2-(2-Phenylpropyl-2)-furan | 15057-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-Phenylpropyl-2)-furan
• 英文别名: 2-(1-methyl-1-phenylethyl)furan；2-(2-Phenylpropan-2-yl)furan
• CAS: 15057-16-6
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: VKSCGTGPHRLMER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-Phenylpropyl-2)-furan 、 乙醛酸正丁酯 在 titanium(IV) isopropylate 、 (R)-6,6'-dibromo-1,1'-binaphth-2-ol 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以95%的产率得到(R)-[5-(1-methyl-1phenyl-ethyl)furan-2-yl]hydroxyacetic acid butyl ester
  参考文献：
  名称：

  Highly Enantioselective Synthesis of 2-Furanyl-hydroxyacetates from Furans via the Friedel−Crafts Reaction

  摘要：

  The Friedel-Crafts reaction of alkyl glyoxylates with variously substituted furans was found to be efficiently catalyzed under simple, undemanding conditions by a 6,6'-dibromo-BINOL/Ti(IV) complex with high enantioselectivity. The reaction afforded chiral substituted 2-furanyl-hydroxyacetic acid esters, compounds of high synthetic interest, in good yield and enantiomeric excess, in most examples in the range of 90-97%.

  DOI：

  10.1021/ol800927w
• 作为产物：
  描述：

  呋喃 、 2-苯基-1-丙烯 在 硫酸 作用下， 以 乙醚 为溶剂， 以60%的产率得到2-(2-Phenylpropyl-2)-furan
  参考文献：
  名称：

  Highly Enantioselective Synthesis of 2-Furanyl-hydroxyacetates from Furans via the Friedel−Crafts Reaction

  摘要：

  The Friedel-Crafts reaction of alkyl glyoxylates with variously substituted furans was found to be efficiently catalyzed under simple, undemanding conditions by a 6,6'-dibromo-BINOL/Ti(IV) complex with high enantioselectivity. The reaction afforded chiral substituted 2-furanyl-hydroxyacetic acid esters, compounds of high synthetic interest, in good yield and enantiomeric excess, in most examples in the range of 90-97%.

  DOI：

  10.1021/ol800927w

文献信息

• Phenyl-furan compounds as vitamin d receptor modulators
  申请人：Gajewski Peter Robert

  公开号：US20070105951A1

  公开（公告）日：2007-05-10

  The present invention relates to novel, non-secosteroidal, phenyl-furan compounds with vitamin D receptor (VDR) modulating activity that are less hypercalcemic than 1α,25dihydroxy vitamin D3. These compounds are useful for treating bone disease and psoriasis.

  本发明涉及一种新型的非次生类固醇苯基呋喃化合物，具有维生素D受体（VDR）调节活性，其低于1α，25-二羟基维生素D3的高钙血症作用。这些化合物可用于治疗骨病和牛皮癣。
• Iron-mediated modular decarboxylative cross-nucleophile coupling
  作者：Grace A. Lutovsky、Samuel N. Gockel、Mark W. Bundesmann、Scott W. Bagley、Tehshik P. Yoon

  DOI：10.1016/j.chempr.2023.04.008

  日期：2023.6

  commercial availability, and structural diversity. Decarboxylative coupling reactions enable versatile functionalization of these feedstock chemicals, but many of the most general methods require prefunctionalization of carboxylic acids with redox-active moieties. These internal oxidants can be costly, their installation impedes rapid library synthesis, and their use results in environmentally problematic

  羧酸因其化学稳定性、商业可用性和结构多样性而成为药物发现的重要组成部分。脱羧偶联反应可以实现这些原料化学品的多功能官能化，但许多最通用的方法需要用氧化还原活性部分对羧酸进行预官能化。这些内氧化剂可能成本高昂，它们的安装阻碍了文库的快速合成，并且它们的使用会产生对环境有问题的有机副产物。我们在此报道了一种由廉价、陆地丰富且无毒的 Fe(III) 盐介导的天然羧酸与亲核偶联配偶体直接脱羧交叉偶联的方法。该方法涉及初始光化学脱羧，然后进行自由基-极性交叉，从而能够构建具有显着通用性的多种碳-碳、碳-氧和碳-氮键。
• Highly Diastereoselective Friedel−Crafts Reaction of Furans with 8-Phenylmenthyl Glyoxylate
  作者：Piotr Kwiatkowski、Jakub Majer、Wojciech Chaładaj、Janusz Jurczak

  DOI：10.1021/ol061943p

  日期：2006.10.1

  The Friedel-Crafts reaction of (1R)-8-phenylmenthyl glyoxylate with variously substituted furans was found to be efficiently promoted by SnCl(4) or magnesium salts with high diastereoselectivities. MgBr(2) performs especially well under simple, undemanding conditions, giving both high yields and high diastereoselectivities (> 90%). The reaction afforded chiral substituted furan-2-yl-hydroxyacetic acid esters, compounds of potentially high synthetic interest.
• Isomerization of 1-trimethylsilylallenyl ether to 1-trimethylsilylpropargyl ether. Preparation of 1-methoxy-1-alken-3-ynes and 2-methoxy-2,5-dihydrofurans
  作者：Isao Kuwajima、Shuichi Sugahara、Jun Enda

  DOI：10.1016/s0040-4039(00)81604-4

  日期：1983.1
• US7468449B2
  申请人：——

  公开号：US7468449B2

  公开（公告）日：2008-12-23