(1S,2S,4R,6R,8S,12R,14R)-14-hydroxy-6-methoxy-4-methyl-8-propyl-3,9,16-trioxatricyclo[10.3.1.0(2,4)]hexadecan-10-one | 1237526-74-7

• 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: (1S,2S,4R,6R,8S,12R,14R)-14-hydroxy-6-methoxy-4-methyl-8-propyl-3,9,16-trioxatricyclo[10.3.1.0(2,4)]hexadecan-10-one
• CAS: 1237526-74-7
• 化学式: C₁₈H₃₀O₆
• 分子量: 342.433
• InChiKey: UTZLEFAILUOSLB-IQSREBOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  77.52
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-[2-[3-(Methoxycarbonylamino)prop-1-enyl]-1,3-oxazol-4-yl]pent-2-enoic acid 、 (1S,2S,4R,6R,8S,12R,14R)-14-hydroxy-6-methoxy-4-methyl-8-propyl-3,9,16-trioxatricyclo[10.3.1.0(2,4)]hexadecan-10-one 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 0.17h， 以66%的产率得到
  参考文献：
  名称：

  Total synthesis of neopeltolide and analogs

  摘要：

  Neopeltolide, a potent cytotoxin from a Carribean sponge, was synthesized through a brief sequence that highlights the use of ethers as oxocarbenium ion precursors. Other key steps include an acid-mediated etherification and sequence that features a Sonogashira reaction, an intramolecular alkyne hydrosilylation reaction, and a Tamao oxidation. The alkene that is required for the oxidative cyclization can be hydrogenated to provide access to the natural product or an epimer, or can be epoxiclized or dihydroxylated to form polar analogs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.066
• 作为产物：
  描述：

  (1R,5S,7S,11S,13R,Z)-13-hydroxy-7-methoxy-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadec-9-en-3-one 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到(1S,2S,4R,6R,8S,12R,14R)-14-hydroxy-6-methoxy-4-methyl-8-propyl-3,9,16-trioxatricyclo[10.3.1.0(2,4)]hexadecan-10-one
  参考文献：
  名称：

  Total synthesis of neopeltolide and analogs

  摘要：

  Neopeltolide, a potent cytotoxin from a Carribean sponge, was synthesized through a brief sequence that highlights the use of ethers as oxocarbenium ion precursors. Other key steps include an acid-mediated etherification and sequence that features a Sonogashira reaction, an intramolecular alkyne hydrosilylation reaction, and a Tamao oxidation. The alkene that is required for the oxidative cyclization can be hydrogenated to provide access to the natural product or an epimer, or can be epoxiclized or dihydroxylated to form polar analogs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.066