(1S,8R,11R,13R)-17-Bromo-8-methyl-9,14-dioxa-tricyclo[11.2.2.0^1,11]heptadec-16-en-2-yne-10,15-dione | 907157-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1S,8R,11R,13R)-17-Bromo-8-methyl-9,14-dioxa-tricyclo[11.2.2.0^1,11]heptadec-16-en-2-yne-10,15-dione
• 英文别名: (1S,8R,11R,13R)-17-bromo-8-methyl-9,14-dioxatricyclo[11.2.2.01,11]heptadec-16-en-2-yne-10,15-dione
• CAS: 907157-57-7
• 化学式: C₁₆H₁₇BrO₄
• 分子量: 353.213
• InChiKey: WNJPHDSVLMQSGE-DDFXLWFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,8R,11R,13R)-17-Bromo-8-methyl-9,14-dioxa-tricyclo[11.2.2.0^1,11]heptadec-16-en-2-yne-10,15-dione 在 4-二甲氨基吡啶 、 N,N-dicyclohexylurea 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones

  摘要：

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.

  DOI：

  10.1021/ol061198g
• 作为产物：
  描述：

  (R)-oct-4-yn-2-ol 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 potassium hydride 、 1,3-丙二胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.5h， 生成 (1S,8R,11R,13R)-17-Bromo-8-methyl-9,14-dioxa-tricyclo[11.2.2.0^1,11]heptadec-16-en-2-yne-10,15-dione
  参考文献：
  名称：

  Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones

  摘要：

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.

  DOI：

  10.1021/ol061198g

文献信息

• Highly Diastereoselective Type-I IMDA Reaction Forming Medium-Sized Macrolactones
  作者：Jeong-Taek Shin、Sung-Cho Hong、Seunghoon Shin、Cheon-Gyu Cho

  DOI：10.1021/ol061198g

  日期：2006.7.1

  Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.