3-hexynyl-4-methoxy-3-cyclobutene-1,2-dione | 124022-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hexynyl-4-methoxy-3-cyclobutene-1,2-dione
• 英文别名: 3-(1-hexynyl)-4-methoxy-3-cyclobutene-1,2-dione；3-Hex-1-ynyl-4-methoxycyclobut-3-ene-1,2-dione
• CAS: 124022-03-3
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: PSOQRQAWJJSPJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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-hexynyl-4-methoxy-3-cyclobutene-1,2-dione 在 吡啶 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 4-chloro-2-(1-hexynyl)-3-methoxy-4-phenyl-2-cyclobuten-1-one
  参考文献：
  名称：

  Synthesis of p-chlorophenols (and -naphthols) from the thermal rearrangement of 4-chlorocyclobutenones

  摘要：

  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.

  DOI：

  10.1021/jo00027a057

文献信息

• Synthesis of indolizine-5,8-diones and [3.2.2]cyclazines
  作者：Benjamin R. Yerxa、Harold W. Moore

  DOI：10.1016/s0040-4039(00)74750-2

  日期：1992.12

  subsequent oxidation to the rare indolizine-5,8-diones is described. When the rearrangement is carried out in the presence of DMAD the indolizines are trapped in an 8+2 cycloaddition to give [3.2.2]cyclazines.

  描述了热诱导的4-（1-吡咯基）-4-三甲基甲硅烷氧基环丁烯酮的环膨胀成5-羟基-8-三甲基甲硅烷氧基吲哚并随后氧化成稀有的吲哚嗪-5，8-二酮。当在DMAD存在下进行重排时，吲哚嗪被困在8 + 2环加成反应中，生成[3.2.2]环嗪。
• Stereocontrolled Synthesis of 3-Acyl-4-alkoxy-5-aryl-1,2,4(E)-pentatrienes and Their Subsequent Electrocyclization to Naphthalenes
  作者：Philip Turnbull、Harold W. Moore

  DOI：10.1021/jo00116a005

  日期：1995.6
• 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.
• Rearrangements of cyclobutenones. Conversion of selected 4-allylcyclobutenones to bicyclo[3.2.0]heptenones
  作者：Simon L. Xu、Harold W. Moore

  DOI：10.1021/jo00287a010

  日期：1989.12
• XU, SIMON L.;MOORE, HAROLD W., J. ORG. CHEM., 54,(1989) N6, C. 6018-6021
  作者：XU, SIMON L.、MOORE, HAROLD W.

  DOI：——

  日期：——