(+/-)-Lasiodiplodin | 65716-53-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (+/-)-Lasiodiplodin
• 英文别名: 2-Hydroxy-4-methoxy-7-methyl-7,8,9,10,11,12,13,14-octahydro-6-oxabenzocyclododecen-5-one；14-hydroxy-16-methoxy-4-methyl-3-oxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-2-one
• CAS: 65716-53-2
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: OKWRDLQBKAOJNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-Lasiodiplodin 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 以9.8 mg的产率得到1,3-Dibromo-2-hydroxy-4-methoxy-7-methyl-7,8,9,10,11,12,13,14-octahydro-6-oxa-benzocyclododecen-5-one
  参考文献：
  名称：

  Lactones from a brown alga endophytic fungus (No. ZZF36) from the South China Sea and their antimicrobial activities

  摘要：

  Two new metabolites named 6-oxo-de-O-methyllasiodiplodin (1) and (E)-9-etheno-lasiodiplodin (2), with three known compounds lasiodiplodin (3), de-O-methyllasiodiplodin (4), and 5-hydroxy-de-O-methyllasiodiplodin (5), were isolated from the mycelium extracts of a brown alga endophytic fungus (No. ZZF36) obtained from the South China Sea. Their structures were elucidated using spectroscopic methods, mainly 1D and 2D NMR. Additionally, the structure of compound 1 was confirmed by single crystal X-ray diffraction analysis. The antimicrobial activities of lasiodiplodins, and the 13-acetyl and 12,14-dibromo derivatives of lasiodiplodin were tested for the first time and the results were compared to each other. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.081
• 作为产物：
  描述：

  (+/-)-Dodeca-2,3-dien-11-olid 在 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.25h， 生成 (+/-)-Lasiodiplodin
  参考文献：
  名称：

  2，3-Alkadiensäureesterals Dienophile; 合成（+）-（R）-Lasiodiplodin合成反应

  摘要：

  2,3-链烷二酸作为亲二烯体，在（+）-（R）-Lasiodiplodin合成中的应用

  DOI：

  10.1002/hlca.19820650827

文献信息

• 2, 3-Alkadiensäureester als Dienophile; Anwendung bei der Synthese von (+)-(<i>R</i>)-Lasiodiplodin
  作者：Margot Fink、Hans Gaier、Hans Gerlacho

  DOI：10.1002/hlca.19820650827

  日期：1982.12.15

  2,3-Alkadienoates as Dienophiles, Application in the Synthesis of (+)-(R)-Lasiodiplodin

  2,3-链烷二酸作为亲二烯体，在（+）-（R）-Lasiodiplodin合成中的应用
• Lactones from a brown alga endophytic fungus (No. ZZF36) from the South China Sea and their antimicrobial activities
  作者：Rui-yun Yang、Chun-yuan Li、Yong-cheng Lin、Guang-tian Peng、Zhi-gang She、Shi-ning Zhou

  DOI：10.1016/j.bmcl.2006.05.081

  日期：2006.8

  Two new metabolites named 6-oxo-de-O-methyllasiodiplodin (1) and (E)-9-etheno-lasiodiplodin (2), with three known compounds lasiodiplodin (3), de-O-methyllasiodiplodin (4), and 5-hydroxy-de-O-methyllasiodiplodin (5), were isolated from the mycelium extracts of a brown alga endophytic fungus (No. ZZF36) obtained from the South China Sea. Their structures were elucidated using spectroscopic methods, mainly 1D and 2D NMR. Additionally, the structure of compound 1 was confirmed by single crystal X-ray diffraction analysis. The antimicrobial activities of lasiodiplodins, and the 13-acetyl and 12,14-dibromo derivatives of lasiodiplodin were tested for the first time and the results were compared to each other. (c) 2006 Elsevier Ltd. All rights reserved.