dimethyl 3-vinylcyclobutene-1,2-dicarboxylate | 101774-07-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 3-vinylcyclobutene-1,2-dicarboxylate
• 英文别名: 1-Cyclobutene-1,2-dicarboxylic acid, 3-ethenyl-, dimethyl ester；dimethyl 3-ethenylcyclobutene-1,2-dicarboxylate
• CAS: 101774-07-6
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: MFFIPVCGDAAMPW-UHFFFAOYSA-N

物化性质

• 沸点：
  250.6±40.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 3-vinylcyclobutene-1,2-dicarboxylate 在 tetracarbonyl nickel 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 0.43h， 以36%的产率得到1,4-环己二烯-1,2-二羧酸二甲酯
  参考文献：
  名称：

  The nickel-promoted 1,3-migration of an sp2 center; ring expansion of a vinylcyclobutene

  摘要：

  DOI：

  10.1021/jo00361a031
• 作为产物：
  描述：

  (1S,2R)-1,2-dichloro-3-ethenylcyclobutane-1,2-dicarboxylic acid 在 tetracarbonyl nickel 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 dimethyl 3-vinylcyclobutene-1,2-dicarboxylate
  参考文献：
  名称：

  The nickel-promoted 1,3-migration of an sp2 center; ring expansion of a vinylcyclobutene

  摘要：

  DOI：

  10.1021/jo00361a031

文献信息

• A facile route to 3,7-cis-disubstituted cycloocta-1,5-diene-1,2,5,6- tetracarboxylates through photochemical [2 + 2]cycloaddition of 3-substituted cyclobutene-1,2-dicarboxylates and thermal isomerization†
  作者：Hisayuki Watanabe、Yasuyuki Nakajima、Michiaki Adachi、Hiroyasu Hotta、Kazutaka Arai、Yoshiyasu Baba、Carole Noutary、Satsuki Ichikawa、Tetsuo Kusumoto

  DOI：10.1039/a903942b

  日期：——

  Photochemical dimerization of 3-substituted cyclobutene-1,2-dicarboxylates followed by thermal isomerization gives regio- and stereo-selectively 3,7-cis-disubstituted cycloocta-1,5-diene-1,2,5,6-tetracarboxylates.

  3-取代环丁烯-1,2-二羧酸酯的光化学二聚反应随后经过热异构化，可以选择性地生成区域和立体选择性的 3,7-顺式二取代环辛烯-1,5-二烯-1,2,5,6-四羧酸酯。
• Isomerization of a vinylcyclobutene to a cyclohexadiene: a nickel(I) promoted rearrangement
  作者：Heajin Choi、James W. Hershberger、Allan R. Pinhas、Douglas M. Ho

  DOI：10.1021/om00054a072

  日期：1991.8

  The nickel-promoted isomerization of a 3-vinylcyclobutene to the corresponding 1,4-cyclohexadiene was studied by using (PPh3)2Ni(C2H4) as the nickel source. Through the use of chemical and electrochemical experiments, it was determined that nickel(I) and not nickel(0) promotes this isomerization reaction at room temperature. The corresponding platinum-vinylcyclobutene complex 4 has been characterized by a single-crystal X-ray diffraction study: C46H42O4P2Pt, monoclinic, P2(1)/n, with a = 10.774 (1) angstrom, b = 20.281 (4) angstrom, c = 18.297 (2) angstrom, beta = 97.37 (1)-degrees, Z = 4, R(F) = 0.0378, and R(w)(F) = 0.0371.
• Transition-metal-promoted conversion of dichlorovinylcyclobutanes to cyclohexadienes
  作者：Heajin Choi、Allan R. Pinhas

  DOI：10.1021/om00037a071

  日期：1992.1

  The nickel(0)- and iron(0)-promoted dechlorination of dimethyl 1,2-dichloro-3-vinylcyclobutane-1,2-dicarboxylate (1) to dimethyl 3-vinylcyclobutene-1,2-dicarboxylate (2) occurs faster in the trans isomer. Nickel(0) and nickel(I), but not iron(0), with promote the rearrangement of this vinylcyclobutene to dimethyl 1,4-cyclohexadiene-1,2-dicarboxylate (3). The effect of methyl substituents on these reactions indicate that the nickel must transfer to the vinyl group before the rearrangement can occur. It also was found that nickel will cleave exclusively the bond between an sp2- and an sp3-hybridized carbon.
• The rearrangement of 3-vinylcyclobutene derivatives promoted by metallic Lewis acids
  作者：Martin A Lovchik、Allan R Pinhas

  DOI：10.1016/s0022-328x(02)01585-1

  日期：2002.8

  The rearrangement of 3-vinylcyclobutene derivatives in the presence of metallic Lewis acids is discussed. Although most of the Lewis acids tried were too weak to cause any chemistry to occur, WCl6 and AlCl3 promote an interesting isomerization reaction. Especially significant is, for the first time, starting with a vinylcyclobutene, a product with a five-membered ring rather than a six-membered ring was obtained. (C) 2002 Elsevier Science B.V. All rights reserved.
• DIFRANCESCO D.; PINHAS A. R., J. ORG. CHEM., 51,(1986) N 11, 2098-2102
  作者：DIFRANCESCO D.、 PINHAS A. R.

  DOI：——

  日期：——