1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene | 444760-02-5

• 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: 1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene
• 英文别名: 1-[(1E,3Z)-4-iodo-2-methylpenta-1,3-dienyl]-4-nitrobenzene
• CAS: 444760-02-5
• 化学式: C₁₂H₁₂INO₂
• 分子量: 329.137
• InChiKey: YHNNKWGDGSUUIK-AZRUORMVSA-N

物化性质

• 沸点：
  368.9±25.0 °C(Predicted)
• 密度：
  1.614±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (2E,4Z)-5-iodo-4-methylpenta-2,4-dienoate 、 1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene 在 四(三苯基膦)钯 、 双(乙腈)氯化钯(II) 六甲基二锡 、 N,N-二异丙基乙胺 作用下， 以 苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以85 mg的产率得到methyl (1RS,6SR,7RS,8RS)-1,3,5-trimethyl-8-(4-nitrophenyl)bicyclo[4.2.0]octa-2,4-diene-7-carboxylate
  参考文献：
  名称：

  “Endo” and “Exo” Bicyclo[4.2.0]-octadiene Isomers from the Electrocyclization of Fully Substituted Tetraene Models for SNF 4435C and D. Control of Stereochemistry by Choice of a Functionalized Substituent

  摘要：

  [GRAPHICS]A tandem electrocyclic closure, perceived as the key step in a biomimetic approach to SNF 4435C and D, was tested with 1,1,8-trisubstituted tetraene substrates. The ratio of endo:exo products could be controlled by the choice of the R-z substituent at C-1. On the basis of these results, a short stereoselective route to an advanced SNF 4435 intermediate was devised.

  DOI：

  10.1021/ol036048+
• 作为产物：
  描述：

  对硝基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 3.67h， 生成 1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene
  参考文献：
  名称：

  “Endo” and “Exo” Bicyclo[4.2.0]-octadiene Isomers from the Electrocyclization of Fully Substituted Tetraene Models for SNF 4435C and D. Control of Stereochemistry by Choice of a Functionalized Substituent

  摘要：

  [GRAPHICS]A tandem electrocyclic closure, perceived as the key step in a biomimetic approach to SNF 4435C and D, was tested with 1,1,8-trisubstituted tetraene substrates. The ratio of endo:exo products could be controlled by the choice of the R-z substituent at C-1. On the basis of these results, a short stereoselective route to an advanced SNF 4435 intermediate was devised.

  DOI：

  10.1021/ol036048+
• 作为试剂：
  描述：

  (2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester 、 、 六甲基二锡 、 1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene 在 双(乙腈)氯化钯(II) 四(三苯基膦)钯 、 N,N-二异丙基乙胺 、 1-((1E,3Z)-4-iodo-2-methyl-penta-1,3-dienyl)-4-nitrobenzene 作用下， 以 苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (1S,6R,7R,8S)-1,3,5-Trimethyl-8-(4-nitro-phenyl)-bicyclo[4.2.0]octa-2,4-diene-7-carboxylic acid (1R,2R)-2-(naphthalene-2-sulfonyl)-cyclohexyl ester 、
  参考文献：
  名称：

  Cleavable Chiral Auxiliaries in 8π (8π, 6π) Electrocyclizations

  摘要：

  Low to moderate diastereoselectivity was observed in the 8 pi electrocyclization of a series of chiral auxiliary-bearing tetraenic esters. In the 8-arylmenthyl series, diastereomeric products were separated by chromatography.

  DOI：

  10.1021/ol061328l

文献信息

• Synthetic Studies toward SNF4435 C and SNF4435 D
  作者：Christopher M. Beaudry、Dirk Trauner

  DOI：10.1021/ol026069o

  日期：2002.6.1

  A synthetic approach toward the immunosuppressants SNF3345 C and SNF4435 D featuring a tandem Stille coupling/electrocyclization cascade is described.
• The Total Synthesis of (−)-SNF4435 C and (+)-SNF4435 D
  作者：Kathlyn A. Parker、Yeon-Hee Lim

  DOI：10.1021/ja044733l

  日期：2004.12.1

  The size and positioning of substituents on a tetraene, along with the Woodward-Hoffmann rules, control the relative stereochemistry at the four adjacent chiral centers that are generated in the 8pi/6pi electrocyclization cascade. A biomimetic synthesis of (-)-SNF4435 C and (+)-SNF4435 D exploits these steric effects and allows confirmation of the predicted absolute stereochemistry of the natural products.