2,3-dimethyl-2-butene-1-amine | 1173278-11-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,3-dimethyl-2-butene-1-amine
• 英文别名: Tetramethylethyleneamine；2,3-dimethylbut-2-en-1-amine
• CAS: 1173278-11-9
• 化学式: C₆H₁₃N
• 分子量: 99.1759
• InChiKey: BOECHSSNNYQCRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-dimethyl-2-butene-1-amine 在 碳酸氢钠 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 N-(2,3-dimethylbut-2-enyl)l-4-methyl-N-(prop-2-ynyl)benzenesulfonamide
  参考文献：
  名称：

  Methylprenyl and Prenyl Protection for Sulfonamides

  摘要：

  2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki-Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.

  DOI：

  10.1055/s-0034-1379428
• 作为产物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 氨 、 醋酸钯 、 三苯基膦 、 三乙基铵碘化物 生成 2,3-dimethyl-2-butene-1-amine
  参考文献：
  名称：

  ARMBRUSTER, R. W.;MORGAN, M. M.;SCHMIDT, J. L.;LAU, CHUN, MAN;RILEY, R. M+, ORGANOMETALLICS, 1986, 5, N 2, 234-237

  摘要：

  DOI：

文献信息

• Parallel and four-step synthesis of natural-product-inspired scaffolds through modular assembly and divergent cyclization
  作者：Hiroki Oguri、Haruki Mizoguchi、Hideaki Oikawa、Aki Ishiyama、Masato Iwatsuki、Kazuhiko Otoguro、Satoshi Ōmura

  DOI：10.3762/bjoc.8.105

  日期：——

  By emulating the universal biosynthetic strategy, which employs modular assembly and divergent cyclizations, we have developed a four-step synthetic process to yield a collection of natural-product-inspired scaffolds. Modular assembly of building blocks onto a piperidine-based manifold 6, having a carboxylic acid group, was achieved through Ugi condensation, N-acetoacetylation and diazotransfer, leading

  通过模仿采用模块化组装和发散环化的通用生物合成策略，我们开发了一个四步合成过程，以产生一系列受天然产物启发的支架。通过 Ugi 缩合、N-乙酰乙酰化和重氮转移，将构建块模块化组装到基于哌啶的歧管 6 上，具有羧酸基团，从而产生环化前体。The rhodium-catalyzed tandem cyclization and divergent cycloaddition gave rise to tetracyclic and hexacyclic scaffolds by the appropriate choice of dipolarophiles installed at modules 3 and 4. A different piperidine-based manifold 15 bearing an amino group was successfully applied to
• Divergent and Expeditious Access to Fused Skeletons Inspired by Indole Alkaloids and Transtaganolides
  作者：Haruki Mizoguchi、Hiroki Oguri、Kiyoshi Tsuge、Hideaki Oikawa

  DOI：10.1021/ol901020a

  日期：2009.7.16

  We report the development of a divergent synthetic process entailing four-step access to the elaborate fused skeletons reminiscent of aspidophytines and transtaganolides. A variety of branched precursors were synthesized on the basis of Ugl condensations and installation of diazoimide and subjected to rhodium-catalyzed tandem reactions. Switching of cyclization modes was demonstrated by the choice of the amine building blocks installed at site C.