methyl (2E,4Z)-5-iodo-4-methylpenta-2,4-dienoate | 444760-03-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2E,4Z)-5-iodo-4-methylpenta-2,4-dienoate
• CAS: 444760-03-6
• 化学式: C₇H₉IO₂
• 分子量: 252.052
• InChiKey: IAHWJDBHEWSPSS-ICWBMWKASA-N

物化性质

• 沸点：
  246.8±23.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 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 在 4-二甲氨基吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (2E,4Z)-5-Iodo-4-methyl-penta-2,4-dienoic 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
• 作为产物：
  描述：

  甲氧羰基亚甲基三苯基正膦 、 (Z)-3 -iodo-2-methylacrylaldehyde 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到methyl (2E,4Z)-5-iodo-4-methylpenta-2,4-dienoate
  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+

文献信息

• Total Synthesis of (−)-Archazolid B
  作者：Paul A. Roethle、Ingrid T. Chen、Dirk Trauner

  DOI：10.1021/ja0733033

  日期：2007.7.1

  A highly convergent synthesis of archazolid B, a potent and highly selective V-ATPase inhibitor, is described. A relay ring-closing metathesis reaction was used to form the 24-membered macrocyclic lactone, whereas the sensitive cis-triene moiety of the archazolids was assembled with a modified Stille coupling.
• 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.