(15R)-10-hydroxy-13-methyl-10,11-dihydro-9H-9,10-[3,4]epipyrroloanthracene-12,14(13H,15H)-dione

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (15R)-10-hydroxy-13-methyl-10,11-dihydro-9H-9,10-[3,4]epipyrroloanthracene-12,14(13H,15H)-dione
• 英文别名: 4-hydroxy-2-methyl-3a,4,9,9a-tetrahydro-4,9[1',2']benzeno-1H-benz[f]isoindole-1,3(2H)-dione；(15R,19R)-1-hydroxy-17-methyl-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
• 化学式: C₁₉H₁₅NO₃
• 分子量: 305.333
• InChiKey: JYJCOMSKUPTVBL-BHEGOAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (15R)-10-hydroxy-13-methyl-10,11-dihydro-9H-9,10-[3,4]epipyrroloanthracene-12,14(13H,15H)-dione
  参考文献：
  名称：

  Sapre, Jai V.; Khose, Vaibhav N.; Tawde, Trupti S., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2020, vol. 59, # 1, p. 93 - 101

  摘要：

  DOI：

文献信息

• Enantioselective Diels–Alder reaction of anthrone and maleimide catalyzed by a simple chiral tertiary amine
  作者：Jian-Fei Bai、Yun-Long Guo、Lin Peng、Li-Na Jia、Xiao-Ying Xu、Li-Xin Wang

  DOI：10.1016/j.tet.2012.11.011

  日期：2013.1

  Simple chiral tertiary amines with a special imide skeleton were first successfully applied to catalyze the enantioselective D–A reaction of anthrone and maleimides in excellent yields (up to 96%) and enantioselectivities (up to 95% ee).

  带有特殊酰亚胺骨架的简单手性叔胺首次成功地用于催化蒽酮和马来酰亚胺的对映选择性D-A反应，具有极高的收率（高达96％）和对映选择性（高达95％ee）。
• Ionic liquid promoted Diels-Alder Reaction between anthrone and maleimides
  作者：Nitin Mirgane、Sandip Kotwal、Anil Karnik

  DOI：10.2478/s11532-009-0136-6

  日期：2010.4.1

  Ionic liquids (IL) are gaining importance as green solvents. Imidazolium ionic liquid [bmim]+[Cl]−, an environmentally benign solvent, was found to promote the Diels-Alder reaction between anthrone and maleimides at room temperature with excellent yields. The ionic liquid played a dual role as solvent and catalyst.

  离子液体（IL）作为绿色溶剂正变得越来越重要。发现咪唑鎓离子液体[bmim] + [Cl] -（一种对环境有益的溶剂）在室温下以优异的产率促进蒽酮和马来酰亚胺之间的Diels-Alder反应。离子液体起着溶剂和催化剂的双重作用。
• Chiral primary amino alcohol organobase catalysts for the asymmetric Diels–Alder reactions of anthrones with maleimides
  作者：Jun Kumagai、Teppei Otsuki、U.V. Subba Reddy、Yoshihito Kohari、Chigusa Seki、Koji Uwai、Yuko Okuyama、Eunsang Kwon、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1016/j.tetasy.2015.10.022

  日期：2015.12

  Simple chiral triethylsilyl-amino alcohol organocatalysts containing a bulky triethylsilyl group on the oxygen atom at the gamma-position were designed and synthesized as new organocatalysts for enantioselective Diels-Alder reactions of anthrones with maleimides to produce chiral hydroanthracene Diels-Alder adducts in up to 99% yield and with up to 94% ee. (c) 2015 Elsevier Ltd. All rights reserved.
• Reversal of enantioselectivity induced by the achiral part of an organocatalyst in a Diels–Alder reaction
  作者：Trupti S. Tawde、Swapnil J. Wagh、Jai V. Sapre、Vaibhav N. Khose、Purav M. Badani、Anil V. Karnik

  DOI：10.1016/j.tetasy.2016.01.002

  日期：2016.2
• Asymmetric cycloaddition of anthrone with N-substituted maleimides with C2-chiral pyrrolidines
  作者：Kyohei Tokioka、Satoshi Masuda、Tomomi Fujii、Yasuo Hata、Yukio Yamamoto

  DOI：10.1016/s0957-4166(96)00473-9

  日期：1997.1

  Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C-2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.