N-(penta-2,3-dienyl)-N-(prop-2-ynyl)tosylamine | 491862-38-5

• 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-(penta-2,3-dienyl)-N-(prop-2-ynyl)tosylamine
• 英文别名: 4-methyl-N-(2,3-pentadienyl)-N-(2-propynyl)benzenesulfonamide
• CAS: 491862-38-5
• 化学式: C₁₅H₁₇NO₂S
• 分子量: 275.371
• InChiKey: NELCUYLWNYRZFM-UHFFFAOYSA-N

物化性质

• 熔点：
  45-46 °C
• 沸点：
  404.3±55.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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-(penta-2,3-dienyl)-N-(prop-2-ynyl)tosylamine 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 氘代甲苯 为溶剂， 反应 6.0h， 以93%的产率得到3-methylene-1-(4-toluenesulfonyl)-4-vinyl-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  用于交叉共轭三烯的快速立体选择性组装的铑（I）催化的甲醛醛烯反应

  摘要：

  已经发现了铑（I）催化的丙二烯阿尔德烯反应来制备交叉共轭三烯。目前正在调查范围和限制，并报告迄今为止获得的结果。该方法通过容忍末端和内部炔烃、羟基、磺酰胺、醚和二酯基团显示出诱人的官能团相容性。通过前所未有的铱（I）催化的阿尔德烯反应，在提高烯烃侧链的立体选择性方面取得了进展。

  DOI：

  10.1021/ja027588p
• 作为产物：
  描述：

  4-methyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.25h， 生成 N-(penta-2,3-dienyl)-N-(prop-2-ynyl)tosylamine
  参考文献：
  名称：

  Pd-Catalyzed Borylsilylative Cyclization of 1,6-Allenynes

  摘要：

  DOI：

  10.1021/acs.orglett.2c02878

文献信息

• Total Syntheses of the Reported Structures of Curcusones I and J through Tandem Gold Catalysis
  作者：Yong Li、Mingji Dai

  DOI：10.1002/anie.201706845

  日期：2017.9.11

  Total syntheses of the reported structures of the rhamnofolane diterpene natural products curcusones I and J in racemic form were achieved. The synthetic strategy features a novel tandem gold‐catalyzed furan formation and furan–allene [4+3] cycloaddition to build the 5,7‐fused ring system with an oxa‐bridge in one step, and a stereoselective exo‐Diels–Alder reaction to form the 6‐membered ring. The

  实现了外消旋形式的鼠李叶烷二萜天然产物curcusone I和J的报道结构的全合成。该合成策略采用新型串联金催化呋喃形成和呋喃-丙二烯[4+3]环加成，一步构建带有氧杂桥的5,7-稠环系统，以及立体选择性外-狄尔斯-阿尔德反应形成6元环。新开发的串联金催化非常通用并且可以放大。我们的合成表明需要对 curcusones I 和 J 进行结构修改。
• Highly efficient [2 + 2] intramolecular cyclizations of allenynes under microwave irradiation: construction of fused bicyclic compounds
  作者：Chang Ho Oh、Arun Kumar Gupta、Dai In Park、Nakjoong Kim

  DOI：10.1039/b508306k

  日期：——

  A palladium [2 + 2] cycloaddition of 1,6- and 1,7-allenyne carboxylates and microwave-mediated [2 + 2] cycloaddition of various 1,n-allenynes were developed and, particularly, the microwave irradiated [2 + 2] cycloaddition of allenynes can provide a simple, general and eco-friendly synthetic method to fused bicyclo[m,2,0]alkadienes.

  1,6-和1,7-炔烃羧酸的钯[2 + 2]环加成反应以及各种1，n-炔烃的微波介导的[2 + 2]环加成反应，特别是微波照射的[2 + 2炔烃的环加成反应可提供一种简单，通用且环保的合成方法，以稠合双环[m，2,0]链二烯。
• Molybdenum-Catalyzed Ring-Closing Metathesis of Allenynes
  作者：Masahiro Murakami、Sho Kadowaki、Takanori Matsuda

  DOI：10.1021/ol0514348

  日期：2005.9.1

  A ring-closing metathesis reaction of allenynes occurred at room temperature in the presence of a molybdenum alkylidene complex to give ring-closed vinylallenes. The vinylallene skeletons were constructed by a metathesis-type reaction between the alkyne moiety and the proximal carbon-carbon double bond of the allene moiety.
• Mercury(II) Triflate-Catalyzed Cycloisomerization of Allenynes to Allenenes
  作者：So Hee Sim、Sang Ick Lee、Junhyeok Seo、Young Keun Chung

  DOI：10.1021/jo701591e

  日期：2007.12.1

  [Graphics]Cycloisomerizations of allenynes to allenenes have been studied in the presence of catalytic amounts of [Hg(OTf)(2)] in acetonitrile. The catalytic system is quite effective for terminal 1,6-allenynes: allenenes were obtained in reasonable to high yields. However, treatment of allenynes with disubstituents at the allenic terminal carbon yielded a triene and/ or allenene as a major product(s) depending upon the substituents.
• A Rhodium(I)-Catalyzed Formal Allenic Alder Ene Reaction for the Rapid and Stereoselective Assembly of Cross-Conjugated Trienes
  作者：Kay M. Brummond、Hongfeng Chen、Peter Sill、Lingfeng You

  DOI：10.1021/ja027588p

  日期：2002.12.1

  A rhodium(I)-catalyzed allenic Alder ene reaction to prepare cross-conjugated trienes has been discovered. The scope and limitations are currently being investigated, and the results obtained to date are reported on. This method shows enticing functional group compatibility by tolerating terminal and internal alkynes, hydroxyl, sulfonamide, ether, and diester groups. Progress has been made to increase

  已经发现了铑（I）催化的丙二烯阿尔德烯反应来制备交叉共轭三烯。目前正在调查范围和限制，并报告迄今为止获得的结果。该方法通过容忍末端和内部炔烃、羟基、磺酰胺、醚和二酯基团显示出诱人的官能团相容性。通过前所未有的铱（I）催化的阿尔德烯反应，在提高烯烃侧链的立体选择性方面取得了进展。