5-(3-oxo-1-phenylbutyl)furan-2(5H)-one | 1241388-92-0

• 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: 5-(3-oxo-1-phenylbutyl)furan-2(5H)-one
• 英文别名: (2S)-2-[(1S)-3-oxo-1-phenylbutyl]-2H-furan-5-one
• CAS: 1241388-92-0
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: PMIJGIQGIICYQE-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲硅氧基-2-呋喃 、 苄叉丙酮 在 碘 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 5-(3-oxo-1-phenylbutyl)furan-2(5H)-one 、 5-(3-oxo-1-phenylbutyl)furan-2(5H)-one
  参考文献：
  名称：

  Iodine-catalyzed 1,4-addition of 2-(trimethylsilyloxy)furan to α,β-unsaturated ketones: a facile synthesis of γ-butenolides

  摘要：

  The alpha,beta-unsaturated compounds undergo smooth conjugate addition with 2-(trimethylsilyloxy)furan (TMSF) in the presence of 10 mol % of iodine under mild and neutral conditions to afford the corresponding gamma-substituted butenolides in high yields and with good diastereoselectivity. The use of iodine makes this procedure simple, convenient and cost effective. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.02.128

文献信息

• Support Effect on Stereoselectivities of Vinylogous Mukaiyama–Michael Reactions Catalyzed by Immobilized Chiral Copper Complexes
  作者：José M. Fraile、Nuria García、Clara I. Herrerías

  DOI：10.1021/cs400743n

  日期：2013.12.6

  Chiral bis(oxazoline)- and azabis(oxazoline)-copper complexes, used as homogeneous catalysts or immobilized onto laponite, are able to catalyze vinylogous Mukaiyama–Michael reactions between 2-(trimethylsilyloxy)furan and several electron-deficient alkenes. A study of the support effect has been conducted and different changes on the diastereoselectivities and enantioselectivities has been observed

  手性双（恶唑啉）和氮杂双（恶唑啉）-铜配合物，用作均相催化剂或固定在锂皂石上，能够催化2-（三甲基甲硅烷氧基）呋喃与几种电子不足的烯烃之间的乙烯基Mukaiyama-Michael反应。已经进行了支持作用的研究，并且观察到非对映选择性和对映选择性的不同变化。取决于底物（迈克尔受体）的结构，催化剂的行为是不同的。当使用亚苄基丙二酸二乙酯时，主要的非对映异构体是具有顺式构型的异构体，但均相和非均相催化剂会导致相反的对映异构体（溶液中-80％ee，异相中38％ee）。这种变化表示约1.8 kcal / mol的支持作用。和N-（E）-but-2-enoyloxazolidinone，最相关的变化是非对映异构体的喜好。在溶液中，反异构体是主要异构体（anti / syn = 98/2）；反异构体是主要异构体。然而，相反，固定的催化剂优选顺式异构体（anti / syn = 19/81）。先前在文献
• Asymmetric vinylogous Michael reaction of α,β-unsaturated ketones with γ-butenolide under multifunctional catalysis
  作者：Huicai Huang、Feng Yu、Zhichao Jin、Wenjun Li、Wenbin Wu、Xinmiao Liang、Jinxing Ye

  DOI：10.1039/c0cc01054e

  日期：——

  general and direct organocatalytic asymmetric vinylogous Michael reaction of gamma-butenolide with alpha,beta-unsaturated ketones was investigated with a multifunctional primary amine salt as catalyst. The reaction enables straightforward access toward synthetically versatile gamma-substituted butenolides from simple 2(5H)-furanone with satisfactory yields, diastereo- and enantioselectivities (up to 30:1

  以多功能伯胺盐为催化剂，研究了γ-丁烯内酯与α，β-不饱和酮的一般直接有机催化不对称乙烯基迈克尔反应。该反应能够从简单的2（5H）-呋喃酮中直接获得合成用途广泛的γ-取代的丁烯内酯，并具有令人满意的产率，非对映体和对映体选择性（高达30：1 dr和95-99％ee）。
• Iodine-catalyzed 1,4-addition of 2-(trimethylsilyloxy)furan to α,β-unsaturated ketones: a facile synthesis of γ-butenolides
  作者：J.S. Yadav、B.V. Subba Reddy、G. Narasimhulu、N. Sivasankar Reddy、P. Janardhan Reddy

  DOI：10.1016/j.tetlet.2009.02.128

  日期：2009.7

  The alpha,beta-unsaturated compounds undergo smooth conjugate addition with 2-(trimethylsilyloxy)furan (TMSF) in the presence of 10 mol % of iodine under mild and neutral conditions to afford the corresponding gamma-substituted butenolides in high yields and with good diastereoselectivity. The use of iodine makes this procedure simple, convenient and cost effective. (C) 2009 Published by Elsevier Ltd.