acremine C

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: acremine C
• 英文别名: 2,2,7-Trimethylchromen-6-ol
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: RIIOGEMWMHCDHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acremine C 、 乙酸酐 在 吡啶 作用下， 生成 Acetic acid 2,2,7-trimethyl-2H-chromen-6-yl ester
  参考文献：
  名称：

  Acremines A–F, novel secondary metabolites produced by a strain of an endophytic Acremonium, isolated from sporangiophores of Plasmopara viticola in grapevine leaves

  摘要：

  Six novel metabolites, acremines A-F have been isolated from agar cultures of a strain of Acremonium sp. Their structures and stereochemistry were elucidated using a combination of 13 C and H-1 homo and heteronuclear 2D NMR experiments and X-ray analysis. Acremines A-D inhibited the germination of sporangia of Plasmopara viticola. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.094
• 作为产物：
  描述：

  2-methyl-5-[(1E)-3-methylbuta-1,3-dienyl]benzene-1,4-diol 生成 acremine C
  参考文献：
  名称：

  通过高度区域选择性和立体选择性Diels-Alder反应仿生合成二聚体代谢产物Acremine G

  摘要：

  合成的二聚体代谢产物顶峰G的特征在于TBS保护的对苯二酚二烯与结构相关的烯基醌之间具有高度区域选择性和立体选择性Diels-Alder反应。在脱保护条件（原位生成的HF）下，大气中的主要内含物[4 + 2]加合物缓慢转化为丙烯酰胺G。

  DOI：

  10.1021/ol901004e

文献信息

• Biomimetic Synthesis of Dimeric Metabolite Acremine G via a Highly Regioselective and Stereoselective Diels−Alder Reaction
  作者：Elias Arkoudis、Ioannis N. Lykakis、Charis Gryparis、Manolis Stratakis

  DOI：10.1021/ol901004e

  日期：2009.7.16

  The dimeric metabolite acremine G was synthesized featuring a highly regioselective and stereoselective Diels−Alder reaction between a TBS-protected hydroquinone diene and a structurally related alkenyl quinone. The major endo [4 + 2] adduct slowly transforms to acremine G by the atmospheric air under the deprotection conditions (in situ generated HF).

  合成的二聚体代谢产物顶峰G的特征在于TBS保护的对苯二酚二烯与结构相关的烯基醌之间具有高度区域选择性和立体选择性Diels-Alder反应。在脱保护条件（原位生成的HF）下，大气中的主要内含物[4 + 2]加合物缓慢转化为丙烯酰胺G。
• Acremines A–F, novel secondary metabolites produced by a strain of an endophytic Acremonium, isolated from sporangiophores of Plasmopara viticola in grapevine leaves
  作者：Gemma Assante、Sabrina Dallavalle、Luciana Malpezzi、Gianluca Nasini、Santella Burruano、Livio Torta

  DOI：10.1016/j.tet.2005.05.094

  日期：2005.8

  Six novel metabolites, acremines A-F have been isolated from agar cultures of a strain of Acremonium sp. Their structures and stereochemistry were elucidated using a combination of 13 C and H-1 homo and heteronuclear 2D NMR experiments and X-ray analysis. Acremines A-D inhibited the germination of sporangia of Plasmopara viticola. (c) 2005 Elsevier Ltd. All rights reserved.