3-acetyl-1-(4'-methylphenyl)-2-pentene-1,4-dione | 89201-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-acetyl-1-(4'-methylphenyl)-2-pentene-1,4-dione
• 英文别名: 3-Acetyl-1-(4-methylphenyl)pent-2-ene-1,4-dione
• CAS: 89201-21-8
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: GQNGZCRKNYAHDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetyl-1-(4'-methylphenyl)-2-pentene-1,4-dione 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 4-(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-(4'-methylphenyl)-2-methylfuran
  参考文献：
  名称：

  Synthesis of polyfunctionalized furans from 3-acetyl-1-aryl-2-pentene-1,4-diones

  摘要：

  The BF3-catalyzed cyclization of 3-acetyl-1-aryl-2-pentene-1,4-diones 1a-e in the presence of water in boiling tetrahydrofuran gave bis(3-acetyl-5-aryl-2-furyl)methanes 2a-e in 26-79% yields along with a small amount of 3-acetyl-5-aryl-2-methylfurans 3a-e. The exact structure of 2a was determined by X-ray crystallography. The use of a half volume of the solvent for the reaction of la resulted in the formation of 2,4-bis(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-phenylfuran (4) together with 2a and 3a. A similar reaction of la was carried out in the presence of 3-acetyl-5-(4-methylphenyl)-2-methylfuran (3d) to afford 4-(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-(4methylphenyl)-2-methylfuran (5) in 49% yield. The BF3-catalyzed reaction of la with 2,4-pentanedione in dry tetrahydrofuran at 23degreesC gave 3-(3-acetyl-5-phenyl-2-furfuryl)-4-hydroxy-3-penten-2-one (6a) and 3-(3-acetyl-2-methyl-4-phenyl-5-furyl)-4-hydroxy-3-penten-2one (7a) in 66 and 24% yields, respectively. The product distribution depended on the reaction temperature. A similar reaction of 1b-e also yielded the corresponding trisubstituted furans 6b-e and tetrasubstituted furans 7b-e in good yields. These results suggested the presence of the furfuryl carbocation intermediate A during the reaction. The one-pot synthesis of 6a and 7a was also achieved by a similar reaction using phenylglyoxal. The deoxygenation of la with triphenylphosphine gave 3a in 88% yield, while la was treated with concentrated hydrochloric acid to yield 3-acetyl-2-chloromethyl-5-phenylfuran (8) which was quantitatively transformed in ethanol into 3-acetyl-2-ethoxymethyl-5phenylfuran (9) and in water into 3-acetyl-5-phenylfurfuryl alcohol (10), respectively. In addition, the Diels-Alder reaction of cyclopantadiene with 1a gave the corresponding [4+2] cycloaddition products 11 and 12. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01597-1
• 作为产物：
  描述：

  1-(4-甲基苯基)-1,2-丙二酮 在 selenium(IV) oxide 作用下， 生成 3-acetyl-1-(4'-methylphenyl)-2-pentene-1,4-dione
  参考文献：
  名称：

  环己基异氰化物、乙炔二羧酸二烷基酯和 1-芳基-2-烯-3-乙酰-1,4-二酮之间的反应。一锅法合成高度官能化的 5-环己基亚氨基-2,5-二氢呋喃

  摘要：

  二氢呋喃是有机合成中的重要中间体，也是合成多种天然产物的重要原料。描述了通过环己基异氰化物、乙炔二羧酸二烷基酯和 1-芳基-2-烯-3-乙酰-1,4-二酮的多组分反应轻松合成高度官能化的 5cyclohexylimino-2,5-dihydrofuran 衍生物。

  DOI：

  10.24820/ark.5550190.p010.628

文献信息

• 2-Indolymethanols as 4-atom-synthons in oxa-Michael reaction cascade: access to tetracyclic indoles
  作者：Tian-Jiao Han、Min-Can Wang、Guang-Jian Mei

  DOI：10.1039/d1cc03653j

  日期：——

  The first Brønsted acid-catalyzed oxa-Michael reaction cascade of 2-indolylmethanols with trione alkenes was accomplished. By using this practical approach, a variety of tetracyclic indoles were readily created in an ordered sequence with excellent regio- and diastereoselectivity. 2-Indolylmethanols commendably served as four-atom synthons, as opposed to the common three-atom synthons in the previous

  第一个 Brønsted 酸催化的 2-吲哚甲醇与三酮烯烃的 oxa-Michael 反应级联完成。通过使用这种实用的方法，可以很容易地以有序的顺序创建各种四环吲哚，并具有出色的区域选择性和非对映选择性。与之前文献报道中常见的三原子合成子不同，2-吲哚甲醇作为四原子合成子值得称赞。通过使用强布朗斯台德酸催化剂，区域选择性问题得到了很好的处理。此外，提出了它通过氢键相互作用激活底物和加速随后的分子内环化和脱水的双重作用，以解释高反应效率。
• Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes
  作者：Mingyue Wu、Zhaobin Han、Huanzhen Ni、Nengzhong Wang、Kuiling Ding、Yixin Lu

  DOI：10.1039/d1sc06364b

  日期：——

  Highly enantioselective and chemodivergent domino reactions between γ-substituted allenoates and activated alkenes have been developed.

