(15S)-13-benzyl-10-hydroxy-10,11-dihydro-9H-9,10-[3,4]epipyrroloanthracene-12,14(13H,15H)-dione | 354150-89-3

• 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: (15S)-13-benzyl-10-hydroxy-10,11-dihydro-9H-9,10-[3,4]epipyrroloanthracene-12,14(13H,15H)-dione
• 英文别名: 4-hydroxy-2-benzyl-3a,4,9,9a-tetrahydro-4,9[1',2']benzeno-1H-benz[f]isoindole-1,3(2H)-dione；4-hydroxy-2-benzyl-3a,4,9,9atetrahydro-4,9[1’,2’]-benzeno-1H-benz[f]isoindole-1,3(2H)-dione；(S,S)-(-)-4-hydroxy-2-benzyl-3a,4,9,9a-tetrahydro-4,9-[1',2']-benzeno-1H-benz[f]isoindole-1,3(2H)-dione；(15S,19S)-17-benzyl-1-hydroxy-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
• CAS: 354150-89-3
• 化学式: C₂₅H₁₉NO₃
• 分子量: 381.431
• InChiKey: RDRBIPVDFUGYAK-ZKKFKWFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (alphas)-(9ci)-alpha-甲基-1H-苯并咪唑-2-甲醇 在 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 (15S)-13-benzyl-10-hydroxy-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

• Asymmetric organocatalytic anthrone additions to activated alkenes
  作者：Alex Zea、Andrea-Nekane R. Alba、Natalia Bravo、Albert Moyano、Ramon Rios

  DOI：10.1016/j.tet.2011.02.032

  日期：2011.4

  Asymmetric organocatalytic additions of anthrones to activated alkenes are discussed. The reaction between anthrone or dithranol and α,β-unsaturated aldehydes is catalyzed by diphenylprolinol trimethylsilyl ether in toluene at −40 °C, giving the Michael adducts with good yields and enantioselectivities. Bifunctional amino-thioureas efficiently catalyze the additions of anthrones to both nitroalkenes and maleimides

  讨论了蒽酮向活化烯烃的不对称有机催化加成反应。在-40°C下，二苯基脯氨醇三甲基甲硅烷基醚在甲苯中催化蒽酮或二乙醇烷与α，β-不饱和醛之间的反应，从而使迈克尔加合物具有良好的收率和对映选择性。双官能氨基硫脲可有效地催化蒽酮向硝基烯烃和马来酰亚胺的添加，并且在室温下的两种情况下均可实现高对映选择性。在硝基烯烃的情况下，仅迈克尔加成发生。蒽酮通常与马来酰亚胺反应生成Diels–Alder环加合物，而二蒽酚则提供迈克尔加成物。
• 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）。
• A First Case of Asymmetric Catalysis Induced by Metal-Free Bisoxazolines
  作者：Deniz Akalay、Gerd Dürner、Michael W. Göbel

  DOI：10.1002/ejoc.200800179

  日期：2008.5

  Metal-free bisoxazolines catalyze the Diels–Alder reaction of N-substituted maleimides with anthrone derivatives leading to products in excellent yields and enantioselectivities up to 70 %. A mechanism relying on Bronsted-base catalysis is assumed to be involved with formation of an ion pair between the protonated catalyst and the anthrone enolate, which acts as a diene.(© Wiley-VCH Verlag GmbH & Co. KGaA

  不含金属的双恶唑啉可催化 N-取代马来酰亚胺与蒽酮衍生物的 Diels-Alder 反应，从而产生出色的产率和高达 70% 的对映选择性。假设依赖布朗斯台德碱催化的机制涉及质子化催化剂和作为二烯的蒽酮烯醇化物之间离子对的形成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany , 2008)
• 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