N-but-2-ynyl-N-cyclohex-2-enyl-4-methyl-benzenesulfonamide

• 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-but-2-ynyl-N-cyclohex-2-enyl-4-methyl-benzenesulfonamide
• 英文别名: N-but-2-ynyl-N-cyclohex-2-en-1-yl-4-methylbenzenesulfonamide
• 化学式: C₁₇H₂₁NO₂S
• 分子量: 303.425
• InChiKey: CPLGVCRHLASILQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-but-2-ynyl-N-cyclohex-2-enyl-4-methyl-benzenesulfonamide 在 Pd₃⁽⁴⁺⁾*F₆Sb^(1-)*3CH₃S^(1-)*3C₁₈H₁₅P 、 苯甲酸 作用下， 以 甲苯 为溶剂， 以66%的产率得到3-ethylidene-1-tosyl-2,3,3a,6,7,7a-hexahydro-1H-indole
  参考文献：
  名称：

  1,6-烯炔与全金属芳族三核配合物和羧酸的互补反应性

  摘要：

  作为《五十周年综合报告》的一部分发行-金色周年纪念日 抽象的 呈现了在由羧酸活化的三核金属络合物存在下1，6-烯炔的不同反应性。雷公藤甲素催化剂能够使底物环化，并随后将亲核试剂掺入最终产物中。相反，在相应条件下，在相应的三铝配合物的存在下，顺序环化/双键移位发生在类似条件下。 呈现了在由羧酸活化的三核金属络合物存在下1，6-烯炔的不同反应性。雷公藤甲素催化剂能够使底物环化，并随后将亲核试剂掺入最终产物中。相反，在相应条件下，在相应的三铝配合物的存在下，顺序环化/双键移位发生在类似条件下。

  DOI：

  10.1055/s-0037-1611653
• 作为产物：
  描述：

  3-溴环己烯 、 4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 以99%的产率得到N-but-2-ynyl-N-cyclohex-2-enyl-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  ROM-RCM of cycloalkene-yne

  摘要：

  Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of cycloalkene-yne was demonstrated using a first- or second-generation ruthenium complex. When cycloalkenes bearing the alkyne part at the C-3 position were reacted with a first-generation ruthenium-carbene complex under an atmosphere of ethylene, ROM-RCM proceeded smoothly to give skeletal reorganized products in good yields. In this reaction, cycloalkene-ynes having terminal alkyne were suitable. On the other hand, when cycloalkenes bearing the alkyne part at the C-1 position were treated with a second-generation ruthenium-carbene complex, ROM-RCM proceeded smoothly to give bicyclic compounds and/or dimeric compounds in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.030

文献信息

• Versatile Tandem Ring-Opening/Ring-Closing Metathesis Polymerization: Strategies for Successful Polymerization of Challenging Monomers and Their Mechanistic Studies
  作者：Hyeon Park、Eun-Hye Kang、Laura Müller、Tae-Lim Choi

  DOI：10.1021/jacs.5b12223

  日期：2016.2.24

  electronic effects of the alkyne substituents influenced alkyne addition selectivity and the polymerization reactivity. Further polymerization kinetics studies revealed that the rate-determining step of monomers containing certain internal alkynes was the six-membered cyclization step via β-addition, whereas that for other monomers was the conventional intermolecular propagation step, as observed in other

  串联开环/闭环复分解 (RO/RCM) 导致极快的活性聚合；然而，根据之前的报道，只有含有某些环烯烃、末端炔烃和氮连接体组合的单体才能成功地进行串联聚合。在检查了聚合途径后，我们提出相对缓慢的分子内环化可能会导致竞争性副反应，例如分子间交叉复分解反应，以形成无活性的传播物种。因此，我们开发了两种策略来提高串联聚合效率。首先，我们修改了单体结构，通过增强 Thorpe-Ingold 效应来加速串联 RO/RCM 环化。该策略提高了聚合速率并抑制了链转移反应以实现受控聚合，甚至对于树枝状聚合物的具有挑战性的合成。或者，降低反应浓度有利于串联聚合，这表明缓慢的串联 RO/RCM 环化步骤是之前失败的主要原因。为了拓宽单体范围，我们使用含有内部炔烃的单体，并观察到由于内部炔烃上的非选择性 α-加成和 β-加成，产生了具有不同环尺寸的两种不同聚合物单元。对具有内部炔烃的各种单体进行的彻底实验表明，炔
• Ruthenium-Catalyzed Ring-Opening and Ring-Closing Enyne Metathesis
  作者：Tsuyoshi Kitamura、Miwako Mori

