3-(phenyl-seleno)-2(5H)-furanone | 183488-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-(phenyl-seleno)-2(5H)-furanone
• 英文别名: 3-phenylselanylfuran-2(5H)-one；3-phenylselenyl-2(5H)-furanone；3-phenylselenylfuran-2(5H)-one；4-phenylselanyl-2H-furan-5-one
• CAS: 183488-93-9
• 化学式: C₁₀H₈O₂Se
• 分子量: 239.132
• InChiKey: UPJDQKATSWEILZ-UHFFFAOYSA-N

物化性质

• 沸点：
  404.1±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  lithium dimethylcuprate 、 3-(phenyl-seleno)-2(5H)-furanone 以 乙醚 为溶剂， 反应 0.17h， 以90%的产率得到(3S*,4R*)-4-methyl-3-phenylselanyl-γ-butyrolactone
  参考文献：
  名称：

  3-Phenylselanylfuran-2（5 H）-one：木酚素合成中的通用构建基块。3,4-二苄基γ-丁内酯的新方法

  摘要：

  现成的3-苯基硒基呋喃-2（5 H）-一通过有机铜试剂进行串联共轭加成-烷基化，以良好的收率和非对映选择性提供3,4-二取代的-3-苯基硒基-γ-丁内酯，可以将其转化为天然存在的化合物，例如木脂素。

  DOI：

  10.1016/s0040-4020(99)00721-8
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以63.4 mg的产率得到3-(phenyl-seleno)-2(5H)-furanone
  参考文献：
  名称：

  General, Regiodefined Access to α-Substituted Butenolides through Metal−Halogen Exchange of 3-Bromo-2-silyloxyfurans. Efficient Synthesis of an Anti-inflammatory Gorgonian Lipid

  摘要：

  A variety of alpha-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.

  DOI：

  10.1021/jo8015924

文献信息

• Preparation and palladium-catalysed cross-coupling reactions of 3- and 4-tributylstannylfuran-2(5H)-ones
  作者：Gregory J. Hollingworth、Gemma Perkins、Joseph Sweeney

  DOI：10.1039/p19960001913

  日期：——

  Stannylfuranones 1 and 2 were prepared by ipso radical desulfurative stannylation of phenylsulfanylfuranones 3 and 16. Compounds 1 and 2 underwent Stille coupling reactions with aryl iodides to give 3- and 4-arylfuran-2(5H)-ones.

  斯坦尼尔呋喃酮1和2是通过对苯巯基呋喃酮3和16进行亲电性脱硫锡化反应制备的。化合物1和2与芳基碘发生Stille偶联反应，生成3-和4-芳基取代的呋喃-2(5H)-酮。
• Efficient preparation of 3-substituted-furan-2(5H)-ones and their direct vinylogous aldol addition
  作者：Marco Bella、Giovanni Piancatelli、Antonella Squarcia

  DOI：10.1016/s0040-4020(01)00331-3

  日期：2001.5

  The deprotonation of 3-substituted-furan-2(5H)-ones 1, obtained via the hydrolysis of 3-substituted-2,5-dihydro-2,5-dimethoxyfurans, affords in the reaction with both aromatic and aliphatic aldehydes regioselectively the unsaturated 3-substituted 5-(1′-hydroxy)-γ-butyrolactones, such as 4, 5, 6, 7, 8, 9 and 10. The use of Lewis acids allows modulation of the diastereoisomeric ratios. The subsequent

  通过3-取代的2,5-二氢-2,5-二甲氧基呋喃的水解反应获得的3-取代的呋喃-2（5 H）-ones 1的去质子化可选择性地与芳族和脂族醛进行反应不饱和的3-取代的-5-（1'-羟基） - γ丁内酯，如4，5，6，7，8，9和10。路易斯酸的使用允许非对映异构体比例的调节。随后用硼化镍进行的还原导致形成相应的饱和5-（1'-羟基）-γ-丁内酯，例如11，12和13。
• Direct vinylogous aldol addition of γ-butyrolactones and γ-butyrolactams
  作者：Marco Bella、Giovanni Piancatelli、Antonella Squarcia、Carla Trolli

  DOI：10.1016/s0040-4039(00)00439-1

  日期：2000.5

  Deprotonation of N-benzyl-3-phenylselenylpyrrol-2(5H)-one 3 and furan-2(5H)-one 4 and reaction with aldehydes affords regioselectively 5-(1'-hydroxy)-gamma-butyrolactones and the aza-analogous butyrolactams with good diastereoisomeric excesses. The presence of Lewis acids enhances the diastereoisomeric ratios.This methodology is an alternative to Lewis acid mediated silyloxydiene condensation. (C) 2000 Elsevier Science Ltd. All rights reserved.
• General, Regiodefined Access to α-Substituted Butenolides through Metal−Halogen Exchange of 3-Bromo-2-silyloxyfurans. Efficient Synthesis of an Anti-inflammatory Gorgonian Lipid
  作者：John Boukouvalas、Richard P. Loach

  DOI：10.1021/jo8015924

  日期：2008.10.17

  A variety of alpha-substituted butenolides were efficiently prepared from 3-bromo-2-triisopropylsilyloxyfuran via lithium-bromine exchange and in situ quench with carbon or heteroatom electrophiles. The inherent flexibility of this methodology is illustrated by a short and efficient synthesis of an anti-inflammatory marine natural product.
• 3-Phenylselanylfuran-2(5H)-one: a versatile building block in the synthesis of lignans. A new approach towards 3,4-dibenzyl γ-butyrolactones
  作者：Marco Bella、Giovanni Piancatelli、Maria Cristina Pigro

  DOI：10.1016/s0040-4020(99)00721-8

  日期：1999.10

  Ready available 3-phenylselanylfuran-2(5H)-one undergoes tandem conjugate addition-alkylation by organocopper reagents to afford, with good yields and diastereoselectivities, 3,4-disubstituted-3-phenylselanyl-γ-butyrolactones, which can be transformed into naturally occurring compounds, such as lignans.

  现成的3-苯基硒基呋喃-2（5 H）-一通过有机铜试剂进行串联共轭加成-烷基化，以良好的收率和非对映选择性提供3,4-二取代的-3-苯基硒基-γ-丁内酯，可以将其转化为天然存在的化合物，例如木脂素。