3,5-dioxo-dodec-10-ynoic acid tert-butyl ester | 618105-64-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3,5-dioxo-dodec-10-ynoic acid tert-butyl ester
• 英文别名: Tert-butyl 3,5-dioxododec-10-ynoate
• CAS: 618105-64-9
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: WOZZXTJCFIQWIP-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±27.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dioxo-dodec-10-ynoic acid tert-butyl ester 在 (tBuO)3W<*>CCMe3 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.83h， 生成 2,19-dioxa-bicyclo[16.3.1]docosa-1⁽²¹⁾,18⁽²²⁾-dien-12-yn-20-one
  参考文献：
  名称：

  Study towards bioactive pyrone derivatives from the marine red alga Phacelocarpus labillardieri

  摘要：

  Red algae of the genus Phacelocarpus labillardieri produce a structurally rather unique class of macrocyclic pyrone derivatives with phospholipase A, inhibiting properties and potential neuromuscular blocking activity. They were also shown to be potent feeding inhibitors for various marine herbivorous gastropods. Described herein is the first preparative study towards these conspicuous secondary metabolites. Their carbon skeleton has been assembled in a few straightforward steps using ring closing alkyne metathesis (RCAM) catalyzed by the Schrock alkylidyne complex (tBuO)(3)WdropCCMe(3) to forge the meta-cyclophane core with high efficiency. (C) 2003 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)00815-9
• 作为产物：
  描述：

  oct-6-ynoic acid 在 四甲基乙二胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 正戊烷 为溶剂， 反应 6.75h， 生成 3,5-dioxo-dodec-10-ynoic acid tert-butyl ester
  参考文献：
  名称：

  Study towards bioactive pyrone derivatives from the marine red alga Phacelocarpus labillardieri

  摘要：

  Red algae of the genus Phacelocarpus labillardieri produce a structurally rather unique class of macrocyclic pyrone derivatives with phospholipase A, inhibiting properties and potential neuromuscular blocking activity. They were also shown to be potent feeding inhibitors for various marine herbivorous gastropods. Described herein is the first preparative study towards these conspicuous secondary metabolites. Their carbon skeleton has been assembled in a few straightforward steps using ring closing alkyne metathesis (RCAM) catalyzed by the Schrock alkylidyne complex (tBuO)(3)WdropCCMe(3) to forge the meta-cyclophane core with high efficiency. (C) 2003 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)00815-9