(1R,4S)-2-[6-[tert-butyl(dimethyl)silyl]oxyhex-1-ynyl]-1,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one | 683246-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1R,4S)-2-[6-[tert-butyl(dimethyl)silyl]oxyhex-1-ynyl]-1,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 683246-69-7
• 化学式: C₂₁H₃₇NO₂Si
• 分子量: 363.616
• InChiKey: PILKJCQAGVNGDK-DYESRHJHSA-N

物化性质

• 沸点：
  403.4±47.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,4S)-2-[6-[tert-butyl(dimethyl)silyl]oxyhex-1-ynyl]-1,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 6-((1R,4S)-1,7,7-Trimethyl-3-oxo-2-aza-bicyclo[2.2.1]hept-2-yl)-hex-5-ynal
  参考文献：
  名称：

  A Ring-Closing Yne-Carbonyl Metathesis of Ynamides

  摘要：

  An acid-catalyzed ring-closing ynamide-carbonyl metathesis is described here. This hetero RCM methodology is applicable to the construction of carbocycles as well as heterocycles such as chromenes, quinolizidines, indolizidines, and pyrrolizidines.

  DOI：

  10.1021/ol052487s
• 作为产物：
  描述：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 potassium phosphate 、 正丁基锂 、 1,10-菲罗啉 、 copper (II) sulfite 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 5.75h， 生成 (1R,4S)-2-[6-[tert-butyl(dimethyl)silyl]oxyhex-1-ynyl]-1,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Copper Sulfate-Pentahydrate-1,10-Phenanthroline Catalyzed Amidations of Alkynyl Bromides. Synthesis of Heteroaromatic Amine Substituted Ynamides

  摘要：

  A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO(4)(.)5H(2)O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.

  DOI：

  10.1021/ol049827e

文献信息

• Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and <i>Z</i>-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides
  作者：Xuejun Zhang、Yanshi Zhang、Jian Huang、Richard P. Hsung、Kimberly C. M. Kurtz、Jossian Oppenheimer、Matthew E. Petersen、Irina K. Sagamanova、Lichun Shen、Michael R. Tracey

  DOI：10.1021/jo060230h

  日期：2006.5.1

  method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C−N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry

  在此描述了用于将各种酰胺与炔基溴化物偶联的通用且有效的方法。这种新颖的酰胺化反应涉及使用五水合硫酸铜（II）和1,10-菲咯啉来指导sp-C-N键形成的催化方案，从而通过分子内酰胺化形成结构上多样的酰胺，包括大环酰胺。鉴于对酰胺化学的浓厚兴趣，这种原子经济的酰胺合成方法应引起有机合成界的进一步关注。
• Copper Sulfate-Pentahydrate-1,10-Phenanthroline Catalyzed Amidations of Alkynyl Bromides. Synthesis of Heteroaromatic Amine Substituted Ynamides
  作者：Yanshi Zhang、Richard P. Hsung、Michael R. Tracey、Kimberly C. M. Kurtz、Eymi L. Vera

  DOI：10.1021/ol049827e

  日期：2004.4.1

  A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO(4)(.)5H(2)O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.
• A Ring-Closing Yne-Carbonyl Metathesis of Ynamides
  作者：Kimberly C. M. Kurtz、Richard P. Hsung、Yanshi Zhang

  DOI：10.1021/ol052487s

  日期：2006.1.1

  An acid-catalyzed ring-closing ynamide-carbonyl metathesis is described here. This hetero RCM methodology is applicable to the construction of carbocycles as well as heterocycles such as chromenes, quinolizidines, indolizidines, and pyrrolizidines.