3,4-二亚甲基环丁-1-烯 | 5291-90-7

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 3,4-二亚甲基环丁-1-烯
• 英文名称: 3,4-dimethylenecyclobutene
• 英文别名: 3,4-Dimethylencyclobuten；3,4-Bis(methylen)cyclobuten；1,2-Dimethylencyclobuten；Dimethylencyclobuten；3,4-Dimethylenecyclobut-1-ene；3,4-dimethylidenecyclobutene
• CAS: 5291-90-7
• 化学式: C₆H₆
• 分子量: 78.1136
• InChiKey: WHCRVRGGFVUMOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902199090

反应信息

• 作为反应物：
  描述：

  3,4-二亚甲基环丁-1-烯 以 二氯甲烷 、 甲苯 为溶剂， 生成 (1S,2S,5R,14S,17R,18R)-1,18-diphenyl-25-oxaheptacyclo[16.6.1.02,17.03,16.05,14.07,12.019,24]pentacosa-3(16),7,9,11,19,21,23-heptaene-6,13-dione
  参考文献：
  名称：

  含苯齐并苯的合成及光学性质

  摘要：

  描述了使用 3,4-双 (亚甲基) 环丁烯作为连续 Diels-Alder 反应的构建单元合成一类新的完全不饱和梯形结构，即含亚苯基的低聚并苯 (POA)。通过所报道化合物的光学和电化学性质，可以观察到抗芳香性的应变和能量成本的几何效应。由此产生的形状持久梯形结构包含相邻的发色团，这些发色团彼此部分电子隔离，同时仍会降低材料的带隙。

  DOI：

  10.1021/ja3043883
• 作为产物：
  描述：

  1,5-己二炔 506.85 ℃ 、2.5 MPa 条件下， 生成 3,4-二亚甲基环丁-1-烯
  参考文献：
  名称：

  1,5-己二炔在宽温度和压力范围内热重排的激波管研究

  摘要：

  已经在高压单脉冲激波管中研究了 1,5-己二炔的热解，以研究从炔丙基自由基生产苯的机制。通过气相色谱和基质分离傅里叶变换红外光谱对反应产物的分析已明确鉴定出六种线性 C6H6 物质和两种环状 C6H6 物质。在这些物种中，cis-1,3-hexadien-5-yne 和 trans-1,3-hexadiene-5-yne 首次被明确鉴定，并提供了关于低温苯的重要信息，但不涉及富烯的形成；然而，这些数据也为从炔丙基自由基通过富烯到苯的两条高温路径提供了支持。因此，已经获得了支持两种不同的苯形成途径的实验证据。

  DOI：

  10.1021/jp037310z

文献信息

• Kaupp, Gerd; Grueter, Heinz-Willi; Teufel, Eberhard, Chemische Berichte, 1983, vol. 116, # 2, p. 618 - 629
  作者：Kaupp, Gerd、Grueter, Heinz-Willi、Teufel, Eberhard

  DOI：——

  日期：——
• Pressure and Temperature Effects on Product Channels of the Propargyl (HC⋮CCH₂) Combination Reaction and the Formation of the “First Ring”
  作者：Pui-Teng Howe、Askar Fahr

  DOI：10.1021/jp0307497

  日期：2003.11.1

  The propargyl (HCequivalent toC-CH2) radical is among the critical intermediates in hydrocarbon reaction systems pertinent to both the high temperatures of combustion systems and the low temperatures of planetary atmospheres. This work reports experimental results on the nature and the relative yields of the final products of the propargyl combination reaction, C3H3 + C3H3 --> C6H6 (1). Propargyl radicals, for most experiments, were generated by the 248 nm excimer laser photolysis of propargyl bromide. The 193 nm photolysis of propargyl chloride and of allene were also used in a number of experiments, particularly at higher temperatures. Product studies were performed at a pressure range of 27 mbar (20 Torr) to 933 mbar (700 Torr) and at a temperature range of 295-623 K. Final reaction products were separated, identified, and quantified using an on-line gas chromatograph/mass spectrometer system. Five isomeric C6H6 final products were detected including 1,5-hexadiyne, fulvene, dimethylenecyclobutene, and benzene. The relative yields of the major reaction products showed significant pressure and temperature dependencies. Under high-pressure conditions 1,5-hexadiyne is a major product with a relative yield of 51 % at P = 933 mbar and T = 295 K. However, its yield decreases to 27 % at P = 933 mbar and T = 623 K and to 1 % at P = 27 mbar, T = 623 K. Dimethylenecyclobutene, has a relative yield of 6% at 295 K and 933 mbar. It becomes the most abundant product with a relative yield of nearly 90% at 623 K and 133 mbar. Fulvene appears to be a minor product at all conditions of this study and its relative yield (similar to1.5% or less) is significantly lower than the reported computational predictions. Interestingly, an appreciable amount of benzene is also formed, particularly at lower pressures with relative yields considerably higher (43% at 27 mbar and 623 K) than those predicted computationally (similar to3% at P = 27 mbar T = 650 K). The results of this work suggest that the formation of dimethylenecyclobutene and benzene from the propargyl combination reaction is significantly more efficient than previously predicted. Implications of these results on modeling of combustion processes as well as planetary atmospheric processes are discussed.
• The Thermal Rearrangement of 1,5-Hexadiyne and Related Compounds
  作者：William D. Huntsman、Harry J. Wristers

  DOI：10.1021/ja00978a030

  日期：1967.1
• Thermischer Ringschluss substituierter buta-1,3-diene
  作者：H.A. Brune、W. Schwab

  DOI：10.1016/s0040-4020(01)82977-x

  日期：1969.1
• Rau, Doris; Behrens, Ulrich, Angewandte Chemie, 1991, vol. 103, p. 847 - 848
  作者：Rau, Doris、Behrens, Ulrich

  DOI：——

  日期：——