5-溴呋喃-2(5H)-酮 | 40125-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 5-溴呋喃-2(5H)-酮
• 中文别名: 5-溴-呋喃-2(5H)-酮
• 英文名称: 5-bromo-2(5H)-furanone
• 英文别名: 5-bromo-furan-2(5H)-one；2-bromo-5-oxo-2,5-dihydrofuran；5-Bromofuran-2(5H)-one；2-bromo-2H-furan-5-one
• CAS: 40125-53-9
• 化学式: C₄H₃BrO₂
• 分子量: 162.971
• InChiKey: ODQLAECNMKXOBI-UHFFFAOYSA-N

物化性质

• 沸点：
  101-102 °C(Press: 10 Torr)
• 密度：
  1.9402 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  5-溴呋喃-2(5H)-酮 、 Penicillin G potassium 生成 6β-(2-phenyl-acetylamino)-penicillanic acid (Ξ)-5-oxo-2,5-dihydro-furan-2-yl ester
  参考文献：
  名称：

  Preparation, hydrolysis, and oral absorption of lactonyl esters of penicillins

  摘要：

  Lactonyl esters of ampicillin and other penicillins have been synthesized as prodrugs designed to improve the oral absorption of the parent penicillins. In general, the esters hydrolyzed rapidly in the presence of tissues including blood and certain of the esters were better absorbed than the parent penicillin. The phthalidyl ester of ampicillin [talampicillin (British Pharmacopoeia approved name), BRL 8988] was selected for extended studies. The compound was found to be well absorbed in various animal species and gave ampicillin serum concentrations in fasting human volunteers 2.5-3 times those obtained for ampicillin itself.

  DOI：

  10.1021/jm00234a007
• 作为产物：
  描述：

  2(5H)-呋喃酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 生成 5-溴呋喃-2(5H)-酮
  参考文献：
  名称：

  Aflatoxins Revisited: Convergent Synthesis of the ABC-Moiety

  摘要：

  在进行了适当的模型研究后，针对黄曲霉毒素 B1 的含氧 ABC 分子的聚合合成，对目前备受关注的两种制备方法，即自由基引发的 5-exo-trig 环化和钯/甲酸根阴离子介导的分子内加氢反应进行了探讨和优化。

  DOI：

  10.1055/s-1988-27700

文献信息

• Aryl radical-induced cyclization routes to furo[2,3-b]benzofurans. Abbreviated formal syntheses of aflatoxins B1 and B2
  作者：C.P. Sloan、J.C. Cuevas、C. Quesnelle、V. Snieckuss

  DOI：10.1016/s0040-4039(00)80580-8

  日期：——

  Radical-induced cyclization of butenolide ethers 3a-c affords furobenzofurans 4a-c; deprotection of 4c gives 4d, thus concluding formal total syntheses of aflatoxins B1 (5) and B2 (6).

  自由基诱导的丁烯醚醚3a - c的环化反应生成呋喃苯并呋喃4a - c；4c脱保护得到4d，因此得出黄曲霉毒素B 1（5）和B 2（6）的正式总合成。
• Chiral Bicyclic Imidazole‐Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters
  作者：Muxing Zhou、Tatiana Gridneva、Zhenfeng Zhang、Ende He、Yangang Liu、Wanbin Zhang

  DOI：10.1002/anie.202012445

  日期：2021.1.18

  Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3‐hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely

  利用手性双环咪唑有机催化剂并采用连续注射工艺，已开发出另一种途径，可通过对映选择性酰化作用（3-99％ee）动态动力学拆分3-羟基邻苯二酚来有效合成手性邻苯二甲酸酯基前药。计算研究表明，一般的基础催化机理不同于广泛接受的亲核催化机理。关键过渡态的结构分析表明，催化剂与底物之间的CH-π相互作用而不是先前考虑的阳离子/π-π相互作用是引起观察到的立体控制的主要因素。
• Lactol esters of ampicillin.
  作者：ICHIRO ISAKA、KOHZI NAKANO、TERUYA KASHIWAGI、AKIO KODA、HIROSHI HORIGUCHI、HIDEFUMI MATSUI、KOZO TAKAHASHI、MASUO MURAKAMI

  DOI：10.1248/cpb.24.102

  日期：——

  Several lactol esters of D-α-aminobenzylpenicillin hydrochloride (Va-e) were synthesized from the corresponding lactol esters of benzylpenicillin (IIa-e) or from D-α-aminobenzylpenicillin (ampicillin). The lactol esters IIa-e were prepared with potassium benzylpenicillinate (I) and certain halides of lactols. Among them, two isomers of 2 (5H)-furanone-5-yl benzylpenicillinate (IIb) could be easily separated from the mixture of the stereoisomers due to C5' position of the lactol moiety. We found that all of these lactol esters of ampicillin hydrochloride (Va-e) showed higher blood concentrations of ampicillin after oral administration to rats than that of ampicillin itself. Particularly Va and Ve were much superior.

  几种D-α-氨基苄青霉素盐酸盐的乳醇酯（Va-e）是通过相应的苄青霉素（IIa-e）乳醇酯或D-α-氨基苄青霉素（氨苄青霉素）合成的。乳醇酯IIa-e是采用苄青霉素钾盐（I）和某些乳醇的卤化物制备的。在这些化合物中，由于乳醇部分的C5'位，两个2（5H）-呋喃酮-5-基苄青霉酸盐（IIb）的异构体能够很容易地从立体异构体的混合物中分离出来。我们发现，在口服给药后，这些氨苄青霉素盐酸盐的乳醇酯（Va-e）在大鼠体内的血药浓度均高于氨苄青霉素本身，特别是Va和Ve表现得更为优越。
• Bisketene Equivalents as Diels–Alder Dienes
  作者：Isuru Dissanayake、Jacob D. Hart、Emma C. Becroft、Christopher J. Sumby、Christopher G. Newton

  DOI：10.1021/jacs.0c06306

  日期：2020.8.5

  5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from

  2,5-双（叔丁基二甲基甲硅烷氧基）呋喃被确定为邻位双烯酮等价物，用于在 Diels-Alder 反应中用作二烯。在非常温和的条件下，与烯烃亲二烯体的环加成能够通过一锅 Diels-Alder/开环/互变异构化序列以未保护的形式聚合获得高度取代的对氢醌。还展示了从乙炔亲二烯体（包括苄）合成对苯醌，并且将 2,5-双（叔丁基二甲基甲硅烷氧基）吡咯确定为合成对亚氨基醌的有效二烯。在天然产物合成中的应用能够实现克级规模的神经保护剂 (±)-indanostatin。
• Facile synthesis of 4-substituted butenolides from furan
  作者：Tatsuya Shono、Yoshihiro Matsumura、Shin-ichiro Yamane

  DOI：10.1016/s0040-4039(01)81881-5

  日期：1981.1

  A variety of 4-substituted butenolides were prepared utilizing 2-acetoxyfuran as a key intermediate which can be easily synthesized by anodic oxidation of furan.

  利用2-乙酰氧基呋喃作为关键中间体制备了多种4-取代的丁烯内酯，这些中间体很容易通过呋喃的阳极氧化而合成。