furandiol | 59684-34-3

• 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: furandiol
• 英文别名: (5S,5aS,8aR,9S)-5,7,7-trimethyl-4,5a,6,8,8a,9-hexahydroazuleno[5,6-c]furan-5,9-diol
• CAS: 59684-34-3
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: CJMRDWKLOVHYSM-HTUGSXCWSA-N

物化性质

• 沸点：
  303.7±31.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  furandiol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Kopczacki; Gumulka; Masnyk, Polish Journal of Chemistry, 2004, vol. 78, # 1, p. 89 - 108

  摘要：

  DOI：
• 作为产物：
  描述：

  (4aR,7aS,8S)-8-Hydroxy-6,6,8-trimethyl-5,6,7,7a,8,9-hexahydro-4aH-2-oxa-cyclopenta[f]azulen-4-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以24%的产率得到8-epi-furandiol
  参考文献：
  名称：

  Daniewski, W. M.; Gluzinski, P.; Gumulka, M., Polish Journal of Chemistry, 1994, vol. 68, # 2, p. 287 - 296

  摘要：

  DOI：

文献信息

• Synthesis of N-Acetyl-3-phenylisoserinates of Sesquiterpenoid Alcohols of Lactarius Origin
  作者：Rafał Barycki、Maria Gumułka、Marek Masnyk、Włodzimierz M. Daniewski、Mirosław Kobus、Mirosław Łuczak

  DOI：10.1135/cccc20020075

  日期：——

  Important biological properties of Taxol i.e. 13-N-benzoyl-(2R,3S)-3-phenylisoserinate of baccatin III and also N-benzoyl-(2R,3S)-3-phenylisoserinates of several sesquiterpenoid alcohols of Lactarius origin prompted us to synthesize N-acetyl-3-phenylisoserinates of latter alcohols in order to check and compare their biological properties. Suitably protected phenylisoserine 5 when reacted with sesquiterpenoid alcohols in the presence of DCC gave appropriate esters 7. These, after catalytic hydrogenation deprotection produced aminols 8, which were acetylated and gave the required N-acetyl-3-phenylisoserinates 9a-9g.

  紫杉醇的重要生物学特性，即紫杉醇III的13-N-苯甲酰-(2R,3S)-3-苯基异丝氨酸和几种乳牛肝菌源的倍半萜醇的N-苯甲酰-(2R,3S)-3-苯基异丝氨酸，促使我们合成后者醇的N-乙酰基-3-苯基异丝氨酸以检查和比较它们的生物学特性。适当保护的苯基异丝氨酸5在DCC存在下与倍半萜醇反应，生成适当的酯7。这些酯经过催化氢解去保护后，产生氨醇8，随后乙酰化并产生所需的N-乙酰基-3-苯基异丝氨酸9a-9g。
• Sesquiterpenes from Russula sardonia
  作者：Daniela Andina、Maria de Bernardi、Alessandra del Vecchio、Giovanni Fronza、Giorgio Mellerio、Giovanni Vidari、Paola Vita-Finzi

  DOI：10.1016/0031-9422(80)85020-5

  日期：1980.1

  Abstract Three new sesquiterpenes, furanether A, furosardonin A and sardonialactone A (7-hydroxyblennin A), together with lactaral, vellerolactone, two known furan alcohols, lactarorufin A and cerevisterol, were isolated from Russula sardonia . Structures and stereochemistry were elucidated by spectral data and correlation to known compounds by chemical transformations.

  摘要 从红菇中分离到了三种新的倍半萜，呋喃醚 A、呋喃沙酮 A 和 sardonialactone A (7-hydroxyblennin A)，以及乳醛、velerolactone、两种已知的呋喃醇乳妥鲁芬 A 和 cerevisterol。通过光谱数据和通过化学转化与已知化合物的相关性来阐明结构和立体化学。
• 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.
• Total synthesis of some marasmane and lactarane sesquiterpenes.
  作者：Scott K. Thompson、Clayton H. Heathcock

  DOI：10.1021/jo00048a036

  日期：1992.10

  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.
• Biogenesis-like conversion of marasmane to lactarane and seco-lactarane skeleton
  作者：Maria De Bernardi、Giovanni Vidari、Paola Vita-Finzi、Katia Gluchoff Fiasson

  DOI：10.1016/s0040-4039(00)85670-1

  日期：1982.1