1,5-bis-(4-isopropyl-phenyl)-penta-1,4-dien-3-one | 71492-41-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,5-bis-(4-isopropyl-phenyl)-penta-1,4-dien-3-one
• 英文别名: γ-Oxo-α.ε-bis-(4-isopropyl-phenyl)-α.δ-pentadien；γ-Oxo-α.ε-dicumyl-α.δ-pentadien；1,5-Bis-(4-isopropyl-phenyl)-penta-1,4-dien-3-on；Dicuminylidenaceton；Dicuminalaceton；1,5-Bis-(p-isopropylphenyl)-1,4-pentadien-3-on；1,5-Bis(4-isopropylphenyl)-1,4-pentadien-3-one；1,5-bis(4-propan-2-ylphenyl)penta-1,4-dien-3-one
• CAS: 71492-41-6
• 化学式: C₂₃H₂₆O
• 分子量: 318.459
• InChiKey: YPEKVBHDIMZUOU-UHFFFAOYSA-N

物化性质

• 沸点：
  462.8±34.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5-bis-(4-isopropyl-phenyl)-penta-1,4-dien-3-one 在 镍 氢气 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 1,5-bis<4-(1-methylethyl)-phenyl>-3-pentanone
  参考文献：
  名称：

  Antibacterial N-[.omega.,.omega.'-bis(alicyclic and aryl)-sec-alkyl]poly(methylenetriamine and -tetramine) hydrochloride salts

  摘要：

  A series of antibacterial N-(omega, omega'-(cycloalkyl, bicyclo[2.2.1]heptyl, and alkyl-substituted phenyl)-sec-alkyl]poly(methylene)triamine and -tetramine hydrochloride salts were synthesized in an effort to develop efficient, nonsystemic inhibitors, particularly for Pseudomonas aeruginosa. In the 1,5,9-triazanonane group, 3 of 16 compounds were effective at 8--10 micrograms/mL against pseudomonads. Efficiency appeared more dependent upon lipophilicity of the nitrogen substituent than other characteristics represented by the three types of rings. A parabolic relationship was observed for the entire set between the hydrophobic parameter, pi, of the lipoidal moiety and minimal inhibitory concentration. One of 16 tetramines, 1-[1,5-bis(3,3-dimethyl-2-norbornyl)-3-pentyl]-1,5,9,13-tetraazatridecane tetrahydrochloride (26f), ranked similarly. An additional two compounds in each series were superior to several commercial cationic detergents in the control of the Gram-negative bacteria. None was inhibitory at up to 200 micrograms/mL for Proteus vulgaris.

  DOI：

  10.1021/jm00197a024
• 作为产物：
  描述：

  丙酮 、 4-异丙基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 1,5-bis-(4-isopropyl-phenyl)-penta-1,4-dien-3-one
  参考文献：
  名称：

  通过氮杂迈克尔加成/亲核加成/脱氢级联反应合成2-氨基-4-芳基-6-苯乙烯基嘧啶

  摘要：

  描述了一种通过各种二苯乙烯基酮与盐酸胍通过氮杂-迈克尔加成/亲核加成/脱氢级联过程反应合成2-氨基-4-芳基-6-苯乙烯基嘧啶的有效方法。该方案的显着特点是底物易得、无过渡金属体系、反应条件温和、原子经济性高、底物范围广、收率满意、后处理程序简单。

  DOI：

  10.1002/jhet.4731

文献信息

• Highly Enantioselective Synthesis of Spiro[cyclohexanone-oxindoles] and Spiro[cyclohexanone-pyrazolones] by Asymmetric Cascade [5+1] Double Michael Reactions
  作者：Bin Wu、Jian Chen、Mei-Qiu Li、Jin-Xin Zhang、Xiao-Ping Xu、Shun-Jun Ji、Xing-Wang Wang

  DOI：10.1002/ejoc.201101529

  日期：2012.3

  The asymmetric catalytic synthesis of naturally occurring and biologically active spiro compounds is a challenge for modern chemical methodology. Here we report the construction of spiro compounds through cascade [5+1] double Michael reactions between divinyl ketones and N-unprotectedoxindoles or N-phenyl-protected pyrazolones catalyzed by a combination of the easily available 9-amino-9-deoxy-epi-quinine

  天然存在和生物活性螺环化合物的不对称催化合成是现代化学方法的挑战。在这里，我们报告了通过二乙烯基酮和 N-未保护的羟吲哚或 N-苯基保护的吡唑啉酮之间的级联 [5+1] 双迈克尔反应构建螺环化合物，该反应由易于获得的 9-氨基-9-脱氧-表奎宁与 N-Boc-D-苯基甘氨酸。以高产率（高达 98%）和立体选择性（高达 >20:1 dr，99% ee）获得了所需的多立体螺环[环己酮-羟吲哚和 -吡唑啉酮]。
• Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones
  作者：Bin Wu、Guo-Gui Liu、Mei-Qiu Li、Yong Zhang、Shao-Yun Zhang、Jun-Ru Qiu、Xiao-Ping Xu、Shun-Jun Ji、Xing-Wang Wang

  DOI：10.1039/c0cc05418f

  日期：——

  Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3).

  硫脲改性的金鸡纳生物碱作为双功能催化剂和碱，可以通过两次迈克尔加成反应，用硝基甲烷催化二乙烯基酮的[5 + 1]逐步环化，从而提供了具有良好收率，优异的非对映选择性（> 20：1的旋光性4-硝基-环己酮）。 ）和高对映体比例（高达97：3）。
• Tri(<i>n</i>-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]
  作者：Hui Zheng、Ying Han、Jing Sun、Chao-Guo Yan

  DOI：10.3762/bjoc.18.68

  日期：——

  tri(n-butyl)phosphine-catalyzed reaction of isatylidene malononitriles and bis-chalcones in chloroform at 65 °C afforded functionalized spiro[cyclohexane-1,3'-indolines] in good yields and with good diastereoselectivity. On the other hand, the tri(n-butyl)phosphine-catalyzed reaction of 3-(ethoxycarbonylmethylene)oxindoles and bis-chalcones gave functionalized spiro[cyclohexane-1,3'-indolines] with

  三（正丁基）膦催化的异亚甲基丙二腈和双查耳酮在氯仿中在 65 °C 下的反应以良好的收率和良好的非对映选择性提供了官能化的螺[环己烷-1,3'-二氢吲哚]。另一方面，三(正丁基)膦催化的3-(乙氧基羰基亚甲基)吲哚和双查耳酮反应得到了具有不同区域选择性的功能化螺[环己烷-1,3'-二氢吲哚]。此外，三（正丁基）膦促进的多米诺环化反应的靛红和乙基异亚甲基氰基乙酸酯以令人满意的产率产生螺[indoline-3,2'-furan-3',3''-indolines]。
• Vorlaender; Hayakawa, Chemische Berichte, 1903, vol. 36, p. 3545
  作者：Vorlaender、Hayakawa

  DOI：——

  日期：——
• Claisen; Ponder, Justus Liebigs Annalen der Chemie, 1884, vol. 223, p. 147
  作者：Claisen、Ponder

  DOI：——

  日期：——