3-((3E,7E,11E)-4,8,12,16-tetramethyl-6-(phenylsulfonyl)heptadeca-3,7,11,15-tetraen-1-yl)tetrahydrofuran | 1331771-42-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-((3E,7E,11E)-4,8,12,16-tetramethyl-6-(phenylsulfonyl)heptadeca-3,7,11,15-tetraen-1-yl)tetrahydrofuran
• CAS: 1331771-42-6
• 化学式: C₃₁H₄₆O₃S
• 分子量: 498.77
• InChiKey: MZUPDLQPMXVSPZ-XIDYRHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-((3E,7E,11E)-4,8,12,16-tetramethyl-6-(phenylsulfonyl)heptadeca-3,7,11,15-tetraen-1-yl)tetrahydrofuran 在 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以75%的产率得到3-[(3E,7E,11E)-4,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl]tetrahydrofuran
  参考文献：
  名称：

  Concise synthesis and structure–activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge

  摘要：

  Structure activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.009
• 作为产物：
  描述：

  3-(四氢呋喃-3-基)丙酸乙酯 在 四溴化碳 、 potassium tert-butylate 、 二异丁基氢化铝 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.83h， 生成 3-((3E,7E,11E)-4,8,12,16-tetramethyl-6-(phenylsulfonyl)heptadeca-3,7,11,15-tetraen-1-yl)tetrahydrofuran
  参考文献：
  名称：

  Concise synthesis and structure–activity relationship of furospinosulin-1, a hypoxia-selective growth inhibitor from marine sponge

  摘要：

  Structure activity relationship of furospinosulin-1 (1), a hypoxia-selective growth inhibitor isolated from marine sponge, was investigated. Concise synthetic method of 1 was developed, and some structurally modified analogues were prepared. Biological evaluation of them revealed that the whole chemical structure was important for the hypoxia-selective growth inhibitory activity of 1. Among prepared, the desmethyl analogue 30 showed excellent hypoxia-selective inhibitory activity similar to that of 1 and also exhibited in vivo anti-tumor activity with oral administration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.009