7-Hydroxy-2,2,8-trimethyl-3,4-dihydro-2H-<1>benzopyran | 73290-80-9

• 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: 7-Hydroxy-2,2,8-trimethyl-3,4-dihydro-2H-<1>benzopyran
• 英文别名: 3,4-dihydro-7-hydroxy-2,2,8-trimethyl-2H-1-benzopyran；7-hydroxy-2,2,8-trimethyl-3,4-dihydro-2H-1-benzopyran；2,2,8-trimethylchroman-7-ol；2,2,8-Trimethyl-3,4-dihydrochromen-7-ol
• CAS: 73290-80-9
• 化学式: C₁₂H₁₆O₂
• mdl: MFCD00601119
• 分子量: 192.258
• InChiKey: NJZXGYBSNRPLPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-Hydroxy-2,2,8-trimethyl-3,4-dihydro-2H-<1>benzopyran 在 硫酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 102.0h， 生成 8,8,10-trimethyl-2H,8H-benzo<1,2-b;5,4-b'>dipyran-2-one
  参考文献：
  名称：

  Ahluwalia; Bala, Acta Chimica Hungarica, 1983, vol. 113, # 2, p. 143 - 148

  摘要：

  DOI：
• 作为产物：
  描述：

  7-羟基-2,2,8-三甲基-2,3-二氢-4H-苯并吡喃-4-酮 生成 7-Hydroxy-2,2,8-trimethyl-3,4-dihydro-2H-<1>benzopyran
  参考文献：
  名称：

  SHAIKH S.; USAONKAR R. N., INDIAN J. CHEM., 1979, B 18, NO 5, 405-408

  摘要：

  DOI：

文献信息

• An unexpected acid mediated rearrangement of monoethylene ketal of 2-methyl-2-(3-methylbut-2-en-1-yl)cyclohex-4-ene-1,3-diones to chromane
  作者：Kukkamudi Sreenivas、Faiz Ahmed Khan

  DOI：10.1016/j.tetlet.2018.02.045

  日期：2018.3

  We herein report a serendipitously observed acid mediated rearrangement of monoethylene ketal of 2-methyl-2-(3-methylbut-2-en-1-yl)cyclohex-4-ene-1,3-diones to Dihydrobenzopyran and demonstrated the application of this methodology in the construction of core carbon scaffolds of dimethoxyajacareubin, cariphenone-A and crotamadine.

  我们在本文中报道了偶然观察到的酸介导的2-甲基-2-（3-甲基丁-2-烯-1-基）环己-4-烯-1,3-二酮的单亚乙基缩酮对二氢苯并吡喃的重排，并证明了其的应用。该方法可用于构建二甲氧基ajacareubin，cariphenone-A和crotamadine的核心碳支架。
• Ahluwalia, V. K.; Mittal, Bina; Mehta, Vimal D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1148 - 1149
  作者：Ahluwalia, V. K.、Mittal, Bina、Mehta, Vimal D.

  DOI：——

  日期：——
• Ahluwalia; Mann; Bala, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 3, p. 247 - 251
  作者：Ahluwalia、Mann、Bala

  DOI：——

  日期：——
• Pancreatic α-amylase inhibition and free radical scavenging activity of substituted pyranochromenone derivatives
  作者：J. Ashok Kumar、Ashok K. Tiwari、G. Saidachary、Chandan Kishor、D. Anand Kumar、Zehra Ali、B. Sridhar、Anthony Addlagatta、B. China Raju

  DOI：10.1007/s00044-013-0867-y

  日期：2014.6

  Pyranochromenone derivatives 3a-d, 6a-j and 2H-chromenones 8a-b were synthesized and screened for their in vitro alpha-amylase inhibitory and ABTS(aEuro cent+) [2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)] free radical scavenging activities. Compounds 3a, 3c, and 6d displayed dual function of ABTS(aEuro cent+) radical scavenging as well as alpha-amylase inhibition. Compound 6h was found to be most potent alpha-amylase inhibitor in present series of compounds. Docking studies suggest that these compounds occupy active site of the human pancreatic alpha-amylase similar to that of acarbose which inhibits enzyme by hydrophobic interactions. These compounds have potential to be developed as therapeutics targeted against diet-induced hyperglycemia in diabetes.Series of pyranochromenone derivatives 3a-d, 6a-j, and 8a-b were synthesized, among these compound 6h shown potent intestinal alpha-amylase inhibitory activity. Compounds 3a, 3c, and 6d were shown dual properties such as alpha-amylase inhibitory and antioxidant activities. These derivatives may serve as a model compounds for design and development of therapeutics based agents.
• Pathak, S. D.; Mujumdar, A. S.; Usgaonkar, R. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, p. 767 - 768
  作者：Pathak, S. D.、Mujumdar, A. S.、Usgaonkar, R. N.

  DOI：——

  日期：——