4-hydroxy-2-methyl-3a,4,9,9a-tetrahydro-4,9[1',2']-benzeno-1H-benz[f]isoindole-1,3(2H)-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: 4-hydroxy-2-methyl-3a,4,9,9a-tetrahydro-4,9[1',2']-benzeno-1H-benz[f]isoindole-1,3(2H)-dione
• 英文别名: (15S,19S)-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-YJTLQXIOSA-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：

  N-甲基马来酰亚胺 、 蒽酮 在 (1R,2R)-N,N-dimethyl-N'-phthaloyl-1,2-diaminocyclohexane 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以47%的产率得到
  参考文献：
  名称：

  简单手性叔胺催化的蒽酮和马来酰亚胺的对映选择性狄尔斯-阿尔德反应

  摘要：

  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）。

  DOI：

  10.1016/j.tet.2012.11.011

文献信息

• 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.
• Sapre, Jai V.; Khose, Vaibhav N.; Tawde, Trupti S., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, <hi>2020</hi>, vol. 59, # 1, p. 93 - 101
  作者：Sapre, Jai V.、Khose, Vaibhav N.、Tawde, Trupti S.、Wagh, Swapnil J.、Karnik, Anil V.

  DOI：——

  日期：——