N-buta-2,3-dienyl-4-methyl-N-(2-oxopropyl)benzenesulfonamide | 420132-21-4

• 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-buta-2,3-dienyl-4-methyl-N-(2-oxopropyl)benzenesulfonamide
• 英文别名: N-(2,3-butadienyl)-4-methyl-N-(2-oxopropyl)benzenesulfonamide；Agn-PC-006sdu
• CAS: 420132-21-4
• 化学式: C₁₄H₁₇NO₃S
• 分子量: 279.36
• InChiKey: SJFCMHUUXQOEJV-UHFFFAOYSA-N

物化性质

• 沸点：
  421.7±55.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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-(2-oxopropyl)benzenesulfonamide 在 acetylacetonatodicarbonylrhodium(l) 、 一氧化碳 、 溴 作用下， 以 乙醚 、 二氯甲烷 为溶剂， -78.0~70.0 ℃ 、1.01 MPa 条件下， 生成 4-(1-bromo-vinyl)-3-methyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol
  参考文献：
  名称：

  Silylative Carbocyclization of Allenyl-carbonyl Units with Et₃SiH Catalyzed by Rhodium:  Cis-Stereoselective Synthesis of Homoallylic Cycloalkanols

  摘要：

  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.

  DOI：

  10.1021/ol034787k

文献信息

• cis-Stereoselective nickel-catalyzed cyclization/alkylation and arylation reactions of allenyl-aldehydes and -ketones with organozinc reagentsElectronic supplementary information (ESI) available: typical procedures, NMR-data, and X-ray data. See http://www.rsc.org/suppdata/cc/b2/b207620a/
  作者：Suk-Ku Kang、Seok-Keun Yoon

  DOI：10.1039/b207620a

  日期：2002.11.4

  Highly stereoselective alkylative and arylative cyclization reactions of allenyl-aldehydes and -ketones with organozinc reagents occur efficiently in the presence of catalytic Ni(COD)2 to afford cis-fused homoallylic cyclopentanols.

  在催化Ni（COD）2的存在下，烯丙基-醛和-酮与有机锌试剂的高度立体选择性烷基化和芳基化环化反应可有效发生，以提供顺式稠合均烯丙基环戊醇。
• 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。
• Enantioselective Arylative Cyclization of Allenyl Aldehydes with Arylboronic Acids under Pd(II)-diphosphine Catalysis
  作者：Hirokazu Tsukamoto、Tomotaka Matsumoto、Yoshinori Kondo

  DOI：10.1021/ol702966j

  日期：2008.3.1

  A Pd(OAc)(2)-SEGPHOS combination catalyzes the first enantioselective arylative cyclization of allenyl aldehydes with arylboronic acids to provide cis-fused five- and six-membered cyclic homoallylic alcohols. The excellent diastereo- and enantioselectivity and the fact that the reaction proceeds at room temperature in the absence of any additives make the process highly practical.
• Synthesis of<i>α</i>-Methylene-<i>γ</i>-butyrolactones: Ru-Catalyzed Cyclocarbonylation of Allenyl Aldehydes and Allenyl Ketones
  作者：Suk-Ku Kang、Kwang-Jin Kim、Young-Taek Hong

  DOI：10.1002/1521-3773(20020503)41:9<1584::aid-anie1584>3.0.co;2-y

  日期：2002.5.3
• 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.