1-(furan-2-yl)but-3-en-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(furan-2-yl)but-3-en-1-one
• 英文别名: Allyl 2-furyl ketone
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: INHOSYWZGAASRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(furan-2-yl)but-3-en-1-one 在 potassium osmate 、 sodium periodate 、 三(N,N-四亚甲基)磷酰胺 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 caesium carbonate 、 N-甲基吗啉氧化物 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 对苯二酚 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲基叔丁基醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 68.23h， 生成 isopropyl (Z)-7-(3-hydroxy-5-oxo-cyclopent-1-en-1-yl)-hept-5-enoate
  参考文献：
  名称：

  合成前列腺素类似物的手性4-甲硅烷基环戊烯酮中间体的制备

  摘要：

  A process is described for the synthesis of kilogram quantities of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for the synthesis of a plurality of prostaglandin analogue drugs. Cyclopentenone (R)-1 was synthesized in 14 isolated steps from furfural. Key steps in the synthesis include a Wittig reaction, Piancatelli rearrangement, and an enzymatic resolution featuring in situ

  DOI：

  10.1021/op300188x
• 作为产物：
  描述：

  2-糠醛缩二乙醇 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 甲苯 为溶剂， 反应 4.03h， 生成 1-(furan-2-yl)but-3-en-1-one
  参考文献：
  名称：

  Benzotriazole-Mediated Conversions of Aromatic and Heteroaromatic Aldehydes to Functionalized Ketones

  摘要：

  Aromatic and heteroaromatic aldehydes reacted with benzotriazole and triethyl orthoformate in THF to give the corresponding alpha-(benzotriazol-1-yl)aryl ethyl ethers 7 in good yield. The novel acyl anion precursors 7 underwent smooth lithiation at the methine group followed by trapping with alkyl halides, aldehydes, ketones, and imines to yield the expected substituted intermediates of type 9, which were hydrolyzed under mild conditions without isolation. Benzaldehyde, methyl-, chloro-, and methoxy-substituted benzaldehydes, 1-naphthalenecarboxaldehyde, 2- and 3-furaldehydes, 2- and 3-thiophenecarboxaldehydes, and 2-pyridinecarboxaldehyde were all transformed in this manner into a variety of aryl and heteroaryl ketones with alkyl (10), alpha-hydroxyalkyl (12 and 13), alpha-aminoalkyl (14) and acyl(15) substituents.

  DOI：

  10.1021/jo00128a039

文献信息

• Copper-Catalyzed Aerobic Cyclization of β,γ-Unsaturated Hydrazones with Concomitant C═C Bond Cleavage
  作者：Zhenwei Fan、Jiahao Feng、Yuchen Hou、Min Rao、Jiajia Cheng

  DOI：10.1021/acs.orglett.0c02911

  日期：2020.10.16

  aerobic oxidative cyclization of β,γ-unsaturated hydrazones for the preparation of pyrazole derivatives has been developed. The hydrazonyl radical promoted the cyclization, along with a concomitant C═C bond cleavage of β,γ-unsaturated hydrazones. This process has been verified via several control experiments, including a radical-trapping study, an 18O-labeling method, and the identification of the possible

  已经开发出Cu催化的β，γ-不饱和的需氧氧化环化反应，用于制备吡唑衍生物。肼基自由基促进了环化，并伴随着β，γ-不饱和的C═C键裂解。该过程已通过一些对照实验进行了验证，包括自由基捕获研究，18 O标记方法以及可能副产物的鉴定。该反应的优点包括操作简单，反应范围宽和温和的选择性反应过程。
• Process for the preparation of 2-furyl-n-pentylketone and longer chain analogs
  申请人：Passaro C. Linda

  公开号：US20060094888A1

  公开（公告）日：2006-05-04

  A process of making furfural-derived ketones is disclosed. These compounds may be useful as marine antifouling agents. The process uses the steps of: reacting a furfural with 1,3-dithiopropane to form a 1,3-dithiane derivative; metalizing the 1,3-dithiane derivative to form a metalodithiane derivative; reacting the metalodithiane derivative with a halide or pseudohalide to form a ketone precursor; and hydrolyzing the ketone precursor to form a furyl ketone.

  披露了一种由糠醛衍生酮的制造过程。这些化合物可能作为海洋防污剂是有用的。该过程包括以下步骤：将糠醛与1,3-二硫代丙烷反应，形成1,3-二硫代烷衍生物；将1,3-二硫代烷衍生物金属化，形成金属二硫代烷衍生物；将金属二硫代烷衍生物与卤素或拟卤素反应，形成酮前体；以及将酮前体水解，形成 furyl 酮。
• Synthesis of β,γ-Unsaturated Ketones from Acid Chlorides through Carbon–Pentamethylcyclopentadienyl Bond Formation and Cleavage
  作者：Minoru Uemura、Masayuki Iwasaki、Eiji Morita、Hideki Yorimitsu、Koichiro Oshima

  DOI：10.1246/bcsj.80.2400

  日期：2007.12.15

  Reaction of acid chlorides with lithium pentamethylcyclopentadienide afforded the corresponding pentamethyl-cyclopentadienyl ketones in high yield. These ketones were treated with an allylaluminum reagent to form the corresponding 3-butenyl alcohols. Removal of pentamethylcyclopentadiene upon heating or treatment with a catalytic amount of trichloroacetic acid yielded the corresponding β,γ-unsaturated

  酰氯与五甲基环戊二烯锂反应以高产率得到相应的五甲基-环戊二烯基酮。这些酮用烯丙基铝试剂处理以形成相应的3-丁烯醇。在加热或用催化量的三氯乙酸处理后去除五甲基环戊二烯，以良好的产率得到相应的 β,γ-不饱和酮。
• Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems
  作者：Roman Kleinmans、Omar Apolinar、Joseph Derosa、Malkanthi K. Karunananda、Zi-Qi Li、Van T. Tran、Steven R. Wisniewski、Keary M. Engle

  DOI：10.1021/acs.orglett.1c01447

  日期：2021.7.16

  2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding

  报道了镍催化的烯基酮与芳基碘化物和芳基硼​​酸酯的 1,2-二芳基化反应。具有多种取代基的酮可作为有效的导向基团，提供高水平的区域控制。代表性产品被多样化为各种有用的产品，这些产品不容易通过现有的 1,2-二芳基化反应获得。初步机理研究揭示了底物的结合模式，哈米特分析揭示了电子因素对初始速率的影响。
• Copper-Promoted 6-<i>endo-trig</i> Cyclization of β,γ-Unsaturated Hydrazones for the Synthesis of 1,6-Dihydropyridazines
  作者：Yong-Qiang Guo、Mi-Na Zhao、Zhi-Hui Ren、Zheng-Hui Guan

  DOI：10.1021/acs.orglett.8b01240

  日期：2018.6.1

  A novel and efficient strategy for the synthesis of 1,6-dihydropyridazines via copper-promoted 6-endo-trig cyclization of readily available β,γ-unsaturated hydrazones have been developed. A series of 1,6-dihydropyridazines have been synthesized by this method with good yields, high functional group tolerance, and remarkable regioselectivity under mild conditions. Importantly, the 1,6-dihydropyridazines

  已经开发了通过铜促进的6 - β-内-trig环化容易获得的β，γ-不饱和酮合成1,6-二氢哒嗪的新颖而有效的策略。通过该方法合成了一系列1,6-二氢哒嗪，具有良好的收率，较高的官能团耐受性以及在温和条件下的显着区域选择性。重要的是，在NaOH的存在下，可以将1，6-二氢哒嗪有效地转化为生物学上重要的哒嗪。