(2R,3R,10aR)-3,10a-dihydro-2-methoxymethyl-3-methoxy-7-methyl-2H,5H-pyrano[2,3-b][1]benzopyran | 1146980-48-4

• 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: (2R,3R,10aR)-3,10a-dihydro-2-methoxymethyl-3-methoxy-7-methyl-2H,5H-pyrano[2,3-b][1]benzopyran
• 英文别名: (2R,3R,10aR)-3-methoxy-2-(methoxymethyl)-7-methyl-2,3,5,10a-tetrahydropyrano[2,3-b]chromene
• CAS: 1146980-48-4
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: WXLWWLDMXKXEMC-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对甲酚 、 [(2R,3R,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methanol 在 三氟乙酸 作用下， 反应 0.05h， 以94%的产率得到(2R,3R,10aR)-3,10a-dihydro-2-methoxymethyl-3-methoxy-7-methyl-2H,5H-pyrano[2,3-b][1]benzopyran
  参考文献：
  名称：

  Trifluoroacetic acid-mediated facile transformation of 2-C-hydroxymethyl-d-glycals to chiral pyrano[2,3-b]benzopyrans

  摘要：

  Treatment of 2-C-hydroxymetilyi-D-glyCalS With phenols in trifluoroacetic acid at ambient temperature leads to an extremely facile transformation affording chiral pyrano[2,3-b]benzopyrans in high yields. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.12.020

文献信息

• Montmorillonite K-10 clay-catalyzed Ferrier rearrangement of 2-C-hydroxymethyl-d-glycals, 3,4,6-tri-O-alkyl-d-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol: a few unexpected domino transformations
  作者：Elumalai Kumaran、Meenakshisundaram Santhi、Kalpattu K. Balasubramanian、Shanmugasundaram Bhagavathy

  DOI：10.1016/j.carres.2011.03.027

  日期：2011.9

  3-b]benzopyrans. This montmorillonite K-10 clay-catalyzed transformation is facile both under ambient (Method 1) and microwave conditions (Method 2). Ferrier rearrangement of 3,4-(dihydro-2H-pyran-5-yl)methanol with p-cresol, 2,6-xylenol, and ethanol led to totally unexpected transformations. Reaction of 2-C-hydroxymethyl-d-galactal with 2,6-dimethylphenol in the presence of montmorillonite K-10 led to a novel

  蒙脱石K-10粘土催化的3,4,6-三-O-烷基-2-C-羟甲基-d-糖基，3,4,6-三-O-乙酰基-d-糖基，3，描述了4,6-三-O-烷基-d-糖和3,4-（二氢-2H-吡喃-5-基）甲醇与少量醇和酚。2-C-羟甲基-d-缩醛与酚的反应类似于2-C-乙酰氧基甲基-d-缩醛的反应，得到吡喃并[2,3-b]苯并吡喃。这种蒙脱土K-10粘土催化的转化在环境（方法1）和微波条件（方法2）下都很容易。3,4-（二氢-2H-吡喃-5-基）甲醇与对甲酚，2,6-二甲苯酚和乙醇的重排反应导致完全出乎意料的转化。在蒙脱石K-10存在下，2-C-羟甲基-d-半乳糖与2,6-二甲基苯酚的反应导致了新的多米诺骨牌转化，提供了4-（5'，6' -二氢-4H-吡喃-3′-基甲基）-2，6-二甲基苯酚。相比之下，3,4,6-三-O-乙酰基-d-葡糖醇提供了Ferrier重排产物，即2,6-二甲基苯基4,6-二-O-乙酰基-2
• Tailor-made chiral pyranopyrans based on glucose and galactose and studies on self-assembly of some crystals and low molecular weight organogel (LMOG)
  作者：Soumik Roy、Arijit Chakraborty、Basab Chattopadhyay、Abir Bhattacharya、Alok K. Mukherjee、Rina Ghosh

  DOI：10.1016/j.tet.2010.08.054

  日期：2010.10

  InCl3 catalyzed reactions of 2-C-acetoxymethylglycal derivatives with different phenolic compounds resulted in the formation of sugar based pyranoarenopyrans in good yields and moderate to excellent diastereoselectivity in favor of 10aR- or 12aR- or 14aR-products. One of the synthesized compounds, viz. (2R,3R,12aR)-2,3,5,12a-tetrahydro-2-methoxymethyl-3-methoxypyrano[2,3-b]naphtho[1,2-e]pyran gelated polar solvents like MeOH, EtOH and non-polar solvents like pentane, hexane, heptane, octane, pet. ether, etc. The SEM picture of the corresponding hexane xerogel exhibited a rare type of microtubular gel assembly, whereas the SEM pictures of MeOH and pet. ether xerogels showed different types of three-dimensional network. Study of the MeOH gel by Fluorescence spectroscopy, H-1 NMR and X-ray powder diffraction analysis indicated that the supramolecular assembly in the MeOH gel can be attributed to pi-stacking. The crystal packing of (2R.3R,10aR)-3,10a-dihydro-2-methoxymethyl-3-methoxy-7-methyl-2H,5H-pyrano[2,3-b][1]benzopyran, a benzopyran analogue of the above organogelator was stabilized by C-H center dot center dot center dot O and C-H center dot center dot center dot pi hydrogen bonds forming one-dimensional columns parallel to the [001] direction, whereas the corresponding benzopyran 3-epimer showed only C-H center dot center dot center dot O hydrogen bonds among the molecules. (C) 2010 Elsevier Ltd. All rights reserved.
• Trifluoroacetic acid-mediated facile transformation of 2-C-hydroxymethyl-d-glycals to chiral pyrano[2,3-b]benzopyrans
  作者：Meenakshisundaram Santhi、Kalpattu K Balasubramanian、Shanmugasundaram Bhagavathy

  DOI：10.1016/j.carres.2008.12.020

  日期：2009.3

  Treatment of 2-C-hydroxymetilyi-D-glyCalS With phenols in trifluoroacetic acid at ambient temperature leads to an extremely facile transformation affording chiral pyrano[2,3-b]benzopyrans in high yields. (C) 2008 Elsevier Ltd. All rights reserved.