N-(3-bromoprop-2-ynyl)-4-methyl-N-prop-2-enylbenzenesulfonamide | 874894-25-4

• 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-(3-bromoprop-2-ynyl)-4-methyl-N-prop-2-enylbenzenesulfonamide
• CAS: 874894-25-4
• 化学式: C₁₃H₁₄BrNO₂S
• 分子量: 328.23
• InChiKey: XOZZBEIQCXSVLH-UHFFFAOYSA-N

物化性质

• 沸点：
  419.6±55.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(3-bromoprop-2-ynyl)-4-methyl-N-prop-2-enylbenzenesulfonamide 在 copper(l) iodide 、 偶氮二甲酸二异丙酯 、 盐酸羟胺 、 正丁胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-methyl-N-[6-[6-[(4-methylphenyl)sulfonyl-prop-2-ynylamino]hexa-2,4-diynoxy]hexa-2,4-diynyl]-N-prop-2-enylbenzenesulfonamide
  参考文献：
  名称：

  Metathesis and Metallotropy:  A Versatile Combination for the Synthesis of Oligoenynes

  摘要：

  We have demonstrated that the combined use of enyne metathesis and metallotropic [1,3]-shift of the corresponding alkynyl ruthenium carbenes is a powerful synthetic tool to construct oligoenynes. In this reaction, alkynyl carbene intermediates formed from an initial ring-closing metathesis reaction (RCM) undergo repetitive [1,3]-shifts and RCMs to give the final products. Linear poly-1,3-diynes containing repeating functionality of the type -[XCH2CCCCCH2]n- generated long-chain conjugated oligoenynes up to n = 5.

  DOI：

  10.1021/ja057153c
• 作为产物：
  描述：

  N-tosyl-N-allylpropargylamine 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以90%的产率得到N-(3-bromoprop-2-ynyl)-4-methyl-N-prop-2-enylbenzenesulfonamide
  参考文献：
  名称：

  Yun, Sang Young; Kim, Mansuk; Lee, Daesung, Journal of the American Chemical Society, 2009, vol. 131, p. 24 - 25

  摘要：

  DOI：

文献信息

• A stereoselective intramolecular cyclopropanation via a de novo class of push–pull carbenes derived from DMDO-epoxidations of chiral ynamides
  作者：Hongyan Li、Jennifer E. Antoline、Jin-Haek Yang、Ziyad F. Al-Rashid、Richard P. Hsung

  DOI：10.1039/c0nj00063a

  日期：——

  This work describes the first examples of diastereoselective intramolecular cyclopropanations of a de novo class of push–pull carbenes derived from DMDO-epoxidations of chiral ynamides. This reaction sequence essentially constitutes a tandem epoxidation–cyclopropanation that effectively gives rise to a series of structurally unique amido-cyclopropanes. A plausible mechanistic model is proposed revealing insights into this novel cyclopropanation process.

  这项研究首次举例说明了从手性炔酰胺的 DMDO 环氧化反应中衍生出的一类新的推拉碳烯的非对映选择性分子内环丙烷化反应。这一反应序列基本上构成了串联环氧化-环丙烷化反应，有效地生成了一系列结构独特的氨基环丙烷。研究人员提出了一个合理的机理模型，揭示了这一新型环丙烷化过程的奥秘。
• Structure and Reactivity of Alkyne-Chelated Ruthenium Alkylidene Complexes
  作者：Kung-Pern Wang、Sang Young Yun、Daesung Lee、Donald J. Wink

  DOI：10.1021/ja907155r

  日期：2009.10.28

  The isolation and structural characterization of alkyne-bound Ru alkylidene complexes has been elusive. However, a sequential enyne ring-closing metathesis of a diyne moiety and metallotropic [1,3]-shift followed by a second enyne ring-closing metathesis allowed the formation of a highly stable alkyne-chelated ruthenium complex. The full characterization of this complex was realized by NMR spectroscopy and X-ray crystallography.
• Reactivity and Selectivity of 1,3-Diyn-6-enes in Electrophilic Transition Metal-Catalyzed Reactions
  作者：Eun Jin Cho、Mansuk Kim、Daesung Lee

  DOI：10.1021/ol062335c

  日期：2006.11.9

  [GRAPHICS]1,3-Diyne is an excellent source of alkynyl metal carbene species upon activation with an electrophilic metal catalyst. The products from this bond reorganization process suggest that the metal carbene species, generated from the preferential participation of an acetate over an alkene in the first step, undergo an efficient metallotropic [1,3]-shift followed by termination via cyclopropanation.