acetic acid 5-methyl-5-phenyl-tetrahydro-furan-3-yl ester | 1015249-51-0

• 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: acetic acid 5-methyl-5-phenyl-tetrahydro-furan-3-yl ester
• 英文别名: 5-methyl-5-phenyltetrahydrofuran-3-yl acetate
• CAS: 1015249-51-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: QNPYAEJIXJTUBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-苯基-4-五亚乙基六胺-2-醇 、 溶剂黄146 在 [Pd(dppp)(H₂O)2]⁽²⁺⁾*2(OTf)^(1-) 碘苯二乙酸 作用下， 反应 40.0h， 以90%的产率得到acetic acid 5-methyl-5-phenyl-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Palladium-Catalyzed Olefin Dioxygenation

  摘要：

  A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and Phl(OAC)(2) as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An (18)O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates.

  DOI：

  10.1021/ja711029u

文献信息

• Copper-Catalyzed Diacetoxylation of Olefins using PhI(OAc)₂ as Oxidant
  作者：Jayasree Seayad、Abdul Majeed Seayad、Christina L. L. Chai

  DOI：10.1021/ol902813m

  日期：2010.4.2

  Copper(I) or -(II) salts with weakly coordinating anions catalyze the diacetoxylation of olefins efficiently in the presence of PhI(OAc)(2) as the oxidant under mild conditions, The reaction is effective for aryl, aryl alkyl, as well as aliphatic terminal and internal olefins forming the corresponding vicinal diacetoxy compounds in 70-85% yields and dr (syn/anti) of up to 5.2. Under these conditions, homoallylic alcohols formed the corresponding tetrahydrofuran derivatives in high yields.