(3S,4S)-3,4-dihydroxy-6-methoxy-2,2-dimethyl-chroman | 31298-60-9

• 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: (3S,4S)-3,4-dihydroxy-6-methoxy-2,2-dimethyl-chroman
• 英文别名: cis-3,4-Dihydroxy-6-methoxy-2,2-dimethyl-chroman；(3S,4S)-6-methoxy-2,2-dimethyl-3,4-dihydrochromene-3,4-diol
• CAS: 31298-60-9
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: WYTBEDBPRKCHGY-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3,4-dihydroxy-6-methoxy-2,2-dimethyl-chroman 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 5.0h， 以79%的产率得到(3R)-3-hydroxy-6-methoxy-2,2-dimethyl-3H-chromen-4-one
  参考文献：
  名称：

  Selective oxidation of benzylic or allylic hydroxyl group of sec-1,2-diols

  摘要：

  A mild and efficient method to selectively oxidize chiral sec-1,2-diols has been developed, which demonstrates that 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) can selectively oxidize benzylic or allylic hydroxyl group of sec-1,2-diols under ultrasound wave promotion. The configuration of the adjacent chiral center is retained. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.073
• 作为产物：
  描述：

  6-羟基-2,2-二甲基色满 在 sodium tetrahydroborate 、 甲基磺酰胺 、 AD-mix-β 、 potassium carbonate 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 58.5h， 生成 (3S,4S)-3,4-dihydroxy-6-methoxy-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

文献信息

• Selective oxidation of benzylic or allylic hydroxyl group of sec-1,2-diols
  作者：Kun Peng、Fuxin Chen、Xuegong She、Chunhui Yang、Yuxin Cui、Xinfu Pan

  DOI：10.1016/j.tetlet.2004.12.073

  日期：2005.2

  A mild and efficient method to selectively oxidize chiral sec-1,2-diols has been developed, which demonstrates that 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) can selectively oxidize benzylic or allylic hydroxyl group of sec-1,2-diols under ultrasound wave promotion. The configuration of the adjacent chiral center is retained. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.