2-甲基-5-丙基环己-2,5-二烯-1,4-二酮 | 65644-50-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基-5-丙基环己-2,5-二烯-1,4-二酮
• 英文名称: 2-methyl-5-propyl-1,4-benzoquinone
• 英文别名: 2-n-Propyl-5-methylbenzoquinone；2-methyl-5-propyl-[1,4]benzoquinone；1-Methyl-4-propyl-cyclohexadien-(1.4)-dion-(3.6)；2-Methyl-5-propyl-[1,4]benzochinon；2,5-Cyclohexadiene-1,4-dione, 2-methyl-5-propyl-；2-methyl-5-propylcyclohexa-2,5-diene-1,4-dione
• CAS: 65644-50-0
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: VLVGZKXVZLAHAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基-5-丙基环己-2,5-二烯-1,4-二酮 生成 Dithymochinon
  参考文献：
  名称：

  El-Dakhakhny,M., Justus Liebigs Annalen der Chemie, 1965, vol. 685, p. 134 - 139

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(Dimethylamino)-5-methyl-2-propylphenol 在 ammonium cerium(IV) nitrate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-甲基-5-丙基环己-2,5-二烯-1,4-二酮
  参考文献：
  名称：

  Phenol Formation from the Reactions of Amino-Stabilized Alkenyl Fischer Carbene Complexes

  摘要：

  The first examples of phenol formation from the reactions of amino-stabilized alpha,beta P-unsaturated Fischer carbene complexes with alkynes are reported. A series of four dimethylamino complexes [(CO)(5)Cr=C(NMe(2))R; 19, R = cyclohexenyl; 26, R = trans-propenyl; 27, R = trans-styryl; 30, R = isopropenyl] were examined with both internal and external alkynes. Their reactions with internal alkynes typically produced low yields of complex mixtures of products and were not synthetically useful. In contrast, their reactions with terminal alkynes were remarkably different giving good yields of 4-(dimethylamino)phenols, and in the presence of a trapping agent, good yields of the arene chromium tricarbonyl complexes of the protected 4-(dimethylamino)phenols. The selectivity for phenol formation was found to be greatest for reactions performed in noncoordinating solvents and at higher concentrations. In contrast, and as expected, the reaction of the aryl complex 45 [(CO)(5)Cr=C(NMe(2))Ph] with 1-pentyne did not produce any six-membered ring product in DMF, THF, or benzene. An interesting solvent dependence was observed for this reaction where lactam 49 was the exclusive product in benzene and the indanone 46 was the exclusive product in DMF.

  DOI：

  10.1021/jo00119a039

文献信息

• Direct preparation of differentially protected hydroquinone-chromium(tricarbonyl) complexes from the benzannulation reaction of fischer carbene complexes
  作者：Steven Chamberlin、William D. Wulff、Brian Bax

  DOI：10.1016/s0040-4020(01)87267-7

  日期：1993.1

  hydroquinone-chromium(tricarbonyl) complexes directly from alkenyl Fischer carbene complexes and alkynes are described. The benzannulation reaction of methoxy carbene complexes with alkynes produces hydroquinone chromium tricarbonyl complexes as their mono-methyl ethers which may be protected at the free aryl hydroxyl with either sequential or concurrent reaction with a variety of electrophiles, including silyl chlorides

  描述了直接从烯基菲舍尔卡宾配合物和炔烃制备差异保护的氢醌-铬（三羰基）配合物的方法。甲氧基卡宾配合物与炔烃的苯环合反应生成氢醌铬三羰基配合物，作为它们的单甲基醚，可以在​​游离芳基羟基上得到保护，并与各种亲电试剂依次或同时反应，包括甲硅烷基氯和三氟甲磺酸酯，酰基和烷基卤化物和酸酐。芳烃配合物获得的产率等于或超过从相同的苯环化反应分离出的苯酚或醌产物的产率，其中三羰基铬已从芳烃氧化释放出来。β-甲硅烷基-烯基配合物与炔烃的反应也可以直接获得差异保护的配合物。这些方法不适用于由芳基卡宾配合物与炔烃的反应制备差异保护的萘并氢醌铬三羰基配合物。
• Cross-Linking and Sequence-Specific Alkylation of DNA by Aziridinylquinones. 3. Effects of Alkyl Substituents
  作者：Robert H. J. Hargreaves、C. Caroline O'Hare、John A. Hartley、David Ross、John Butler

  DOI：10.1021/jm991007y

  日期：1999.6.1

  cytotoxicities and DNA cross-linking abilities of several alkyl-substituted diaziridinylquinones have been investigated. The cytotoxicities were determined in DT-diaphorase-rich (H460 and HT29) and -deficient (H596 and BE) cell lines. It was shown that the cytotoxicities in these cell lines correlated with the relative rates of reduction by the purified human enzyme and with the cross-linking efficiencies.

  已经研究了几种烷基取代的二叠氮基奎宁醌的细胞毒性和DNA交联能力。在富含DT-黄递酶的细胞（H460和HT29）和细胞缺陷（H596和BE）的细胞系中测定细胞毒性。结果表明，这些细胞系中的细胞毒性与纯化的人酶的相对还原速率以及交联效率相关。通过循环伏安法测定，DT-心肌黄递酶的还原速率比还原电位更依赖于化合物的结构。还使用计算机模型来解释高效率的交联和还原的甲基取代的二叠氮基奎宁酮的GNC序列选择性。
• Benzannulation of .alpha.,.beta.-unsaturated Fischer carbene complexes with acetylenes
  作者：William D. Wulff、Kin Shing Chan、Peng Cho Tang

  DOI：10.1021/jo00186a046

  日期：1984.6
• Bayrac, Bulletin de la Societe Chimique de France, 1895, vol. <3> 13, p. 979
  作者：Bayrac

  DOI：——

  日期：——
• Contrasteric Regiochemical Incorporation of Stannylacetylenes in the Benzannulation Reaction
  作者：Steven Chamberlin、Marcey L. Waters、William D. Wulff

  DOI：10.1021/ja00086a047

  日期：1994.4