(4-hydroxymethyl-2,5-diphenyl-furan-3-yl)-methanol | 4676-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: (4-hydroxymethyl-2,5-diphenyl-furan-3-yl)-methanol
• 英文别名: 3,4-bis(hydroxymethyl)-2,5-diphenylfurane；3,4-bis-hydroxymethyl-2,5-diphenyl-furan；2,5-Diphenyl-2,4-dihydroxymethyl-furan；3,4-Furandimethanol, 2,5-diphenyl-；[4-(hydroxymethyl)-2,5-diphenylfuran-3-yl]methanol
• CAS: 4676-54-4
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: QIFPBDIPSNAMDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-hydroxymethyl-2,5-diphenyl-furan-3-yl)-methanol 在 bis(pyridine)silver(I) permanganate 作用下， 以 苯 为溶剂， 反应 1.0h， 以90%的产率得到diphenyl-2,5 furannedicarbaldehyde 3,4
  参考文献：
  名称：

  高锰酸双吡啶银[Ag（C 5 H 5 N）2 ] MnO 4：有机底物的有效氧化剂

  摘要：

  高锰酸双吡啶银是一种易于制备的晶体，相对稳定的化合物，可溶于有机溶剂。描述了其作为苯中有机化合物的氧化剂的用途。

  DOI：

  10.1016/s0040-4039(00)86758-1
• 作为产物：
  描述：

  diphenyl-2,5 furannedicarbaldehyde 3,4 在 sodium tetrahydroborate 、 sodium hydrogen sulfate 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以97%的产率得到(4-hydroxymethyl-2,5-diphenyl-furan-3-yl)-methanol
  参考文献：
  名称：

  NaBH₄/NaHSO₄·H₂O a Heterogeneous Acidic System for a Mild and Convenient Reduction of Carbonyl Compounds under Protic Condition

  摘要：

  NaBH₄在存在硫酸氢钠（NaHSO₄·H₂O）的情况下，作为一种弱酸试剂，能够高效地将各种羰基化合物如醛、酮、α,β-不饱和醛和酮、α-二酮和酰基酮在乙腈中在非均相条件下还原为它们相应的醇。还原反应可在室温或回流条件下完成。

  DOI：

  10.1515/znb-2005-0417

文献信息

• Reduction of Carbonyl Compounds with NaBH₄ under Ultrasound Irradiation and Aprotic Condition
  作者：Behzad Zeynizadeh、Saiedeh Yahyaei

  DOI：10.1515/znb-2004-0612

  日期：2004.6.1

  A variety of carbonyl compounds are reduced to their corresponding alcohols with sodium borohydride under ultrasound irradiation and aprotic condition. Reduction reactions are performed in THF at room temperature or under reflux condition. The product alcohols were obtained in good to excellent yields. The chemoselective reduction of aldehydes over ketones was achieved successfully with this system.

  一种多种羰基化合物在超声辐射和无极性条件下通过硼氢化钠还原为相应的醇类化合物。还原反应在室温下或回流条件下在THF中进行。产物醇类化合物以良好至优异的产率获得。该体系成功实现了醛类化合物优先还原而不影响酮类化合物的选择性还原。
• Wet THF as a Suitable Solvent for a Mild and Convenient Reduction of Carbonyl Compounds with NaBH₄
  作者：Behzad Zeynizadeh、Tarifeh Behyar

  DOI：10.1246/bcsj.78.307

  日期：2005.2

  NaBH 4 in wet THF can readily reduce varieties of carbonyl compounds such as aldehydes, ketones, conjugated enones, acyloins, and α-diketones to their corresponding alcohols in good to excellent yields. Reduction reactions were performed at room temperature or under reflux condition. In addition, the chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing

  湿 THF 中的 NaBH 4 可以很容易地将各种羰基化合物还原为相应的醇，例如醛、酮、共轭烯酮、酰基和 α-二酮，收率非常好。还原反应在室温或回流条件下进行。此外，使用该还原系统成功地完成了醛相对于酮的化学选择性还原。
• Modified Hydroborate Agent: (2,2′-Bipyridyl)(tetrahydroborato)zinc Complex, [Zn(BH₄)₂(bpy)], as a New, Stable, Efficient Ligand-Metal Hydroborate and Chemoselective Reducing Agent
  作者：Behzad Zeynizadeh

  DOI：10.1246/bcsj.76.317

  日期：2003.2

  rato)zinc complex, [Zn(BH4)2(bpy)], is a new white stable compound which has been used for efficient reduction of variety of carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α,β-unsaturated carbonyl compounds (1,2-reduction) to their corresponding alcohols in acetonitrile at room temperature. Excellent chemoselectivity was also observed for the reduction of aldehydes over ketones

  (2,2'-联吡啶基)(四氢硼酸根)锌配合物，[Zn(BH4)2(bpy)]，是一种新型白色稳定化合物，已用于有效还原各种羰基化合物，如醛、酮、酰基化合物, α-二酮和 α,β-不饱和羰基化合物（1,2-还原）在乙腈中在室温下转化为相应的醇。还观察到使用这种还原剂还原醛而不是酮具有优异的化学选择性。
• Barium Ferrate Monohydrate BaFeO₄·H₂O, a Useful Oxidant for the Oxidation of Organic Compounds under Aprotic Conditions
  作者：Habib Firouzabadi、Daryoush Mohajer、Mohsen Entezari-Moghadam

  DOI：10.1246/bcsj.61.2185

  日期：1988.6

  be used as a versatile reagent in organic synthesis. Primary and secondary alcohols are converted to their carbonyl compounds, α-hydroxy ketones to their diketones, and hydroquinones to their quinones. Aromatic amines are converted to their azo compounds, benzylamine to benzaldehyde, phenylhydrazones and oximes to their carbonyl compounds. Thiols are also converted to their disulfides in high yields

  描述了稍加修饰的高铁酸钡一水合物的制备。结果表明，该试剂能够氧化不同的有机化合物，可用作有机合成中的通用试剂。伯醇和仲醇转化为羰基化合物，α-羟基酮转化为二酮，氢醌转化为醌。芳香胺转化为其偶氮化合物，苄胺转化为苯甲醛，苯腙和肟转化为其羰基化合物。硫醇也以高产率转化为其二硫化物。这种试剂似乎是一种无毒无污染的化合物。
• Bis(2,2'-bipyridyl)copper(II) permanganate (BBCP): A mild and versatile oxidant in organic synthesis
  作者：H. Firouzabadi、A.R. Sardarian、M. Naderi、B. Vessal

  DOI：10.1016/s0040-4020(01)91340-7

  日期：1984.1

  The preparation of bis(2,2'-bipyridyl)copper(II) permanganate (BBCP) is described. The reagent converts alcohols to the corresponding carbonyl compounds, α-hydroxy ketones to diketones, hydroquinone to p-benzoquinone, and compounds with benzylic double bonds to benzaldehyde in high yield. Benzophenone oxime, acetophenone oxime and various benzaldoximes are converted to the corresponding carbonyl compounds

  描述了高锰酸双（2,2'-联吡啶基）铜（II）（BBCP）的制备。该试剂以高收率将醇转化为相应的羰基化合物，将α-羟基酮转化为二酮，将氢醌转化为对苯醌，将具有苄基双键的化合物转化为苯甲醛。通常在温和的条件下，通常以高收率将苯甲酮肟，苯乙酮肟和各种苯甲醛肟转化为相应的羰基化合物，将芳族胺转化为偶氮化合物，将苄胺转化为苯甲醛。