lactarorufin A | 35008-20-9

• 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
• 英文名称: lactarorufin A
• 英文别名: (5S,5aS,8aR,9S)-5,9-dihydroxy-5,7,7-trimethyl-4,5a,6,8,8a,9-hexahydro-1H-azuleno[5,6-c]furan-3-one
• CAS: 35008-20-9
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: UUZWMJQAEYBHAO-ZFVXVEAMSA-N

物化性质

• LogP：
  1.270 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  lactarorufin A 在 吡啶 、 二异丁基氢化铝 作用下， 反应 4.0h， 生成 furanether A
  参考文献：
  名称：

  3,8-Ethers of lactarane sesquiterpenes

  摘要：

  An ethanol extract of Lactarius necator gave 3,8-oxa-13-hydroxy-lactar-6-en-5-oic acid gamma-lactone and furanether A, besides other known sesquiterpenes. Syntheses of these internal ethers, as well as the 13-oxa-lactonic analogue, were performed. The antifeedant properties of the internal ethers measured against the storage pests Tribolium confusum, Trogoderma granarium and Sitophylus granarius are reported.

  DOI：

  10.1016/0031-9422(93)85166-o
• 作为产物：
  描述：

  (1aα,3aβ,6aβ,6bα)-(+/-)-methyl 3a,4,5,6,6a,6b-hexahydro-5,5,6b-trimethyl-2<<(trifluoromethyl)sulfonyl>oxy>cyclopropindene-1a(1H)-carboxylate 在 palladium diacetate 硫酸 、 二甲基二环氧乙烷 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 6.0h， 生成 lactarorufin A
  参考文献：
  名称：

  Total synthesis of some marasmane and lactarane sesquiterpenes.

  摘要：

  A general and efficient synthetic route to the marasmane sesquiterpenes (+/-)-isovelleral (2) and (+/-)-stearoylvelutinal (1b) is described. Total syntheses of two other naturally occurring sesquiterpenes, deconjugated anhydrolactarorufin A (5) and lactarorufin A (6), were achieved using an acid-catalyzed ring expansion of lactone 25. All four syntheses are highly stereoselective and do not require the use of any protecting groups. Finally, the protic acid-catalyzed degradation of velutinal (1a) was investigated in an effort to chemically induce the biologically important conversion of velutinal (1a) to isovelleral (2). The experimental results thus obtained indicate that an enzymatic mechanism for the key transformation of velutinal (1a) into isovelleral (2) is more plausible than one that is acid-catalyzed.

  DOI：

  10.1021/jo00048a036

文献信息

• Kopczacki; Gumulka; Masnyk, Polish Journal of Chemistry, 2004, vol. 78, # 1, p. 89 - 108
  作者：Kopczacki、Gumulka、Masnyk、Sarosiek、Barycki、Ignacak、Zochowski、Grabarczyk、Nowak、Daniewski

  DOI：——

  日期：——
• Synthesis and antifeedant properties of N-benzoylphenylisoserinates of Lactarius sesquiterpenoid alcohols
  作者：Piotr Kopczacki、Maria Gumułka、Marek Masnyk、Halina Grabarczyk、Gerard Nowak、Włodzimierz M Daniewski

  DOI：10.1016/s0031-9422(01)00294-1

  日期：2001.11

  The esterification of various sesquiterpenoid alcohols of Luctarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol (R)) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium and Sitophylus granarius were measured. The introduction of the taxol side chain in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Daniewski, Wlodzimierz Maria; Kroszczynski, Wojciech; Krol, Jerzy, Polish Journal of Chemistry, 1983, vol. 57, # 4/5/6, p. 483 - 487
  作者：Daniewski, Wlodzimierz Maria、Kroszczynski, Wojciech、Krol, Jerzy

  DOI：——

  日期：——
• Daniewski, W. M.; Gomulka, M.; Ptaszynska, K., Polish Journal of Chemistry, 1992, vol. 66, # 5, p. 791 - 800
  作者：Daniewski, W. M.、Gomulka, M.、Ptaszynska, K.、Skibicki, P.、Jacobsson, U.、Norin, T.

  DOI：——

  日期：——
• DANIEWSKI, WLODZIMIERZ M.;GUMULKA, MARIA;PTASZYNSKA, KATARZYNA;KAMIENSKI,+, BULL. POL. ACAD. SCI. CHEM., 37,(1989) N-8, C. 289-295
  作者：DANIEWSKI, WLODZIMIERZ M.、GUMULKA, MARIA、PTASZYNSKA, KATARZYNA、KAMIENSKI,+

  DOI：——

  日期：——