siderol | 19885-22-4

• 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: siderol
• 英文别名: [(1R,2S,4S,5S,9R,10S,13R)-5-(hydroxymethyl)-5,9,14-trimethyl-2-tetracyclo[11.2.1.01,10.04,9]hexadec-14-enyl] acetate
• CAS: 19885-22-4
• 化学式: C₂₂H₃₄O₃
• 分子量: 346.51
• InChiKey: OFNWUWHDGCNABD-CSGHFTSRSA-N

物化性质

• 熔点：
  152-153 °C
• 沸点：
  440.6±28.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  siderol 生成 [(1R,2S,4S,5S,9S,10R,13S)-5-(chloromethyl)-5,9,14-trimethyl-2-tetracyclo[11.2.1.01,10.04,9]hexadec-14-enyl] acetate
  参考文献：
  名称：

  FRAGA, BLAULIO M.;HERNANDEZ, MELCHOR G.;RODRIGUEZ, MANUEL D.;DIAZ, CARMEN+, PHYTOCHEMISTRY, 26,(1987) N 7, 1931-1934

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸酐 、 sideridiol diacetate 在 吡啶 作用下， 反应 24.0h， 生成 siderol
  参考文献：
  名称：

  Synthesis, Structural Characterization, Spectroscopic Properties, and Theoretical Investigation of Siderol Acetate

  摘要：

  In the present study, siderol acetate (1) was synthesized from siderol isolated from endemic Sideritis species, then its chemical structure was determined by using various spectroscopic methods (FT-IR, H-1 NMR, and C-13 NMR). The geometrical parameters, vibrational frequencies and gauge including atomic orbital (GIAO) H-1 and C-13 NMR chemical shift values for siderol acetate in the ground state have been calculated using the Density Functional Theory (DFT) and Hartree-Fock (HF) methods with the 6-31G(d) basis set. The calculated vibrational frequencies and H-1 and C-13 NMR chemical shifts have been compared with experimental values. A combined study based on NMR data and quantum-mechanical calculations using DFT/GIAO indicate that 1 is the correct structure of the title molecule.

  DOI：

  10.1134/s0036024419130235

文献信息

• Transformation of ent-kaur-15-enes by Gibberella fujikuroi
  作者：Carmen E. Diaz、Pedro Gonzalez、James R. Hanson、Braulio M. Fraga、Melchor G. Hernandez、Manuel D. Rodriguez

  DOI：10.1016/s0031-9422(00)81732-x

  日期：——

  Abstract The microbiological transformation of ent -kaur-15-ene and of some derivatives by Gibberella fujikuroi into the gibberell-15-ene analogues of GA 3 , GA 7 , GA 13 and GA 16 and into 7,18-dihydroxykaur-15-enolide and the Δ 15 -isomer of fujenal is described.

  摘要 藤黑赤霉 ent -kaur-15-ene 和一些衍生物在微生物学上转化为 GA 3 、GA 7 、GA 13 和 GA 16 的赤霉素 15-ene 类似物和 7,18-dihydroxykaur-15-enolide并且描述了fujenal的Δ 15 -异构体。
• Diterpenes from sideritis sicula ucria
  作者：F. Piozzi、P. Venturella、A. Bellino、R. Mondelli

  DOI：10.1016/0040-4020(68)88169-4

  日期：1968.1

  Two new diterpenes, sideridiol C20H32O2 and siderol C22H34O3 were extracted from the corols of Sideritis sicula Ucria (Fam. Labiatae). Their structures were elucidated as I and IX, respectively, and the absolute configuration was proved to be related to (−)-isokaurene.

  从Sideritis sicula Ucria（Fam。Labiatae）的提取物中提取了两个新的二萜，铁三糖醇C 20 H 32 O 2和铁氧烷C 22 H 34 O 3。它们的结构分别被阐明为I和IX，并且绝对构型被证明与（-）-异kaurene有关。
• GARCIA-GRANADOS, ANDRESS;MARTINEZ, ANTONIO;ORTIZ, ANTONIO;ONORATO, MARIA +, J. NATUR. PROD., 53,(1990) N, C. 441-450
  作者：GARCIA-GRANADOS, ANDRESS、MARTINEZ, ANTONIO、ORTIZ, ANTONIO、ONORATO, MARIA +

  DOI：——

  日期：——