N-Benzyl-N-[6-(tert-butyl-dimethyl-silanyloxy)-hex-1-ynyl]-4-methyl-benzenesulfonamide | 683246-81-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-Benzyl-N-[6-(tert-butyl-dimethyl-silanyloxy)-hex-1-ynyl]-4-methyl-benzenesulfonamide
• 英文别名: N-benzyl-N-[6-[tert-butyl(dimethyl)silyl]oxyhex-1-ynyl]-4-methylbenzenesulfonamide
• CAS: 683246-81-3
• 化学式: C₂₆H₃₇NO₃SSi
• 分子量: 471.736
• InChiKey: GNYZUNQMZHUQDE-UHFFFAOYSA-N

物化性质

• 沸点：
  549.4±60.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Benzyl-N-[6-(tert-butyl-dimethyl-silanyloxy)-hex-1-ynyl]-4-methyl-benzenesulfonamide 在 四丁基氟化铵 、 zinc trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 N-Benzyl-N-(cyclopent-1-enecarbonyl)-4-methyl-benzenesulfonamide
  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 N-Benzyl-N-[6-(tert-butyl-dimethyl-silanyloxy)-hex-1-ynyl]-4-methyl-benzenesulfonamide
  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

• Palladium-Catalyzed Regioselective Hydroarylation of Ynamides with Aryl Iodides: Easy Synthesis of Various Substituted Enamides Containing Stilbene Derivatives
  作者：Hideaki Wakamatsu、Yuichi Yoshimura、Rika Yanagisawa、Sho Kimura、Nao Osawa、Yoshihiro Natori

  DOI：10.1055/s-0036-1588874

  日期：2017.10

  Palladium-catalyzed hydroarylation of ynamides has been developed. The desired coupling products were obtained in good yields and with high regioselectivities. Various aryl iodides can be used in this reaction, permitting the syntheses of many different kinds of enamides from ynamides.

  已经开发了钯催化的炔酰胺加氢芳基化。以高产率和高区域选择性获得了所需的偶联产物。在该反应中可以使用各种芳基碘化物，允许从ynamides 合成许多不同种类的enamides。
• Synthesis of 2-Aminopyrroles Via Metal-Free Annulation of Ynamides with 2<i>H</i>-Azirines
  作者：Lianhong Jiao、Yanan Wang、Lixia Ding、Chaofeng Zhang、Xiao-Na Wang、Junbiao Chang

  DOI：10.1021/acs.joc.2c02103

  日期：2022.11.18

  A novel metal-free annulation of ynamides with 2H-azirines catalyzed by BF3·Et2O is described, leading to the construction of polysubstituted 2-aminopyrroles in a facile, flexible, and atom-economical way. This synthetic strategy proceeds with efficiency, broad substrate scope, and short reaction time under mild reaction conditions. Furthermore, the obtained annulation products could be modified to

  描述了由 BF 3 ·Et 2 O 催化的 ynamides 与 2 H-氮杂环丙烷的新型无金属环化，从而以简便、灵活且原子经济的方式构建多取代的 2-氨基吡咯。这种合成策略在温和的反应条件下具有高效、底物范围广和反应时间短的特点。此外，可以对获得的环化产物进行修改，以高产率生成多种 2-亚氨基吡咯框架。
• 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.