ethyl (2E,4E)-2,4-dimethyl-2,4-heptadienoate | 62332-69-8

• 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: ethyl (2E,4E)-2,4-dimethyl-2,4-heptadienoate
• 英文别名: Ethyl e,e-2,4-dimethylhepta-2,4-dienoate；ethyl (2E,4E)-2,4-dimethylhepta-2,4-dienoate
• CAS: 62332-69-8
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: WIVKHDMDKQZPOY-FIFLTTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  ethyl (2E,4E)-2,4-dimethyl-2,4-heptadienoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 14.0h， 以90%的产率得到(2E,4E)-2,4-dimethyl-2,4-heptadien-1-ol
  参考文献：
  名称：

  Dahmann, Georg; Hoffmann, Reinhard W., Liebigs Annalen der Chemie, 1994, # 8, p. 837 - 846

  摘要：

  DOI：
• 作为产物：
  描述：

  三乙基2-膦酰基丙酯 、 2-甲基-2-戊烯醛 在 lithium tert-butoxide 作用下， 以 正己烷 为溶剂， 反应 1.25h， 以98%的产率得到ethyl (2E,4E)-2,4-dimethyl-2,4-heptadienoate
  参考文献：
  名称：

  IMPROVED HORNER-WADSWORTH-EMMONS PREPARATION OF α-METHYL- OR α-ETHYL-α,β-UNSATURATED ESTERS FROM ALDEHYDES

  摘要：

  The E-isomer selectivity of the Horner-Wadsworth-Emmons olefination of aldehydes to form alpha -methyl- or alpha -ethyl-alpha,beta -unsaturated esters has been improved by using lithium tert-butoxide as the base, triethyl-2-phosphonopropionate or triethyl-2-phosphonobutyrate as the phosphonate, an aldehyde, and hexane as the reaction solvent. Greater E-isomer selectivity was observed in the formation of alpha -methyl-alpha,beta -unsaturated esters than alpha -ethyl-alpha,beta -unsaturated esters. These compounds are useful intermediates for the synthesis of insect pheromones and natural products.

  DOI：

  10.1081/scc-100000184

文献信息

• An efficient ketone-catalyzed asymmetric epoxidation using hydrogen peroxide (H 2 O 2 ) as primary oxidant
  作者：Lianhe Shu、Yian Shi

  DOI：10.1016/s0040-4020(01)00362-3

  日期：2001.6

  High enantioselectivities have been obtained for asymmetric epoxidation of olefins using a fructose-derived chiral ketone (5) as catalyst and hydrogen peroxide as primary oxidant.

  使用果糖衍生的手性酮（5）作为催化剂，过氧化氢作为主要氧化剂，对于烯烃的不对称环氧化已经获得了高对映选择性。
• Highly Regio- and Enantioselective Monoepoxidation of Conjugated Dienes
  作者：Michael Frohn、Molly Dalkiewicz、Yong Tu、Zhi-Xian Wang、Yian Shi

  DOI：10.1021/jo9721195

  日期：1998.5.1

  This paper describes a highly effective and mild asymmetric monoepoxidation method for conjugated dienes using a fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. The regioselectivies and enantioslectivies are very high in most cases. For unsymmetrical dienes, the regioselectivity can be regulated by using steric and electronic control. The olefin substrates include trans-disubstituted and trisubstituted olefins that can bear a wide range of functional groups such as hydroxyl groups, TBS ethers, or esters. The enantiomeric excesses for the major monoepoxides range from 89% to 97%. The epoxidation is believed to proceed via a spiro mode.
• Dahmann, Georg; Hoffmann, Reinhard W., Liebigs Annalen der Chemie, 1994, # 8, p. 837 - 846
  作者：Dahmann, Georg、Hoffmann, Reinhard W.

  DOI：——

  日期：——
• IMPROVED HORNER-WADSWORTH-EMMONS PREPARATION OF α-METHYL- OR α-ETHYL-α,β-UNSATURATED ESTERS FROM ALDEHYDES
  作者：Richard J. Petroski、David Weisleder

  DOI：10.1081/scc-100000184

  日期：2001.1

  The E-isomer selectivity of the Horner-Wadsworth-Emmons olefination of aldehydes to form alpha -methyl- or alpha -ethyl-alpha,beta -unsaturated esters has been improved by using lithium tert-butoxide as the base, triethyl-2-phosphonopropionate or triethyl-2-phosphonobutyrate as the phosphonate, an aldehyde, and hexane as the reaction solvent. Greater E-isomer selectivity was observed in the formation of alpha -methyl-alpha,beta -unsaturated esters than alpha -ethyl-alpha,beta -unsaturated esters. These compounds are useful intermediates for the synthesis of insect pheromones and natural products.