5-isopropyl-3-methyl-1,6,7-naphthalenetriol | 1256723-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-isopropyl-3-methyl-1,6,7-naphthalenetriol
• 英文别名: 1,6,7-Trihydroxy-5-isopropyl-3-methylnaphthalene；3-methyl-5-propan-2-ylnaphthalene-1,6,7-triol
• CAS: 1256723-06-4
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: FKSSNNFIWCKITC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-二氯甲醚 、 5-isopropyl-3-methyl-1,6,7-naphthalenetriol 在 四氯化钛 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 21.25h， 以16%的产率得到半棉酚
  参考文献：
  名称：

  Synthesis of hemigossypol and its derivatives

  摘要：

  Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-furgal activity compared to gossypol (1), the disesquiterpene chiller of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.089
• 作为产物：
  描述：

  dihydro-5-(2-isopropyl-3,4-dimethoxyphenyl)-4-methyl-2-furanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 以90%的产率得到5-isopropyl-3-methyl-1,6,7-naphthalenetriol
  参考文献：
  名称：

  Synthesis of hemigossypol and its derivatives

  摘要：

  Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-furgal activity compared to gossypol (1), the disesquiterpene chiller of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.089

文献信息

• Synthesis of hemigossypol and its derivatives
  作者：Jun Wei、David L. Vander Jagt、Robert E. Royer、Lorraine M. Deck

  DOI：10.1016/j.tetlet.2010.08.089

  日期：2010.11

  Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-furgal activity compared to gossypol (1), the disesquiterpene chiller of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and its derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives. (C) 2010 Elsevier Ltd. All rights reserved.