-1,2-DIONE AND 2-BUTYL-6-ETHENYL-5-METHOXY-1,4-BENZOQUINONE

  摘要：

  DOI：

  10.15227/orgsyn.076.0189

文献信息

• CYCLOBUTENEDIONE DERIVATIVE, NONAQUEOUS ELECTROLYTIC SOLUTION, AND LITHIUM ION SECONDARY BATTERY
  申请人：NEC Corporation

  公开号：US20170210764A1

  公开（公告）日：2017-07-27

  A nonaqueous electrolytic solution comprising a cyclobutenedione derivative represented by the following general formula (1): wherein R 1 represents an organic group having a carbon-carbon double bond or a carbon-carbon triple bond in its structure, and R 2 represents an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, a thioalkyl group having 1-6 carbon atoms, a substituted or unsubstituted thioaryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

  一种非水电解质溶液，包括以下通用式（1）所代表的环丁二酮衍生物：其中R1代表具有碳-碳双键或碳-碳三键结构的有机基团，R2代表具有1-6个碳原子的烷基基团，具有1-6个碳原子的烷氧基团，具有1-6个碳原子的硫代烷基基团，取代或未取代的硫代芳基团，取代或未取代的芳基团，或取代或未取代的杂芳基团。
• Cyclobutenedione derivative, nonaqueous electrolytic solution, and lithium ion secondary battery
  申请人：NEC Corporation

  公开号：US10374258B2

  公开（公告）日：2019-08-06

  A nonaqueous electrolytic solution comprising a cyclobutenedione derivative represented by the following general formula (1): wherein R1 represents an organic group having a carbon-carbon double bond or a carbon-carbon triple bond in its structure, and R2 represents an alkyl group having 1-6 carbon atoms, an alkoxy group having 1-6 carbon atoms, a thioalkyl group having 1-6 carbon atoms, a substituted or unsubstituted thioaryl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

  一种非水性电解溶液，包含由以下通式 (1) 代表的环丁二酮衍生物： 其中 R1 代表在其结构中具有碳碳双键或碳碳三键的有机基团，R2 代表具有 1-6 个碳原子的烷基、具有 1-6 个碳原子的烷氧基、具有 1-6 个碳原子的硫代烷基、取代或未取代的硫代芳基、取代或未取代的芳基或取代或未取代的杂芳基。
• Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Enantiomerically Pure Pyranoquinones from 4-(4-Oxo-1,6-enynyl)-4-hydroxycyclobutenones and 4-(4-Oxo-1,6-dialkynyl)-4-hydroxycyclobutenones
  作者：Yifeng Xiong、Haiji Xia、Harold W. Moore

  DOI：10.1021/jo00125a037

  日期：1995.10

  Thermolysis of 4-(4-oxo-1,6-enynyl)-4-hydroxycyclobutenones 23 in refluxing toluene provides an enantiospecific synthesis of pyranoquinones 27. The 4-methoxy analog 32 was shown to give a quinone methide 35 and ultimately the trimer 36.
• Synthesis of the bicyclo[3.2.0] ring systems from 4-allylcyclobutenones. Intramolecular ketene/alkene cycloadditions
  作者：Simon L. Xu、Haiji Xia、Harold W. Moore

  DOI：10.1021/jo00021a025

  日期：1991.10

  A general synthesis of bicyclo[3.2.0]heptenones from 4-allylcyclobutenones is described. The rearrangement is envisaged to involve an electrocyclic ring opening of the cyclobutenone and subsequent intramolecular 2 + 2 cycloaddition of the resulting vinylketene to the nonconjugated allylic alkene moiety. This method is particularly suitable for the synthesis of highly substituted derivatives since the regiochemistry of the substitution pattern is conveniently controlled. The scope of the rearrangement and the mechanism are discussed.
• Synthesis of p-chlorophenols (and -naphthols) from the thermal rearrangement of 4-chlorocyclobutenones
  作者：Simon L. Xu、Harold W. Moore

  DOI：10.1021/jo00027a057

  日期：1992.1

  A systematic study of the reaction of 4-hydroxycyclobutenones with thionyl chloride is reported. A useful model evolves from this study which allows the prediction of the site of chlorination for unsymmetrical examples. The chlorination is envisaged to involve the corresponding homoaromatic carbocation, and the site of chlorination takes place preferentially at the position substituted with the greater cation-stabilizing substituent. Specifically, this follows the general order of allyl > benzyl > alkyl > propargyl. The 4-chlorocyclobutenones prepared in this study were shown to be useful synthetic precursors to highly substituted chlorophenols and chloronaphthols.