8α-hydroxy-drimanoic acid | 139343-87-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8α-hydroxy-drimanoic acid
• 英文别名: 8α-hydroxydriman-11-oil acid；diaporol I；8-hydroxydrimanic acid；8-hydroxy-drimanoic acid-(11)；(4aS)-2c-Hydroxy-2t.5.5.8at-tetramethyl-(4arH)-decahydro-naphthoesaeure-(1t)；8-Hydroxy-drimansaeure-(11)；Diaporol I；(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalene-1-carboxylic acid
• CAS: 139343-87-6
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: VYGRCVWARMYZPO-IDTSFGKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8α-hydroxy-drimanoic acid 在 硫酸 作用下， 生成 (1S,4aS,8aS)-2,5,5,8a-四甲基-1,4,4a,5,6,7,8,8a-八氢萘-1-羧酸
  参考文献：
  名称：

  有关三萜的知识。第132部分。关于齐墩果酸和三萜烯安布林与二萜松香酸和马诺酚之间的连接

  摘要：

  这项工作描述了从五环三萜齐墩果酸（I）和三环三萜Ambreïn（IX）的环A和B萃取酸VI。Ambreïns的A和B环通过实验与双环二萜的Manool-Sclareol组（XV，XVI）的两个环相连。另外，证明了Manool-Sclareol基团的双环系统的结构与三环二萜的松香酸-右旋马来酸基团的环A和B的一致性。这种同一性不仅涉及环A和B的构成，而且还涉及提到的二萜和三萜的所有亚组中这两个环的结合处的空间结构，目前它们包括24种天然存在的代表：14种齐墩果酸-β-amyrin组

  DOI：

  10.1002/hlca.19480310639
• 作为产物：
  描述：

  (+)-drimane-8,11-diol 在 Jones reagent 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 以80%的产率得到8α-hydroxy-drimanoic acid
  参考文献：
  名称：

  Synthesis and bio-inspired optimization of drimenal: Discovery of chiral drimane fused oxazinones as promising antifungal and antibacterial candidates

  摘要：

  The synthesis of antifungal natural product drimenal was accomplished. Bio-inspired optimization protruded chiral 8-(R)-drimane fused oxazinone D as a lead, considering favorable physicochemical profiles for novel pesticides. The improved scalable synthesis of scaffold D was implemented by Hofmann rearrangment under mild conditions. Detailed structural optimization was discussed for both antifungal and antibacterial exploration. Substituted groups (SGs) with C-3 similar to C-5 hydrocarbon chain are recommended for exploration of antifungal agents, while substituents with C-4 similar to C-6 carbon length are preferred for antibacterial ingredients. The chiral drimane fused oxazinone D8 was selected as a promising antifungal candidate against Botrytis cirerea, with an EC50 value of 1.18 mg/L, with the enhancement of up to >25 folds and >80 folds than the mother compound D, and acyclic counterpart AB5, respectively. The in vivo bioassay confirmed much better preservative effect of D8 than that of Carbendazim. The chiral oxazinone variant D10 possessed prominent antibacterial activity, with MIC values of 8 mg/L against both Bacillus subtilis and Ralstonia solanacearum, showing advantages over the positive control streptomycin sulfate. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.051

文献信息

• Sulla costituzione degli eteri enolici dell'acetonossalato d'etile
  作者：A. Rossi、H. Schinz

  DOI：10.1002/hlca.19480310638

  日期：——

  a) Durch Behandlung von Acetonoxalester mit o-Ameisensäureester, Alkohol und Ammonchlorid nach der Vorschrift von Claisen entsteht nicht der α-Enoläther, wie der genannte Autor angibt, sondern das γ-Isomere.

  a）按照克莱森的说明，用邻甲酸酯，乙醇和氯化铵处理草酸丙酮，不会产生α-烯醇醚，如作者所言，而是γ-异构体。
• Vlad, P. F., Russian Journal of Physical Chemistry, 1992, vol. 66, # 4, p. 467 - 468
  作者：Vlad, P. F.

  DOI：——

  日期：——
• Investigation of the products of the ozonolysis of neoabienols
  作者：M. N. Koltsa、G. N. Mironov、A. N. Aryku、P. F. Vlad

  DOI：10.1007/bf00629827

  日期：——
• Absolute stereochemistry of natural sesquiterpenoid diacylglycerols
  作者：Nicon Ungur、Margherita Gavagnin、Angelo Fontana、Guido Cimino

  DOI：10.1016/s0957-4166(99)00119-6

  日期：1999.4

  The absolute stereochemistry of farnesic and drimenic glyceryl esters la-le and 2a-2b, previously isolated from marine dorid nudibranchs, has been established by their synthesis. (C) 1999 Elsevier Science Ltd. All rights reserved.