dihydrobotrydial | 54433-86-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: dihydrobotrydial
• 英文别名: dihydrobotrydal；[(1R,4R,7S,8S,9R,11S,12S)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.04,12]dodecan-11-yl] acetate
• CAS: 54433-86-2
• 化学式: C₁₇H₂₈O₅
• 分子量: 312.406
• InChiKey: QUGYVDURDBEQRB-CJNHKLDISA-N

物化性质

• 沸点：
  416.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dihydrobotrydial 在 硼氘化钠 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以53%的产率得到C₁₇H₂₉⁽²⁾HO₅
  参考文献：
  名称：

  Studies on the biosynthesis of secobotryane skeleton

  摘要：

  The labelling and coupling patterns of secobotrytrienediol, biosynthesised from [1-C-13] and [1,2-C-13(2)]-acetate by the fungus Botrytis cinerea. have been used to define the mode of formation and the biogenetic origin of secobotrytrienediol. [10-H-2]-Botrydiol was not incorporated into the secobotryane skeleton. In addition, this feeding experiment led to the isolation of three new unlabelled derivatives possessing a secobotryane skeleton, secobotrydiene-3,10,15-triol, secobotrydiene-3,4,10,15-tetraol, and secobotrytriene-10,12,15-triol. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01025-1
• 作为产物：
  描述：

  2β-methoxyclovan-9-one 以 水 为溶剂， 反应 480.0h， 生成 dihydrobotrydial
  参考文献：
  名称：

  The Biotransformation of Some Clovanes by Botrytis cinerea

  摘要：

  The metabolism of the fungistatic agent 2 beta-methoxyclovan-9 alpha-ol (2) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 2 yielded compounds 3-5, 7, and 9. The major metabolites of compound 2 each show much reduced biological activity when compared with the parent compound. Also studied were the effects of B. cinerea on the metabolism of the related compounds 2 beta-methoxyclovan-9-one (3), 2 beta-methoxyclovan-9 beta-ol (4), and clovan-2,9-dione (6). Compounds 3, 4, 8, and 9 are described for the first time.

  DOI：

  10.1021/np9801054

文献信息

• Botrylactone: new interest in an old molecule—review of its absolute configuration and related compounds
  作者：Javier Moraga、Cristina Pinedo、Rosa Durán-Patrón、Isidro G. Collado、Rosario Hernández-Galán

  DOI：10.1016/j.tet.2010.11.022

  日期：2011.1

  The absolute configuration of botrylactone, a unique compound with an interesting polyketide lactone skeleton with two oxirane bridges previously isolated from Botrytis cinerea and described as a powerful antibiotic, has been reviewed on the basis of sign of the optical rotation, NOE experiments and NMR method. The isolation of 7-deoxybotrylactone and 5-hydroxy-7-(4-hydroxydec-2(3)-enoyl) botrylactone

  旋光性，NOE实验和NMR方法已对Botrylactone的绝对构型进行了综述，Botrylactone是具有有趣的聚酮内酯骨架和两个环氧乙烷桥的独特化合物，以前曾从灰葡萄孢菌中分离出来，被描述为强效抗生素。7-脱氧硼酸内酯和5-羟基-7-（4-羟基癸-2（3）-烯酰基）硼酸内酯的分离使我们能够用这种有趣的聚酮化合物骨架表征一个有趣的新化合物家族。提出了一种常见的与植物素衍生物的生物合成来源。
• Metabolites from a shake culture of Botrytis cinerea
  作者：Isidro G. Collado、Rosario Hernández-Galán、Rosa Durán-Patrón、Jesús M. Cantoral

  DOI：10.1016/0031-9422(94)00690-u

  日期：1995.2

  Abstract Four new metabolites, 10-oxo-dihydrobotrydial, 4β-acetoxy-9β-10β-15α-trihydroxyprobotrydial, β - O -methyldihydrobotrydialone and α - O -methyldihydrobotrydialone, were isolated from a shake culture of Botrytis cenerea . The second compound, a tricyclic sesquiterpene, is a key biosynthetic intermediate and sheds light on the last steps of the biosynthesis of botrydial derivatives. A higher

  摘要 从 Botrytis cenerea 的振荡培养物中分离出四种新的代谢物，10-oxo-dihydrobotrydial、4β-acetoxy-9β-10β-15α-trihydroxyprobotrydial、β-O-methyldihydrobotrydialone 和 α-O-methyldihydrobotrydialone。第二种化合物是三环倍半萜烯，是一种关键的生物合成中间体，揭示了葡萄二醛衍生物生物合成的最后一步。在分离的代谢物中观察到更高的氧化水平。通过对天然化合物及其衍生物的广泛 NMR 研究阐明了结构。
• Bradshaw, A. Peter W.; Hanson, James R.; Nyfeler, Robert, Journal of the Chemical Society. Perkin transactions I, 1982, # 9, p. 2187 - 2192
  作者：Bradshaw, A. Peter W.、Hanson, James R.、Nyfeler, Robert、Sadler, Ian H.

  DOI：——

  日期：——
• Biotransformation of Bioactive Isocaryolanes by <i>Botrytis cinerea</i>
  作者：Jociani Ascari、Maria Amélia Diamantino Boaventura、Jacqueline Aparecida Takahashi、Rosa Durán-Patrón、Rosario Hernández-Galán、Antonio J. Macías-Sánchez、Isidro G. Collado

  DOI：10.1021/np1009465

  日期：2011.8.26

  The metabolism of the fungistatic agent (8R,9R)-8-methoxyisocaryolan-9-ol (4) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 4 yielded compounds 5 and 6-9. No dihydrobotrydial is observed after 4 days of incubation of compound 4. Separate biotransformation of (8R,9R)-isocaryolane-8,9-diol (5) yielded compounds 7-11. The evaluation of the fungistatic activity against B. cinerea of compounds 4, 5, and 6 is reported. (4R,8R,9R)-8-Methoxyisocaryolane-9,15-diol (6), a major metabolite of (8R,9R)-8-methoxyisocaryolan-9-ol (4), shows a much reduced biological activity when compared with the parent compound. Isocaryolane derivatives 6-11 are described for the first time.
• Kimura, Yasuo; Fujioka, Hiroaki; Nakajima, Hiromitsu, Agricultural and Biological Chemistry, 1988, vol. 52, # 7, p. 1845 - 1848
  作者：Kimura, Yasuo、Fujioka, Hiroaki、Nakajima, Hiromitsu、Hamasaki, Takashi、Isogai, Akira

  DOI：——

  日期：——