  DOI：10.1021/ol015606m

  日期：2001.4.1

  a CH2Cl2 solution of an enyne containing the cycloalkene moiety was stirred in the presence of ruthenium-carbene complex (10 mol %) at room temperature under ethylene gas (1 atm), ring-opening and ring-closing metathesis occurred to afford cyclized triene. The reaction was carried out under argon gas, and no cyclized product was obtained. Enynes with a terminal alkyne gave good results.

  [反应：请参见文字]。当在室温下在乙烯气体（1个大气压）下于钌-卡宾配合物（10摩尔％）存在下搅拌含有环烯烃部分的烯炔的CH2Cl2溶液时，发生开环和闭环复分解反应，得到环化的三烯。该反应在氩气下进行，未获得环化产物。炔烃与末端炔烃的合成效果良好。
• Coupling/cyclization of 1,6-enynes with aryl halides: an efficient and general route for the synthesis of functionalized hexahydroindole and hexahydrobenzofuran derivatives
  作者：Tuan-jie Meng、Yi-min Hu、Yong-jie Sun、Tao Zhu、Shaowu Wang

  DOI：10.1016/j.tet.2010.09.029

  日期：2010.11

  An efficient and general route for the synthesis of functionalized hexahydroindole and hexahydrobenzofuran derivatives has been developed via the palladium-catalyzed domino coupling/cyclization reaction of 1,6-enynes and aryl halides. The results indicated that the electronic properties of the aryl halides strongly affect the reaction yields.

  通过钯催化的1,6-炔烃和芳基卤化物的多米诺偶联/环化反应，已经开发出一种有效的通用途径，用于合成官能化的六氢吲哚和六氢苯并呋喃衍生物。结果表明，芳基卤化物的电子性质强烈影响反应产率。
• Complementary Reactivity of 1,6-Enynes with All-Metal Aromatic Trinuclear Complexes and Carboxylic Acids
  作者：Chiara Cecchini、Matteo Lanzi、Gianpiero Cera、Max Malacria、Giovanni Maestri

  DOI：10.1055/s-0037-1611653

  日期：2019.3

  the presence of a trinuclear metal complex activated by a carboxylic acid is presented. The triplatinum catalyst enables the cyclization of the substrate and subsequent incorporation of a nucleophile in the final product. In contrast, sequential cyclization/double bond shift occurs under analogous conditions in the presence of the corresponding tripalladium complex. The distinct reactivity of 1,6-enynes

  作为《五十周年综合报告》的一部分发行-金色周年纪念日 抽象的 呈现了在由羧酸活化的三核金属络合物存在下1，6-烯炔的不同反应性。雷公藤甲素催化剂能够使底物环化，并随后将亲核试剂掺入最终产物中。相反，在相应条件下，在相应的三铝配合物的存在下，顺序环化/双键移位发生在类似条件下。 呈现了在由羧酸活化的三核金属络合物存在下1，6-烯炔的不同反应性。雷公藤甲素催化剂能够使底物环化，并随后将亲核试剂掺入最终产物中。相反，在相应条件下，在相应的三铝配合物的存在下，顺序环化/双键移位发生在类似条件下。
• ROM-RCM of cycloalkene-yne
  作者：Tsuyoshi Kitamura、Yuichi Kuzuba、Yoshihiro Sato、Hideaki Wakamatsu、Reiko Fujita、Miwako Mori

  DOI：10.1016/j.tet.2004.05.030

  日期：2004.8

  Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of cycloalkene-yne was demonstrated using a first- or second-generation ruthenium complex. When cycloalkenes bearing the alkyne part at the C-3 position were reacted with a first-generation ruthenium-carbene complex under an atmosphere of ethylene, ROM-RCM proceeded smoothly to give skeletal reorganized products in good yields. In this reaction, cycloalkene-ynes having terminal alkyne were suitable. On the other hand, when cycloalkenes bearing the alkyne part at the C-1 position were treated with a second-generation ruthenium-carbene complex, ROM-RCM proceeded smoothly to give bicyclic compounds and/or dimeric compounds in good yields. (C) 2004 Elsevier Ltd. All rights reserved.