1β,4β-dihydroxy-6β-acetoxy-eudesmane | 95457-12-8

• 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: 1β,4β-dihydroxy-6β-acetoxy-eudesmane
• 英文别名: 6β-acetoxy-1β,4β-hydroxyeudesmane；[(1R,2S,4aR,5R,8S,8aS)-5,8-dihydroxy-4a,8-dimethyl-2-propan-2-yl-1,2,3,4,5,6,7,8a-octahydronaphthalen-1-yl] acetate
• CAS: 95457-12-8
• 化学式: C₁₇H₃₀O₄
• 分子量: 298.423
• InChiKey: PGMDYJUEXIFZJG-MDOLAMBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  1β,4β-dihydroxy-6β-acetoxy-eudesmane 在 吡啶 、 甲醇 、 sodium hydroxide 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 29.5h， 生成 1β-acetoxy-4β,6β-diisopropylidenedioxy-eudesman
  参考文献：
  名称：

  来自两个亚种的倍半萜烯

  摘要：

  摘要 除了先前报道的二萜外，Sideritis varoi 的两个亚种还提供了以下一系列新的eudesmane 和eudesmene 醋酸盐：1β-羟基-6β-乙酰氧基-eudesm-4(15)-ene；1β-羟基-6β-乙酰氧基-eudesm-4(15)-烯；1β,4β-dihydroxy-6β-acetoxy-eudesmane; 1β-羟基-6β-乙酰氧基-eudesm-3-烯；1β-羟基-6β-乙酰氧基-eudesm-4-ene。通过化学和光谱手段阐明了这些化合物的结构。

  DOI：

  10.1016/s0031-9422(00)80815-8
• 作为产物：
  描述：

  4β,5α-epoxy-6β-acetoxy-trans-germacr-1(10)-ene 、 溶剂黄146 以 水 为溶剂， 反应 15.0h， 以10 mg的产率得到1β,4β-dihydroxy-6β-acetoxy-eudesmane
  参考文献：
  名称：

  Biomimet1c cyclization of 4β, 5α-epoxy-6β-acetoxy--germacr-1(10)-ene to form -( 1β-h ; 5β-h)-guaianes

  摘要：

  DOI：

  10.1016/s0040-4020(01)87404-4

文献信息

• Chemical-Microbiological Synthesis of Cryptomeridiol Derivatives by <i>Gliocladium </i><i>r</i><i>oseum</i>:  Semisynthesis of 11-Hydroxyeudesmanolides
  作者：Andrés García-Granados、María C. Gutiérrez、Andrés Parra、Francisco Rivas

  DOI：10.1021/np010631m

  日期：2002.7.1

  Biotransformations of 4alpha- and 4beta-hydroxyeudesmane derivatives by the filamentous fungus Gliocladium roseum were achieved. Hydroxylation at C-11 was the main action of this microorganism, producing new cryptomeridiol (12 and 14) and 4-epi-cryptomeridiol derivatives (6 and 7), respectively, in good yields. The biotransformation activity of G. roseum toward 4beta-hydroxyeudesmane was focused on

  通过丝状真菌Gliocladium roseum实现了4alpha-和4beta-hydroxyeudesmane衍生物的生物转化。C-11处的羟基化作用是该微生物的主要作用，分别以高收率生产出新的隐美二醇（12和14）和4-表-隐美二醇衍生物（6和7）。迷迭香对4β-羟基eudesmane的生物转化活性集中在异丙基部分，但更多地分散在4α-羟基化衍生物上，既作用于分子的“ A”环，又影响“ B”环和异丙基。从分离的11，12-二羟基化代谢产物中半合成11-羟基马来酸酐也被完成，并用于指定羟基化的立体化学。
• Improved microbiological hydroxylation of sesquiterpenoids: semisynthesis, structural determination and biotransformation studies of cyclic sulfite eudesmane derivatives
  作者：Andrés García-Granados、María C. Gutiérrez、Francisco Rivas

  DOI：10.1039/b301577g

  日期：——

  Two new cyclic sulfite eudesmane derivatives have been investigated. Their (R) and (S) sulfur configuration and the structural arrangement of their "A" rings have been assigned by means of their 13C and 1H NMR chemical shifts and have been confirmed by single-crystal X-ray analyses. Microbial-transformation of these epimer cyclic sulfites and their dihydroxyeudesmane precursor have been studied using

  已经研究了两种新的环状亚硫酸盐奥德斯曼衍生物。它们的（R）和（S）硫构型及其“ A”环的结构排列已通过其13C和1H NMR化学位移进行了指认，并已通过单晶X射线分析得到证实。已使用羟基化真菌黑根霉（Rhizopus nigricans）研究了这些差向异构体环状亚硫酸盐及其二羟基Eudesmane前体的微生物转化。已经发现两种环亚硫酸盐阿联苯醚的生物催化速率提高和生物转化的显着差异。从（S）-非对映异构体的生物转化中分离出有希望的8alpha，11-二羟基衍生物。
• Biotransformation of 4β-hydroxyeudesmane-1,6-dione by Gliocladium roseum and Exserohilum halodes
  作者：Andrés Garcı́a-Granados、Marı́a C. Gutiérrez、Francisco Rivas、José M. Arias

  DOI：10.1016/s0031-9422(01)00340-5

  日期：2001.11

  Biotransformation of sesquiterpene 4 beta -hydroxyeudesmane-1,6-dione by the filamentous fungi Gliocladium roseum and Exserohilum halodes was achieved. With Exserohilum halodes, only one metabolite was obtained, as a result of the regio- and stereoselective reduction of the keto group at C-1, which is difficult to achieve by chemical means. Five metabolites were produced with Gliocladium roseum, three of which, the 7 alpha -hydroxylated, the 7 alpha, 11- and the 1 alpha ,8 alpha -dihydroxylated derivatives, have not previously been reported, The hydroxylation at C-1 I is the main action of this microorganism, These 11-hydroxylated compounds can be chemically transformed into 6 beta ,12-eudesmanolides. (C) 2001 Published by Elsevier Science Ltd.
• GARCIA-GRANADOS, ANDRES;MARTINEZ, ANTONIO;ONORATO, ESTHER;RIVAS, FRANCISC+, TETRAHEDRON, 47,(1991) N, C. 91-102
  作者：GARCIA-GRANADOS, ANDRES、MARTINEZ, ANTONIO、ONORATO, ESTHER、RIVAS, FRANCISC+

  DOI：——

  日期：——
• ARIAS, J. M.;GARCIA-GRANADOS, A.;MARTINEZ, A.;ORONATO, M. E.;RIVAS, F., TETRAHEDRON LETT., 29,(1988) N 35, C. 4471-4472
  作者：ARIAS, J. M.、GARCIA-GRANADOS, A.、MARTINEZ, A.、ORONATO, M. E.、RIVAS, F.

  DOI：——

  日期：——