5-[(Z)-dodec-5-enoyl]-2,2-dimethyl-1,3-dioxane-4,6-dione | 1026681-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(Z)-dodec-5-enoyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1026681-96-8
• 化学式: C₁₈H₂₈O₅
• 分子量: 324.417
• InChiKey: GACNKFAFDMFJRU-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(Z)-dodec-5-enoyl]-2,2-dimethyl-1,3-dioxane-4,6-dione 、 高丝氨酸内酯氢溴酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以99%的产率得到(S)-3-oxo-(7Z)-tetradecenoyl-homoserine lactone
  参考文献：
  名称：

  Long-Chain Acyl-Homoserine Lactones from Methylobacterium mesophilicum: Synthesis and Absolute Configuration

  摘要：

  The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.

  DOI：

  10.1021/np900043j
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 顺-5-十二碳烯酸 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， 反应 24.0h， 生成 5-[(Z)-dodec-5-enoyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Long-Chain Acyl-Homoserine Lactones from Methylobacterium mesophilicum: Synthesis and Absolute Configuration

  摘要：

  The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.

  DOI：

  10.1021/np900043j

文献信息

• Long-Chain Acyl-Homoserine Lactones from <i>Methylobacterium mesophilicum:</i> Synthesis and Absolute Configuration
  作者：Armando M. Pomini、Pedro L. R. Cruz、Cláudia Gai、Welington L. Araújo、Anita J. Marsaioli

  DOI：10.1021/np900043j

  日期：2009.12.28

  The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.