(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 | 1228293-84-2

• 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: (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
• CAS: 1228293-84-2
• 化学式: C₁₈H₃₀O₅
• 分子量: 326.433
• InChiKey: JCKIFCSTJBOVIR-QQUFLGISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (1R,5S,7S,9Z,11S)-7-methoxy-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadec-9-ene-3,13-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以84%的产率得到(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
  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

文献信息

• Synthesis and Biological Evaluation of Neopeltolide and Analogs
  作者：Yubo Cui、Raghavan Balachandran、Billy W. Day、Paul E. Floreancig

  DOI：10.1021/jo2023685

  日期：2012.3.2

  The synthesis of neopeltolide analogues that contain variations in the oxazole-containing side chain and in the macrolide core are reported along with the GI(50) values for these compounds against MCF-7, HCT-116, and p53 knockout HCT-116 cell lines. Although biological activity is sensitive to changes in the macrocycle and the side chain, several analogues displayed GI(50) values of <25 nM. Neopeltolide and several of the more potent analogues were significantly less potent against p53 knockout cells, suggesting that p53 plays an auxiliary role in the activity of these compounds.