tert-butyl 5-oxooctadecylcarbamate | 1333316-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl 5-oxooctadecylcarbamate
• CAS: 1333316-67-8
• 化学式: C₂₃H₄₅NO₃
• 分子量: 383.615
• InChiKey: CCHBAODSNMWTTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  27.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-oxooctadecylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以62 mg的产率得到6-tridecyl-2,3,4,5-tetrahydropyridine
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Natural Product-Based 6-Alkyl-2,3,4,5-tetrahydropyridines

  摘要：

  Seven 6-alkyl-2,3,4,5-tetrahydropyridines (5a-5g) that mimic the natural piperideines that were recently identified in fire ant venom have been synthesized. Compounds 5c-5g with C-6 alkyl chain lengths from C14 to C18 showed varying degrees of antifungal activities, with 5e (6-hexadecyl-2,3,4,5-tetrahydropyridine) and 5f (6-heptadecyl-2,3,4,5-tetrahydropyridine) being the most active. Compound Se exhibited minimum fungicidal concentrations of 3.8, 15.0, 7.5, and 7.5 mu g/mL against Cryptococcus neoformans, Candida albicans, Candida glabrata, and Candida krusei, respectively. The antifungal activities of these compounds appear to be associated with the C-6 side chain length. This study represents the first effort to evaluate antifungal activities of synthetic analogues of the newly identified fire ant venom alkaloids.

  DOI：

  10.1021/np200644s
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 、 1-十三烷基溴化镁 在 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 tert-butyl 5-oxooctadecylcarbamate
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Natural Product-Based 6-Alkyl-2,3,4,5-tetrahydropyridines

  摘要：

  Seven 6-alkyl-2,3,4,5-tetrahydropyridines (5a-5g) that mimic the natural piperideines that were recently identified in fire ant venom have been synthesized. Compounds 5c-5g with C-6 alkyl chain lengths from C14 to C18 showed varying degrees of antifungal activities, with 5e (6-hexadecyl-2,3,4,5-tetrahydropyridine) and 5f (6-heptadecyl-2,3,4,5-tetrahydropyridine) being the most active. Compound Se exhibited minimum fungicidal concentrations of 3.8, 15.0, 7.5, and 7.5 mu g/mL against Cryptococcus neoformans, Candida albicans, Candida glabrata, and Candida krusei, respectively. The antifungal activities of these compounds appear to be associated with the C-6 side chain length. This study represents the first effort to evaluate antifungal activities of synthetic analogues of the newly identified fire ant venom alkaloids.

  DOI：

  10.1021/np200644s

文献信息

• Synthesis and Antifungal Activity of Natural Product-Based 6-Alkyl-2,3,4,5-tetrahydropyridines
  作者：Liyan Dai、Melissa R. Jacob、Shabana I. Khan、Ikhlas A. Khan、Alice M. Clark、Xing-Cong Li

  DOI：10.1021/np200644s

  日期：2011.9.23

  Seven 6-alkyl-2,3,4,5-tetrahydropyridines (5a-5g) that mimic the natural piperideines that were recently identified in fire ant venom have been synthesized. Compounds 5c-5g with C-6 alkyl chain lengths from C14 to C18 showed varying degrees of antifungal activities, with 5e (6-hexadecyl-2,3,4,5-tetrahydropyridine) and 5f (6-heptadecyl-2,3,4,5-tetrahydropyridine) being the most active. Compound Se exhibited minimum fungicidal concentrations of 3.8, 15.0, 7.5, and 7.5 mu g/mL against Cryptococcus neoformans, Candida albicans, Candida glabrata, and Candida krusei, respectively. The antifungal activities of these compounds appear to be associated with the C-6 side chain length. This study represents the first effort to evaluate antifungal activities of synthetic analogues of the newly identified fire ant venom alkaloids.