5,8-Dimethoxyisochroman | 82301-04-0

• 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: 5,8-Dimethoxyisochroman
• 英文别名: 2,5-dimethoxyisochroman；5,8-dimethoxy-3,4-dihydro-1H-isochromene
• CAS: 82301-04-0
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: HIVGWJAGXAYLBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,8-Dimethoxyisochroman 在 molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 [(2S,3S,4S,6S)-6-[[(1S)-5,8-dimethoxy-3,4-dihydro-1H-isochromen-1-yl]oxy]-2-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] 4-nitrobenzoate
  参考文献：
  名称：

  DDQ-Induced, Anomeric Specific, and Diastereoselective Benzylic Glycosidation: A Novel Approach to Heterocyclic Anthracycline Antibiotics

  摘要：

  A novel and efficient method for the oxidative glycosidation at the heterosubstituted benzylic positions with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) is described. The reaction is stereospecific with 3-substituted isochromans and isothiochroman, as well as diastereoselective with non-3-substituted isochromans. The glycosidation with a mixture of alpha- and beta-anomeric free sugars gives alpha-glycosides with absolute stereochemical control on the anomeric center. The synthetic utility of this novel methodology is demonstrated by a short, efficient, and stereoselective total synthesis of heteroanthracycline antitumor reagents.

  DOI：

  10.1021/jo00096a032
• 作为产物：
  描述：

  propyl 2,5-dimethoxyphenylacetate 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 48.0h， 生成 5,8-Dimethoxyisochroman
  参考文献：
  名称：

  Retamal, J. I.; Ruiz, V. M.; Tapia, R. A., Synthetic Communications, 1982, vol. 12, # 4, p. 279 - 286

  摘要：

  DOI：

文献信息

• DDQ-induced and stereoselective functionalization at heterosubstituted benzylic positions by carbon nucleophiles
  作者：Xu Yao-Chang、Caroline Roy、Elaine Lebeau

  DOI：10.1016/s0040-4039(00)61387-4

  日期：1993.12
• RETAMAL, J. I.;RUIZ, V. M.;TAPIA, R. A.;VALDERRAMA, J. A.;VEGA, J. C., SYNTH. COMMUN., 1982, 12, N 4, 279-285
  作者：RETAMAL, J. I.、RUIZ, V. M.、TAPIA, R. A.、VALDERRAMA, J. A.、VEGA, J. C.

  DOI：——

  日期：——
• DDQ-Induced, Anomeric Specific, and Diastereoselective Benzylic Glycosidation: A Novel Approach to Heterocyclic Anthracycline Antibiotics
  作者：Yao-Chang Xu、Elaine Lebeau、Giorgio Attardo、Peter L. Myers、John W. Gillard

  DOI：10.1021/jo00096a032

  日期：1994.8

  A novel and efficient method for the oxidative glycosidation at the heterosubstituted benzylic positions with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) is described. The reaction is stereospecific with 3-substituted isochromans and isothiochroman, as well as diastereoselective with non-3-substituted isochromans. The glycosidation with a mixture of alpha- and beta-anomeric free sugars gives alpha-glycosides with absolute stereochemical control on the anomeric center. The synthetic utility of this novel methodology is demonstrated by a short, efficient, and stereoselective total synthesis of heteroanthracycline antitumor reagents.
• Retamal, J. I.; Ruiz, V. M.; Tapia, R. A., Synthetic Communications, 1982, vol. 12, # 4, p. 279 - 286
  作者：Retamal, J. I.、Ruiz, V. M.、Tapia, R. A.、Valderrama, J. A.、Vega, J. C.

  DOI：——

  日期：——