4b,7,9,9b-tetrahydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-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,7,9,9b-tetrahydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one
• 英文别名: (4bR,9bR)-4b,7,9,9b-tetrahydroxyindeno[1,2-b][1]benzofuran-10-one
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: YXUNOMLOJLVBIJ-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 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：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯并[f]茚三酮 、 4b,7,9,9b-tetrahydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one 在 溶剂黄146 作用下， 反应 72.0h， 以91%的产率得到
  参考文献：
  名称：

  间苯三酚和vic多羰基化合物之间的反应：双极面碗形化合物Kim合成的扩展和机理研究

  摘要：

  金并通过间苯三酚和茚三酮之间的一锅反应意外地合成了新的cavitand。通过用苯并[ n ]茚三酮代替茚三酮可得到更深的空洞。同时使用茚三酮和苯并[ f ]茚三酮进行反应，可提供较低对称性的“混合碗”。其他环状聚酮，例如1，2-茚满二酮和四氧嘧啶与间苯三酚仅形成部分封闭的结构。该反应中中间体化合物的晶体学研究证实了金的假设，即碗的形成涉及半缩环的开环和重排。

  DOI：

  10.1016/j.tet.2009.07.056
• 作为产物：
  描述：

  间苯三酚 、 1,2,3-茚满三酮 以 溶剂黄146 为溶剂， 反应 3.0h， 以78%的产率得到4b,7,9,9b-tetrahydroxy-4bH-indeno[1,2-b]benzofuran-10(9bH)-one
  参考文献：
  名称：

  Serendipitous one-pot synthesis of brand-new, bowl-shaped molecular architecture from phloroglucinol and ninhydrin

  摘要：

  We prepared a brand-new, bowl-shaped molecular architecture in one step from the reaction of ninhydrin and phloroglucinol in acetic acid in excellent yield (95%) in a one-pot reaction and the bipolarofacial nature of this compound was confirmed by its X-ray structure. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.117

文献信息

• 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.
• 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：——
• The reaction between phloroglucinol and vic polycarbonyl compounds: extension and mechanistic elucidation of Kim's synthesis for bipolarofacial bowl-shaped compounds
  作者：Joseph Almog、Rinat Rozin、Asne Klein、Genyia Shamuilov-Levinton、Shmuel Cohen

  DOI：10.1016/j.tet.2009.07.056

  日期：2009.9

  serendipitous synthesis of a novel cavitand by the one-pot reaction between phloroglucinol and ninhydrin was revisited and extended. A much deeper cavitand was obtained by replacing ninhydrin with benzo[f]ninhydrin. Performing the reaction in a stepwise manner, employing both ninhydrin and benzo[f]ninhydrin, provided ‘mixed bowls’ of lower symmetry. Other cyclic polyketones, such as 1,2-indanedione and alloxan

  金并通过间苯三酚和茚三酮之间的一锅反应意外地合成了新的cavitand。通过用苯并[ n ]茚三酮代替茚三酮可得到更深的空洞。同时使用茚三酮和苯并[ f ]茚三酮进行反应，可提供较低对称性的“混合碗”。其他环状聚酮，例如1，2-茚满二酮和四氧嘧啶与间苯三酚仅形成部分封闭的结构。该反应中中间体化合物的晶体学研究证实了金的假设，即碗的形成涉及半缩环的开环和重排。
• Serendipitous one-pot synthesis of brand-new, bowl-shaped molecular architecture from phloroglucinol and ninhydrin
  作者：Jeong Eun Na、Ka Young Lee、Joobeom Seo、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2005.04.117

  日期：2005.6

  We prepared a brand-new, bowl-shaped molecular architecture in one step from the reaction of ninhydrin and phloroglucinol in acetic acid in excellent yield (95%) in a one-pot reaction and the bipolarofacial nature of this compound was confirmed by its X-ray structure. (c) 2005 Elsevier Ltd. All rights reserved.