  已经开发出高度对映选择性和化学多样性的多米诺反应，该反应涉及γ取代的烯酸酯和活性烯烃之间的反应。
• Acid-catalyzed convenient transformation of 1-aryl-2-pentene-1,4-diones into polyfunctionalized furans
  作者：Satoaki Onitsuka、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1016/s0040-4039(00)00373-7

  日期：2000.4

  of boron trifluoride gave the unstable 3-acetyl-1-phenyl-2-pentene-1,4-dione intermediate which was converted in situ by the reaction with an excess amount of 2,4-pentanedione into new crystalline tri- and tetra-substituted furans. Other unstable 1-aryl-2-pentene-1,4-diones, which were obtained by the photooxygenation of 3-acetyl-5-aryl-2-methylfurans, were trapped by the acid-catalyzed reaction, giving

  苯乙二醛与2,4-戊二酮在三氟化硼的存在下反应，生成了不稳定的3-乙酰基-1-苯基-2-戊烯-1,4-二酮中间体，该中间体通过反应与过量的三氟甲磺酸原位转化。 2,4-戊二酮变成新的结晶的三取代和四取代的呋喃。通过3-乙酰基-5-芳基-2-甲基呋喃的光氧化作用获得的其他不稳定的1-芳基-2-戊烯-1,4-二酮不稳定，通过酸催化反应被捕获，从而以高收率得到多官能化的呋喃。用浓盐酸处理1-苯基-2-戊烯-1，4-二酮中间体，然后将乙醇煮沸，通过不稳定的2-氯甲基呋喃定量产生稳定的2-乙氧基甲基呋喃。
• Catalyst-free racemic and H₂O/CPA-catalyzed asymmetric regio-reversed domino processes of triketone enones with azlactones
  作者：Yun-Dong Fu、Xiang Gao、Shi-Kun Jia、Xiao Xiao、Min-Can Wang、Lihua Huang、Guang-Jian Mei

  DOI：10.1039/d3gc01445b

  日期：——

  Regio-reversed domino processes of triketone enones with azlactones have been established. Opposite to the previous β-addition-triggered domino processes, this protocol is initiated by a regio-reversed α-addition. Under catalyst-free conditions, the domino reaction readily occurred, leading to the formation of a variety of bicyclic furofurans bearing vicinal quaternary carbons in good to excellent

  三酮烯酮与吖内酯的区域反转多米诺骨牌过程已经建立。与之前的 β 加法触发的多米诺骨牌过程相反，该协议是由区域反转 α 加法启动的。在无催化剂条件下，容易发生多米诺骨牌反应，从而以良好至优异的产率形成多种带有邻位季碳的双环呋喃呋喃。此外，使用手性磷酸催化实现了催化不对称版本，其中H 2 O在对映体控制中发挥了关键作用。值得注意的是，所有制备的对映体富集产物都可以进一步重结晶，以确保优异的对映选择性。
• Diastereodivergent and Regioselective Synthesis of Tetrahydrofuro[2,3-<i>b</i>]furans with Four Consecutive Stereocenters
  作者：Jing Zhang、Wen-Na Sun、Zhiwei Jiang、Shi-Kun Jia、Guang-Jian Mei

  DOI：10.1021/acs.joc.4c00069

  日期：2024.3.15

  Base-catalyzed diastereodivergent and regioselective domino processes of triketone enones with arylacetaldehydes for the synthesis of tetrahydrofuro[2,3-b]furans with four consecutive stereocenters are reported. Good yields and diastereoselectivities are obtained when DBU is employed as a catalyst; in contrast, Et3N delivers a different diastereomer in excellent diastereoselectivity. This work offers

  报道了三酮烯酮与芳基乙醛的碱催化非对映发散和区域​​选择性多米诺过程，用于合成具有四个连续立体中心的四氢呋喃并[2,3- b ]呋喃。使用DBU作为催化剂可以获得良好的产率和非对映选择性；相比之下，Et 3 N 则以优异的非对映选择性提供不同的非对映异构体。这项工作具有许多优点，包括可切换的非对映选择性、廉价的碱性催化剂和简单的操作。