acremine O | 1448507-15-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acremine O
• 英文别名: Acremine O；(3R,5R)-7-chloro-3-hydroxy-2,2,8-trimethyl-1-oxaspiro[4.5]dec-7-ene-6,9-dione
• CAS: 1448507-15-0
• 化学式: C₁₂H₁₅ClO₄
• 分子量: 258.702
• InChiKey: VJXALBGDINDGFL-PELKAZGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acremine O 、 L-扁桃酸甲酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以0.2 mg的产率得到methyl (2S)-2-[[(3R,5R)-7-chloro-2,2,8-trimethyl-6,9-dioxo-1-oxaspiro[4.5]dec-7-en-3-yl]oxy]-2-phenylacetate
  参考文献：
  名称：

  Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum

  摘要：

  This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines 0 (6), P (7), Q(8), and R (9), together with the known acremines A (1), F (2), and N (3) from the fungus Acremonium persicinum cultured from the marine sponge Anomoianthella rubra. The relative configuration of acremine F (2) was determined by analyses of proton coupling constant values and NOESY data, and the absolute configuration confirmed as (IS, 4S, 6R) by X-ray crystallographic analysis of the borate ester derivative 15. Acremines O, P, and R were each shown to be of 8R configuration by H-1 NMR analyses of MPA esters. The relative configurations suggested for acremines P and Q were each deduced by molecular modeling together with NOESY and coupling constant data. The (3)J(H-C) values in acremine P were measured using the pulse sequence EXSIDE, and the observed (3)J(H8-C4) of 5.4 Hz and small (3)J(H-C) values (<1.5 Hz) from H-8 to C-10 and C-11 were fully consistent with stereoisomer 7a. For acremine Q NOESY data combined with molecular modeling established the preferred diastereomer 8a.

  DOI：

  10.1021/np4002114

文献信息

• Secondary Metabolites of the Sponge-Derived Fungus <i>Acremonium persicinum</i>
  作者：Suciati、James A. Fraser、Lynette K. Lambert、Gregory K. Pierens、Paul V. Bernhardt、Mary J. Garson

  DOI：10.1021/np4002114

  日期：2013.8.23

  This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines 0 (6), P (7), Q(8), and R (9), together with the known acremines A (1), F (2), and N (3) from the fungus Acremonium persicinum cultured from the marine sponge Anomoianthella rubra. The relative configuration of acremine F (2) was determined by analyses of proton coupling constant values and NOESY data, and the absolute configuration confirmed as (IS, 4S, 6R) by X-ray crystallographic analysis of the borate ester derivative 15. Acremines O, P, and R were each shown to be of 8R configuration by H-1 NMR analyses of MPA esters. The relative configurations suggested for acremines P and Q were each deduced by molecular modeling together with NOESY and coupling constant data. The (3)J(H-C) values in acremine P were measured using the pulse sequence EXSIDE, and the observed (3)J(H8-C4) of 5.4 Hz and small (3)J(H-C) values (<1.5 Hz) from H-8 to C-10 and C-11 were fully consistent with stereoisomer 7a. For acremine Q NOESY data combined with molecular modeling established the preferred diastereomer 8a.