6-acetyl-7-acetoxy-2,2-dimethyl-3-chromene | 19013-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-acetyl-7-acetoxy-2,2-dimethyl-3-chromene
• 英文别名: 1-(7-acetoxy-2,2-dimethyl-2H-chromen-6-yl)-ethanone；7-Acetoxy-2,2-dimethyl-6-acetyl-chromen；(6-Acetyl-2,2-dimethylchromen-7-yl) acetate
• CAS: 19013-04-8
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: MBIPWSNIWPBTGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-acetyl-7-acetoxy-2,2-dimethyl-3-chromene 在 R,R-Jacobsen's catalyst 、 N-甲基吗啉氧化物 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到6-acetyl-3,4-epoxy-7-acetoxy-2,2-dimethyl-chroman
  参考文献：
  名称：

  The first asymmetric total synthesis of several 3,4-dihydroxy-2,2-dimethyl-chroman derivatives

  摘要：

  The stereoisomers of 3,4-dihydroxy-6-methoxy-2,2-dimethyl-chroman 1a-c and 3,4,7-trihydroxy-6-acetyl-2,2-dimethyl-chroman 2a-c were conveniently prepared for the first time via a synthesis in which Sharpless asymmetric dihydroxylation and Jacobsen's catalytic asymmetric epoxidation are the key steps. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.040
• 作为产物：
  描述：

  1-(7-hydroxy-2,2-dimethylchroman-6-yl)ethanone 在 吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 6-acetyl-7-acetoxy-2,2-dimethyl-3-chromene
  参考文献：
  名称：

  The first asymmetric total synthesis of several 3,4-dihydroxy-2,2-dimethyl-chroman derivatives

  摘要：

  The stereoisomers of 3,4-dihydroxy-6-methoxy-2,2-dimethyl-chroman 1a-c and 3,4,7-trihydroxy-6-acetyl-2,2-dimethyl-chroman 2a-c were conveniently prepared for the first time via a synthesis in which Sharpless asymmetric dihydroxylation and Jacobsen's catalytic asymmetric epoxidation are the key steps. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.10.040

文献信息

• Chromans from helianthella quinquenervis
  作者：Werner Herz、Palaniappan Kulanthaivel

  DOI：10.1016/s0031-9422(00)80347-7

  日期：1984.1
• The first asymmetric total synthesis of several 3,4-dihydroxy-2,2-dimethyl-chroman derivatives
  作者：Qiaoling Wang、Xuegong She、Xinfeng Ren、Junying Ma、Xinfu Pan

  DOI：10.1016/j.tetasy.2003.10.040

  日期：2004.1

  The stereoisomers of 3,4-dihydroxy-6-methoxy-2,2-dimethyl-chroman 1a-c and 3,4,7-trihydroxy-6-acetyl-2,2-dimethyl-chroman 2a-c were conveniently prepared for the first time via a synthesis in which Sharpless asymmetric dihydroxylation and Jacobsen's catalytic asymmetric epoxidation are the key steps. (C) 2003 Elsevier Ltd. All rights reserved.