3-(hydroxy(phenyl)methyl)furan-2(5H)-one | 66341-20-6

• 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-(hydroxy(phenyl)methyl)furan-2(5H)-one
• 英文别名: 2-(1-hydroxybenzyl)-2-buten-4-olide；3-(hydroxy-phenyl-methyl)-5H-furan-2-one；3-(α-Hydroxybenzyl)-2(5H)-furanon；3-[hydroxy(phenyl)methyl]-2(5H)-furanone；4-[hydroxy(phenyl)methyl]-2H-furan-5-one
• CAS: 66341-20-6
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: DMFYHNYZUXVHQU-UHFFFAOYSA-N

物化性质

• 沸点：
  429.8±33.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(hydroxy-phenyl-methyl)-4-phenylsulfanyl-dihydro-furan-2-one 在 sodium periodate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 72.5h， 生成 3-(hydroxy(phenyl)methyl)furan-2(5H)-one
  参考文献：
  名称：

  Aldol Reaction of Aluminium Enolate Resulting from 1,4-Addition of R₂AlX to α,β-Unsaturated Carbonyl Compound. A 1-Acylethenyl Anion Equivalent

  摘要：

  有机铝试剂R2AlX（X=SPh，SeMe）能够以1,4-的方式容易地加成到α,β-不饱和羰基化合物上。生成的铝烯醇盐与醛反应，以较好至良好的产率得到醛醇加合物。通过形式上的HX消除反应，从加合物中可以得到α-取代的α,β-不饱和羰基化合物。整个转化过程相当于醛对1-酰基乙烯基负离子等价物的加成。二乙基铝碘也被发现是实现这种类型转化的有效试剂。

  DOI：

  10.1246/bcsj.54.274

文献信息

• General switch in regioselectivity in the Mukaiyama aldol reaction of silyloxyfuran with aldehydes in aqueous solvents
  作者：Marta Woyciechowska、Gwenael Forcher、Szymon Buda、Jacek Mlynarski

  DOI：10.1039/c2cc36656h

  日期：——

  An unexpected yet disciplined course of catalytic Mukaiyama-aldol reaction instead of the expected vinylogous Mukaiyama-aldol reaction has been observed for the reaction of silyloxyfuran with various aldehydes under Lewis acid catalytic control in water-containing solvents.

  第 V 组金属化合物与三氧化硫的反应
• Aldol reaction of aluminium enolate resulting from 1,4-addition of Me2AlSPh to α,β-unsaturated carbonyl compound. A 1-acylethenyl anion equivalent
  作者：Akira Itoh、Shuji Ozawa、Koichiro Oshima、Hitosi Nozaki

  DOI：10.1016/s0040-4039(01)85473-3

  日期：1980.1
• Thiourea-catalyzed Morita–Baylis–Hillman reaction
  作者：Yoshihiro Sohtome、Nobuko Takemura、Rika Takagi、Yuichi Hashimoto、Kazuo Nagasawa

  DOI：10.1016/j.tet.2008.07.087

  日期：2008.9

  Here, we describe our studies on the thiourea-catalyzed Morita-Baylis-Hillman (MBH) reaction. Chemoselective activation of carbonyl compounds via hydrogen bonding to thiourea as a catalyst is the key to drastic rate acceleration of this reaction. The application of chiral bis-thiourea-type organocatalysts, which can form a chiral double hydrogen-bonding network, is effective for enantioselective MBH reaction. A cooperative system of bis-thiourea compounds, synthesized from 1,2-diaminocyclohexane, and a Lewis base effectively promotes the MBH reaction at lower temperature, affording the MBH adducts in 33-95% yield with 44-90% ee. A plausible transition state model of the enantioselective MBH reaction is presented. (C) 2008 Elsevier Ltd. All rights reserved.
• Acceleration of the Morita−Baylis−Hillman Reaction by a Simple Mixed Catalyst System
  作者：Alejandro Bugarin、Brian T. Connell

  DOI：10.1021/jo900603w

  日期：2009.6.19

  By using a catalytic amount of 4-dimethylaminopyridine (DMAP) as a nucleophile in the presence of an equal amount of tetramethylethylenediamine (TMEDA) and MgI2, Morita-Baylis-Hillman adducts can be obtained in good to excellent yields from various aromatic and aliphatic aldehydes and cyclic enones/enoates at room temperature after convenient reaction times.
• Aldol Reaction of Aluminium Enolate Resulting from 1,4-Addition of R₂AlX to α,β-Unsaturated Carbonyl Compound. A 1-Acylethenyl Anion Equivalent
  作者：Akira Itoh、Shuji Ozawa、Koichiro Oshima、Hitosi Nozaki

  DOI：10.1246/bcsj.54.274

  日期：1981.1

  Organoaluminium reagents R2AlX (X=SPh, SeMe) easily add to α,β-unsaturated carbonyl compounds in 1,4-fashion. The resulting aluminium enolates react with aldehydes to give aldol adducts in fair to good yields. Formal elimination of HX from the adducts provides α-substituted α,β-unsaturated carbonyl compounds. The overall transformation is an addition of aldehydes to 1-acylethenyl anion equivalent. Diethylaluminium iodide also is found to be an efficient reagent for the same type transformation.

  有机铝试剂R2AlX（X=SPh，SeMe）能够以1,4-的方式容易地加成到α,β-不饱和羰基化合物上。生成的铝烯醇盐与醛反应，以较好至良好的产率得到醛醇加合物。通过形式上的HX消除反应，从加合物中可以得到α-取代的α,β-不饱和羰基化合物。整个转化过程相当于醛对1-酰基乙烯基负离子等价物的加成。二乙基铝碘也被发现是实现这种类型转化的有效试剂。