(2R,3R,14aR)-2,3,5,14a-tetrahydro-2-methoxymethyl-3-methoxypyrano[2,3-b]phenanthreno[9,10-e]pyran | 1256636-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (2R,3R,14aR)-2,3,5,14a-tetrahydro-2-methoxymethyl-3-methoxypyrano[2,3-b]phenanthreno[9,10-e]pyran
• 英文别名: (16R,18R,19R)-19-methoxy-18-(methoxymethyl)-15,17-dioxapentacyclo[12.8.0.02,7.08,13.016,21]docosa-1(14),2,4,6,8,10,12,20-octaene
• CAS: 1256636-29-9
• 化学式: C₂₃H₂₂O₄
• 分子量: 362.425
• InChiKey: PJQQJENLCHBYBD-MQSCRBSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  9-羟基菲 、 [(2R,3R,4R)-3,4-dimethoxy-2-(methoxymethyl)-3,4-dihydro-2H-pyran-5-yl]methyl acetate 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以81%的产率得到(2R,3R,14aR)-2,3,5,14a-tetrahydro-2-methoxymethyl-3-methoxypyrano[2,3-b]phenanthreno[9,10-e]pyran
  参考文献：
  名称：

  Tailor-made chiral pyranopyrans based on glucose and galactose and studies on self-assembly of some crystals and low molecular weight organogel (LMOG)

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.08.054

文献信息

• 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.