3-isobutyl-4-{4-[(3-methyl-2-butenyl)oxy]phenyl}-1H-pyrrole-2,5-dione | 656830-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-isobutyl-4-{4-[(3-methyl-2-butenyl)oxy]phenyl}-1H-pyrrole-2,5-dione
• 英文别名: 3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]-1H-pyrrole-2,5-dione；3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]-1H-pyrrol-2,5-dione；3-[4-(3-methylbut-2-enyloxy)phenyl]-4-isobutylpyrrole-2,5-dione；Antrodin B；camphorataimide B；3-[4-(3-Methylbut-2-enoxy)phenyl]-4-(2-methylpropyl)pyrrole-2,5-dione
• CAS: 656830-25-0
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: AILGRWSIRAPLCJ-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  475.8±45.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-isobutyl-4-{4-[(3-methyl-2-butenyl)oxy]phenyl}-1H-pyrrole-2,5-dione 在 sodium tetrahydroborate 、 nickel diacetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 (+/-)-cis-3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolidine-2,5-dione 、 (+/-)-trans-3-isobutyl-4-[4-(3-methyl-2-butenyloxy)phenyl]pyrrolidine-2,5-dione
  参考文献：
  名称：

  Total synthesis of (±)-camphorataimides and (±)-himanimides by NaBH4/Ni(OAc)2 or Zn/AcOH stereoselective reduction

  摘要：

  Maleic anhydride 1 of Antrodia camphorate, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only five steps, in 40% overall yield from commercially available succinic anhydride. The crucial antrodimides 3 and 2 can be readily transformed by the chemoselective reduction with Zn/AcOH and NaBH(4)/Ni(OAc)(2).4H(2)O to afford the naturally occurring camphorataimides, 4 and 5, in high yields as well, respectively. This synthetic strategy can also be modified to give access to a variety of different maleic acid derivatives, himanimides 6-8. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.077
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium tert-butylate 、 水 、 二甲基二环氧乙烷 、 potassium carbonate 、 戴斯-马丁氧化剂 、 三乙胺 、 N,N-二异丙基乙胺 、 六甲基二硅氮烷 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 102.92h， 生成 3-isobutyl-4-{4-[(3-methyl-2-butenyl)oxy]phenyl}-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Unified route to asymmetrically substituted butenolide, maleic anhydride, and maleimide constituents of Antrodia camphorata

  摘要：

  The first synthesis of antrocinnamomin D and a new synthesis of antrodins A and B have been achieved in 6-8 steps and high overall efficiency (51, 46, and 43%, respectively) from commercially available methyl 4-hydroxyphenylacetate. Key steps include Furstner-Kochi iron-catalyzed sp(2)-sp(3) cross-coupling and 2-silyloxyfuran oxyfunctionalization. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.09.064

文献信息

• Enzymatic <i>O</i> ‐Prenylation of Diverse Phenolic Compounds by a Permissive <i>O</i> ‐Prenyltransferase from the Medicinal Mushroom <i>Antrodia camphorata</i>
  作者：Junbin He、Zhimin Hu、Zeyuan Dong、Bin Li、Kuan Chen、Zhanpeng Shang、Meng Zhang、Xue Qiao、Min Ye

  DOI：10.1002/adsc.201901396

  日期：2020.2.6

  Prenylated compounds are pharmacologically attractive natural products that are widely distributed in nature. Prenyltransferases (PTs) could catalyze the transfer of prenyl moieties to aromatic acceptors and increase the structural diversity and biological activity of natural products. In this work, a permissive O‐prenyltransferase AcaPT was discovered from Antrodia camphorata, a precious medicinal

  烯丙基化的化合物是在自然界中广泛分布的具有药理吸引力的天然产物。异戊二烯基转移酶（PTs）可以催化异戊二烯基团向芳族受体的转移，并增加天然产物的结构多样性和生物活性。在这项工作中，从台湾珍贵的香菇樟芝中发现了一种允许的邻戊二烯基转移酶AcaPT 。AcaPT对结构多样的药物样酚类化合物（包括Antrodins，类黄酮和香豆素）表现出强大的O-异戊二烯化能力。通过放大酶促合成，总共获得了23种O-异戊烯化产品。AcaPT可用作合成O的有效生物催化剂用于药物开发的异戊二烯基衍生物。
• COMPOUNDS FROM ANTRODIA CINNAMOMEA AND USE THEREOF
  申请人：SIMPSON BIOTECH CO., LTD.

  公开号：US20130225649A1

  公开（公告）日：2013-08-29

  The present invention relates to compounds from Antrodia cinnamomea . The present invention also relates to a composition and a method for treating or prophylaxis of hepatitis C virus (HCV) or human immunodeficiency virus (HIV) infection.

  本发明涉及来自红树菇的化合物。本发明还涉及一种用于治疗或预防丙型肝炎病毒（HCV）或人类免疫缺陷病毒（HIV）感染的组合物和方法。
• [EN] COMPOUNDS FROM MYCELIUM OF ANTRODIA CINNAMOMEA AND USE THEREOF<br/>[FR] COMPOSÉS ISSUS DE MYCÉLIUM D'ANTRODIA CINNAMOMEA ET LEUR UTILISATION
  申请人：SIMPSON BIOTECH CO LTD

  公开号：WO2009094807A1

  公开（公告）日：2009-08-06

  The present invention relates to compounds from mycelium of Antrodia cinnamomea. The present invention also relates to a composition and a method for treating or prophylaxis of hepatitis C virus (HCV) infection.

  本发明涉及来自红树菇菌丝体的化合物。本发明还涉及一种用于治疗或预防丙型肝炎病毒（HCV）感染的组合物和方法。
• Compounds isolated from antrodia cinnamomea and use thereof
  申请人：Sheu Chia-Chin

  公开号：US20100210865A1

  公开（公告）日：2010-08-19

  The present invention relates to novel compounds from Antrodia cinnamomea and their use.

  本发明涉及来自红树瘤菌的新化合物及其用途。
• Novel mixture and compounds from mycelia of Antrodia camphorata and use thereof
  申请人：Hattori Masao

  公开号：US20050197384A1

  公开（公告）日：2005-09-08

  The present invention relates to novel mixture and maleic and succinic acid derivatives from mycelium of Antrodia Camphorata and the medical use thereof. The present invention relates to the composition or mycelium comprising the compounds of the invention.

  本发明涉及从樟芝菌丝体中获得的马来酸和琥珀酸衍生物的新混合物及其医药用途。本发明涉及包括本发明化合物的菌丝体组合物。