(1R,5S,7S,9Z,11S)-7-methoxy-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadec-9-ene-3,13-dione | 1176813-61-8

• 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,9Z,11S)-7-methoxy-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadec-9-ene-3,13-dione
• CAS: 1176813-61-8
• 化学式: C₁₈H₂₈O₅
• 分子量: 324.417
• InChiKey: MUMGVSKNNJNDFQ-GQEFBNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以74%的产率得到(1R,5S,7S,9S,11R)-7-methoxy-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadecane-3,13-dione
  参考文献：
  名称：

  Tu, Wangyang; Floreancig, Paul E., Angewandte Chemie - International Edition, 2009, vol. 48, p. 4567 - 4571

  摘要：

  DOI：
• 作为产物：
  描述：

  (4R,10S,12S,Z)-10-methoxy-8-methyl-4-(prop-2-yn-1-yl)-12-propyl-1,5-dioxacyclododec-7-en-2-one 在 1-癸炔 、 [RhCl2(p-cymene)]2 、 三(2-呋喃基)膦 、 sodium carbonate 、 溶剂黄146 、 2,6-二氯吡啶 、 lithium perchlorate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 、 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 (1R,5S,7S,9Z,11S)-7-methoxy-9-methyl-5-propyl-4,15-dioxabicyclo[9.3.1]pentadec-9-ene-3,13-dione
  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

• Tu, Wangyang; Floreancig, Paul E., Angewandte Chemie - International Edition, 2009, vol. 48, p. 4567 - 4571
  作者：Tu, Wangyang、Floreancig, Paul E.

  DOI：——

  日期：——
• Total synthesis of neopeltolide and analogs
  作者：Yubo Cui、Wangyang Tu、Paul E. Floreancig

  DOI：10.1016/j.tet.2010.03.066

  日期：2010.6

  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.