tert-butyl 4-(1,2-dihydroxyethyl)phenylcarbamate | 1247181-60-7

• 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: tert-butyl 4-(1,2-dihydroxyethyl)phenylcarbamate
• 英文别名: tert-butyl N-[4-(1,2-dihydroxyethyl)phenyl]carbamate
• CAS: 1247181-60-7
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: ZIIHZSIIZSNOFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  78.79
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  tert-butyl 4-vinylphenylcarbamate 在 6,7-二氧杂螺[3.4]辛烷-5,8-二酮 、 水 、 sodium hydroxide 作用下， 以 氯仿 为溶剂， 反应 28.0h， 以56%的产率得到tert-butyl 4-(1,2-dihydroxyethyl)phenylcarbamate
  参考文献：
  名称：

  Alkene Syn Dihydroxylation with Malonoyl Peroxides

  摘要：

  Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 degrees C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to > 50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.

  DOI：

  10.1021/ja1066674

文献信息

• Metal-Free Dihydroxylation of Alkenes using Cyclobutane Malonoyl Peroxide
  作者：Kevin M. Jones、Nicholas C. O. Tomkinson

  DOI：10.1021/jo202084w

  日期：2012.1.20

  Cyclobutane malonoyl peroxide (7), prepared in a single step from the commercially available diacid 6, is an effective reagent for the dihydroxylation of alkenes. Reaction of a chloroform solution of 7 with an alkene in the presence of I equiv of water at 40 degrees C followed by alkaline hydrolysis leads to the corresponding diol (30-84%). With 1,2-disubstituted alkenes, the reaction proceeds with syn-selectivity (3:1 -> 50:1). A mechanism consistent with experimental findings is proposed, which is supported by deuterium and oxygen labeling studies and explains the stereoselectivity observed. Alternative reaction pathways that are dependent on the structure of the starting alkene are also described leading to the synthesis of allylic alcohols and gamma-lactones.