[(5-Oxooxolan-2-yl)-phenylmethyl] acetate

• 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: [(5-Oxooxolan-2-yl)-phenylmethyl] acetate
• 英文别名: [(5-oxooxolan-2-yl)-phenylmethyl] acetate
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: QXXOVOPMUVHWIN-UHFFFAOYSA-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：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-dichloro-5-(hydroxy(phenyl)methyl)furan-2(5H)-one 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.17h， 生成 [(5-Oxooxolan-2-yl)-phenylmethyl] acetate
  参考文献：
  名称：

  Novel Synthons from Mucochloric Acid:  The First Use of α,β-Dichloro-γ-butenolides and γ-Butyrolactams for Direct Vinylogous Aldol Addition

  摘要：

  Novel 5-(1'-hydroxy)-gamma-butyrolactone and gamma-butyrolactam subunits were synthesized by direct vinylogous aldol addition of alpha,beta-dichloro gamma-butyrolactones and gamma-butyrolactams with aldehydes under basic conditions. Different bases and solvents were screened in the context of generating gamma-butyrolactones. Diastereoselectivity was observed and gamma-butenolides and gamma-butyrolactams showed opposite diastereoselectivity under the same reaction condition.

  DOI：

  10.1021/jo062613l

文献信息

• Palladium-Catalyzed Olefin Dioxygenation
  作者：Yang Li、Datong Song、Vy M. Dong

  DOI：10.1021/ja711029u

  日期：2008.3.1

  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.
• Novel Synthons from Mucochloric Acid:  The First Use of α,β-Dichloro-γ-butenolides and γ-Butyrolactams for Direct Vinylogous Aldol Addition
  作者：Koushik Das Sarma、Ji Zhang、Timothy T. Curran

  DOI：10.1021/jo062613l

  日期：2007.4.1

  Novel 5-(1'-hydroxy)-gamma-butyrolactone and gamma-butyrolactam subunits were synthesized by direct vinylogous aldol addition of alpha,beta-dichloro gamma-butyrolactones and gamma-butyrolactams with aldehydes under basic conditions. Different bases and solvents were screened in the context of generating gamma-butyrolactones. Diastereoselectivity was observed and gamma-butenolides and gamma-butyrolactams showed opposite diastereoselectivity under the same reaction condition.