2-methyl-2,4-pentadienal | 54716-10-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-2,4-pentadienal
• 英文别名: (Z)-2-methyl-penta-2,4-dienal；(2Z)-2-methylpenta-2,4-dienal
• CAS: 54716-10-8
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: GPOYSKDINJWXAG-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-2,4-pentadienal 在 草酰氯 、 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (Z)-N-benzyl-2-iodo-N-(2-methylpenta-2,4-dien-1-yl)benzamide
  参考文献：
  名称：

  Synergistic Palladium/Copper‐Catalyzed 1,4‐Difunctionalization of 1,3‐Dienes for Stereodivergent Construction of 1,5‐Nonadjacent Stereocenters

  摘要：

  The construction of two distal stereocenters through a single catalytic process is of great interest in organic synthesis. While there are some successful reports regarding stereodivergent preparation of 1,3‐ or 1,4‐stereocenters, the more challenged 1,5‐nonadjacent stereocenters have never been achieved in a stereodivergent fashion. Herein we describe a synergistic palladium/copper catalysis for 1,4‐difunctionalization reactions of 1,3‐dienes, providing access to 1,5‐nonadjacent quaternary stereocenters. Because each of the two catalysts separately controlled one of the newly formed stereocenters, stereodivergent synthesis of all four diastereomers of the products could readily be achieved simply by choosing an appropriate combination of chiral catalysts. Experimental and computational studies supported a mechanism involving a Heck/Tsuji–Trost cascade reaction, and the origins of the stereoselectivity were elucidated.

  DOI：

  10.1002/anie.202402843
• 作为产物：
  描述：

  2-methyl-2,4-pentadienol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 2-methyl-2,4-pentadienal
  参考文献：
  名称：

  Synergistic Palladium/Copper‐Catalyzed 1,4‐Difunctionalization of 1,3‐Dienes for Stereodivergent Construction of 1,5‐Nonadjacent Stereocenters

  摘要：

  The construction of two distal stereocenters through a single catalytic process is of great interest in organic synthesis. While there are some successful reports regarding stereodivergent preparation of 1,3‐ or 1,4‐stereocenters, the more challenged 1,5‐nonadjacent stereocenters have never been achieved in a stereodivergent fashion. Herein we describe a synergistic palladium/copper catalysis for 1,4‐difunctionalization reactions of 1,3‐dienes, providing access to 1,5‐nonadjacent quaternary stereocenters. Because each of the two catalysts separately controlled one of the newly formed stereocenters, stereodivergent synthesis of all four diastereomers of the products could readily be achieved simply by choosing an appropriate combination of chiral catalysts. Experimental and computational studies supported a mechanism involving a Heck/Tsuji–Trost cascade reaction, and the origins of the stereoselectivity were elucidated.

  DOI：

  10.1002/anie.202402843

文献信息

• Synthesis, Absolute Configurations, and Biological Activities of Floral Scent Compounds from Night-Blooming Araceae
  作者：Patrick Stamm、Florian Etl、Artur Campos D. Maia、Stefan Dötterl、Stefan Schulz

  DOI：10.1021/acs.joc.1c00145

  日期：2021.4.2

  dehydrojasmone, isojasmol, and isojasmyl acetate, floral scent compounds from night-blooming Araceae, were synthesized in a scalable synthesis employing conjugate addition with a selenoacetal as the key step. The stereoselective strategy with subsequent enzymatic kinetic resolution allowed determining the absolute configuration of the natural compounds by GC on a chiral phase. The homoterpene (E)-4,8-dimethyl-1

  夜茉莉科植物的稀有茉莉衍生物，脱氢茉莉酮，异茉莉酮和乙酸异茉莉酯，花香化合物，是通过可扩展的合成方法合成的，该方法使用缀合物加硒代乙醛作为关键步骤。具有随后的酶动力学拆分的立体选择策略允许通过GC在手性相上确定天然化合物的绝对构型。通过α-区域选择性醛烯丙基化获得另一种不常见的香气化合物高萜烯（E）-4,8-​​二甲基-1,3,7-壬二烯基-5-基乙酸酯。在现场试验中对脱氢茉莉酮和异茉莉酮的生物学活性进行了研究，结果表明，这些独特的挥发物能够选择性地吸引特定的环脑金龟子甲虫传粉者。
• SPANGLER, CH. W.;TAN, R. P. K.;GIBSON, R. S.;MCCOY, R. K., SYNTH. COMMUN., 1985, 15, N 5, 371-376
  作者：SPANGLER, CH. W.、TAN, R. P. K.、GIBSON, R. S.、MCCOY, R. K.

  DOI：——

  日期：——