4b,7,9b-trihydroxy-4b,9b-dihydro-10H-benzo[b]indeno[2,1-d]furan-10-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4b,7,9b-trihydroxy-4b,9b-dihydro-10H-benzo[b]indeno[2,1-d]furan-10-one
• 英文别名: 4b,7,9b-trihydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one；1,5,9-Trihydroxy-8-oxatetracyclo[7.7.0.0^2,7^.0^10,15^]hexadeca-2,4,6,10(15),11,13-hexaen-16-one；(4bR,9bR)-4b,7,9b-trihydroxyindeno[1,2-b][1]benzofuran-10-one
• 化学式: C₁₅H₁₀O₅
• 分子量: 270.241
• InChiKey: GNTRISFKPAMKDM-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  水合茚三酮 、 间苯二酚 在 silica gel 作用下， 反应 0.03h， 以82%的产率得到4b,7,9b-trihydroxy-4b,9b-dihydro-10H-benzo[b]indeno[2,1-d]furan-10-one
  参考文献：
  名称：

  Kundu, Sandip Kumar; Patra, Amarendra; Pramanik, Animesh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 3, p. 604 - 611

  摘要：

  DOI：

文献信息

• Kundu, Sandip Kumar; Patra, Amarendra; Pramanik, Animesh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 3, p. 604 - 611
  作者：Kundu, Sandip Kumar、Patra, Amarendra、Pramanik, Animesh

  DOI：——

  日期：——
• Identification and evaluation of antioxidant, analgesic/anti-inflammatory activity of the most active ninhydrin–phenol adducts synthesized
  作者：K.R. Prabhakar、V.P. Veerapur、Punit Bansal、K. Parihar Vipan、K.M. Reddy、Atanu Barik、Bharat Kumar D. Reddy、P. Reddanna、K.I. Priyadarsini、M.K. Unnikrishnan

  DOI：10.1016/j.bmc.2006.06.068

  日期：2006.11

  Treatment of phenols with ninhydrin in acidic medium afforded 2-hydroxy-2-(ortho-hydroxy-phenyl/naphthyl)-1,3-dioxoindanes, which being unstable were isolated in their hemiketal forms. These synthesized compounds were subjected to TLC screening for radical scavenging and in vitro lipoxgenase and cycloxygenase enzyme inhibition assays. The best compound was identified and studied in detail for steady-state and time-resolved free radical kinetics, viz., DPPH, ABTS(.-), (OH)-O-. and rate constants for these reactions were evaluated. The best compound was also subjected to in vivo anti-inflammatory and analgesic activities in which the compound showed good promise for further structural optimization. (c) 2006 Elsevier Ltd. All rights reserved.
• A biomimetic synthesis of (−)-ascorbyl phloroglucinol and studies toward the construction of ascorbyl-modified catechin natural products and analogues
  作者：Sneha A. Belapure、Zachary G. Beamer、John E. Bartmess、Shawn R. Campagna

  DOI：10.1016/j.tet.2011.09.102

  日期：2011.12

  A method for appending the ascorbyl moiety onto the framework of phenolic natural products has been developed. This reaction proceeds in two steps from.-ascorbic acid and employs acetic acid catalysis. Excellent stereoselectivity is observed during C C bond formation between the phenolic compound and dehydroascorbic acid, and the process is also chemoselective for phenol derivatives bearing electron-donating substituents in each of the 1, 3, and 5 positions. Further, good regioselectivity was also observed when phenols lacking an axis of C-2 symmetry were employed. This method has led to the synthesis of (-)-ascorbyl phloroglucinol as well as the tetracyclic core of ascorbyl-modified catechin natural products. (C) 2011 Elsevier Ltd. All rights reserved.