N-(buta-2,3-dienyl)-4-methyl-N-(3-oxobutyl)benzenesulfonamide | 420132-32-7

• 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-(buta-2,3-dienyl)-4-methyl-N-(3-oxobutyl)benzenesulfonamide
• CAS: 420132-32-7
• 化学式: C₁₅H₁₉NO₃S
• 分子量: 293.387
• InChiKey: GLFWQCDOKKPDDT-UHFFFAOYSA-N

物化性质

• 沸点：
  444.4±55.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(buta-2,3-dienyl)-4-methyl-N-(3-oxobutyl)benzenesulfonamide 在 甲醇 、 potassium carbonate 、 三苯基膦 、 联硼酸频那醇酯 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以69%的产率得到4-methyl-1-tosyl-3-vinylpiperidin-4-ol
  参考文献：
  名称：

  铜催化的级联碳硼化和原脱硼烷基化作用的异戊二烯系酮胺的非对映选择性还原环化

  摘要：

  已开发出一种铜催化的级联方法，以高度非对映选择性的方式合成3-羟基吡咯烷衍生物。该反应通过由烯丙基形成硼烷基化烯丙基铜中间体而进行；参见表1。中间体进行分子内非对映选择性环化，然后级联铜催化的原脱硼基作用，得到3-羟基吡咯烷。该方法可以扩展到六元哌啶类似物的合成。进行了一系列对照实验，以确认在室温下铜催化的硼酸化均烯丙基醇的原基去基化反应。

  DOI：

  10.1002/bkcs.12241
• 作为产物：
  描述：

  N-(but-3-ynyl)-N-(buta-2,3-dienyl)-4-methylbenzenesulfonamide 在 mercury(II) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 以8%的产率得到N-(buta-2,3-dienyl)-4-methyl-N-(3-oxobutyl)benzenesulfonamide
  参考文献：
  名称：

  Mercury(II) Triflate-Catalyzed Cycloisomerization of Allenynes to Allenenes

  摘要：

  [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.

  DOI：

  10.1021/jo701591e

文献信息

• Enantioselective nickel-catalyzed arylative and alkenylative intramolecular 1,2-allylations of tethered allene–ketones
  作者：Riccardo Di Sanza、Thi Le Nhon Nguyen、Naeem Iqbal、Stephen P. Argent、William Lewis、Hon Wai Lam

  DOI：10.1039/c9sc05246a

  日期：——

  Chiral tertiary-alcohol-containing aza- and carbocycles are produced in high diastereo- and enantioselectivities by the nickel-catalyzed reaction of tethered allene–ketones with (hetero)arylboronic acids or potassium vinyltrifluoroborate.

  通过镍催化作用，将带有烯丙基酮的环氮和环碳化合物与（杂）芳基硼酸或三氟硼酸乙烯钾反应，高对映选择性和对映选择性地产生手性三级醇化合物。
• Palladium-Catalyzed Tandem Cyclization of Allenyl-Aldehydes and -Ketones with Aryl Iodides and Bu₃SnSnBu₃
  作者：Young-Hwan Ha、Suk-Ku Kang

  DOI：10.1021/ol025557t

  日期：2002.4.1

  [GRAPHICS]The arylative cyclization of allenyl-aidehydes with aryl iodides and hexa-n-butyldistannane to form substituted cyclopentanols and cyclohexanols by tandem palladium-catalyzed carbostannylation and allylation was achieved under mild conditions.
• Palladium−Indium-Mediated Arylative Cyclization of Allenyl-Aldehydes and -Ketones
  作者：Suk-Ku Kang、Sung-Won Lee、Jihyun Jung、Yoongho Lim

  DOI：10.1021/jo020017v

  日期：2002.6.1

  The arylative cyclization of allenyl-aldehydes and -ketones to form homoallylic cyclopentanols and cyclohexanols by the palladium-catalyzed and indium-mediated Babier allylation is described.
• Silylative Carbocyclization of Allenyl-carbonyl Units with Et₃SiH Catalyzed by Rhodium:  Cis-Stereoselective Synthesis of Homoallylic Cycloalkanols
  作者：Suk-Ku Kang、Young-Taek Hong、Joon-Hwan Lee、Won-Yeol Kim、Inhee Lee、Chan-Mo Yu

  DOI：10.1021/ol034787k

  日期：2003.8.1

  GraphicsA new procedure for the synthesis of cis-2-triethylsilylvinyl-cyclopentanois and -cyclohexanols from allenyl-aldehydes and -ketones with Et-3-SiH through rhodium-catalyzed silylative carbocyclization is described. The use of Rh(acac)(CO)(2) (1 mol %) to promote the reaction results in a mild and convenient protocol for the three-component assembly.
• Palladium-Catalyzed Regio- and Diastereoselective Tandem Silastannylation/Allyl Addition of Allene Aldehydes and Allene Ketones: Synthesis of cis Cyclopentanols and Cyclohexanols This work was supported by the National Research Laboratory Project administrated by the Ministry of Science and Technology and KOSEF-CMDS.
  作者：Suk-Ku Kang、Young-Hwan Ha、Byung-Soo Ko、Yoongho Lim、Jihyun Jung

  DOI：10.1002/1521-3773(20020118)41:2<343::aid-anie343>3.0.co;2-1

  日期：2002.1.18