4-(4'-{[(3-羟基-3,4-二氢-2H-1,5-苯并二氧杂卓-3-基)甲基]硫基}-4-联苯基)-2,4-二氧代丁酸 | 88197-30-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 4-(4'-{[(3-羟基-3,4-二氢-2H-1,5-苯并二氧杂卓-3-基)甲基]硫基}-4-联苯基)-2,4-二氧代丁酸
• 英文名称: robustadial A
• 英文别名: robustadial B；robustadial；(1'R,2R,4R,5'S)-5,7-dihydroxy-6',6'-dimethyl-4-(2-methylpropyl)spiro[3,4-dihydrochromene-2,2'-bicyclo[3.1.1]heptane]-6,8-dicarbaldehyde
• CAS: 88197-30-2
• 化学式: C₂₃H₃₀O₅
• 分子量: 386.488
• InChiKey: SULUCYRQUAHFJK-DOGSQSLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4'-{[(3-羟基-3,4-二氢-2H-1,5-苯并二氧杂卓-3-基)甲基]硫基}-4-联苯基)-2,4-二氧代丁酸 生成 robustadial A dimethyl ether
  参考文献：
  名称：

  SALOMON, ROBERT G.;LAL, KASTURI;MAZZA, SAMUEL M.;ZARATE, EUGENE A.;YOUNGS+, J. AMER. CHEM. SOC., 110,(1988) N 15, 5213-5214

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,2'R,4'S)-5,7-dihydroxy-3',3'-dimethyl-2',4'-methanospiro-4-one 在 palladium on activated charcoal 硫酸 、 氢气 、 四氯化钛 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 4-(4'-{[(3-羟基-3,4-二氢-2H-1,5-苯并二氧杂卓-3-基)甲基]硫基}-4-联苯基)-2,4-二氧代丁酸
  参考文献：
  名称：

  The Synthesis of (-)-Robustadial A and Some Analogues.

  摘要：

  The naturally occurring chroman derivative, robustadial A, and several analogues have been prepared by a four-step synthesis starting from phloroglucinol. The synthetic scheme involves as the first step a Friedel-Crafts condensation of an alpha,beta-unsaturated acid derivative with phloroglucinol to the corresponding chromanone. The isobutyl group at the 4-position was introduced with methallylzine bromide followed by hydrogenation, carried out as a one-pot reaction. Finally, both aldehyde functions were attached using dichloromethyl methyl ether and titanium tetrachloride. Optically pure 6,6-dimethylbicyclo[3.1.1]heptan-2-ylidene-acetic acid, needed for the synthesis of robustadial, was prepared from (-)-nopol by two consecutive oxidations in 77% overall yield.

  DOI：

  10.3891/acta.chem.scand.50-0132

文献信息

• Plants extracts for use in brain modulation
  申请人：InterMed Discovery GmbH

  公开号：EP1939166A1

  公开（公告）日：2008-07-02

  Compounds obtainable from plants, e.g. of the genus Eucalyptus, or from microorganisms are shown to be useful as CNS activity modulators useful e.g. in the treatment of depression, for lifting mood and/or for increasing behavioural initiative and the like. This use and related aspects form embodiments of the invention. Also compounds as such are presented. The compounds useful are acylphloroglucine derivatives of the formula I, wherein the substituents are as defined in the description.

  从植物（如桉树属）或微生物中提取的化合物可用作中枢神经系统活性调节剂，例如用于治疗抑郁症、改善情绪和/或提高行为主动性等。这种用途和相关方面构成了本发明的实施例。此外，还介绍了本发明的化合物。 有用的化合物是式 I 的酰基氯葡萄糖衍生物、 其中的取代基如描述中所定义。
• Total synthesis establishing the correct structures of robustadials A and B. Reinterpretation of NMR data
  作者：Robert G. Salomon、Samuel M. Mazza、Kasturi Lal

  DOI：10.1021/jo00268a016

  日期：1989.3
• A two-step biomimetic synthesis of antimalarial robustadials A and B
  作者：Sandip B. Bharate、Inder Pal Singh

  DOI：10.1016/j.tetlet.2006.07.113

  日期：2006.9

  The antimalarial robustadials A and B have been synthesized in two steps starting from commercially available phloroglucinol comprising a key biomimetic three-component reaction that involves in situ generation of an o-quinone methide via Knoevenagel condensation and subsequent Diels-Alder cycloaddition with (-)-beta-pinene. @ 2006 Elsevier Ltd. All rights reserved.
• SALOMON, ROBERT G.;MAZZA, SAMUEL M.;LAL, KASTURI, J. ORG. CHEM., 54,(1989) N, C. 1562-1570
  作者：SALOMON, ROBERT G.、MAZZA, SAMUEL M.、LAL, KASTURI

  DOI：——

  日期：——
• PLANTS EXTRACTS FOR USE IN BRAIN MODULATION
  申请人：Roemer Ernst

  公开号：US20110021613A1

  公开（公告）日：2011-01-27

  Compounds obtainable from plants, e.g. of the genus Eucalyptus , or from microorganisms are shown to be useful as CNS activity modulators useful e.g. in the treatment of depression, for lifting mood and/or for increasing behavioural initiative and the like. This use and related aspects form embodiments of the invention. Also compounds as such are presented. The compounds useful are acylphloroglucine derivatives of the formula I, wherein the substituents are as defined in the description.