(Z)-Non-2-en-4-ynoic acid ethyl ester | 64576-91-6

• 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: (Z)-Non-2-en-4-ynoic acid ethyl ester
• 英文别名: Ethyl non-2-en-4-ynoate；ethyl non-2-en-4-ynoate
• CAS: 64576-91-6
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: QSCUDZDJQRVKFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 2 Torr)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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

• 作为产物：
  描述：

  1-碘-1-己炔 、 (Z)-2-ethoxycarbonylethenyl zinc iodide 在 二甲基硫 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以81%的产率得到(Z)-Non-2-en-4-ynoic acid ethyl ester
  参考文献：
  名称：

  官能化烯基锌，铜和铬有机金属化合物的制备和反应性

  摘要：

  Beta-halogeno-alpha,beta-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45-degrees-C, 1-4h). These functionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97% yield. The addition of a THF solution of CuCN.2LiCl to 2a affords the corresponding organocopper derivatives 2b which react with electrophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfunctional unsaturated carbonyl compounds in 71-95% yield. The insertion of chromium (II) chloride to beta-iodo and to some beta-(p-tosyl)enones in DMF furnishes new functionalized chromium (III) organometallics 2c which react with aldehydes providing gamma-hydroxy unsaturated carbonyl derivatives in 40-91% yield. The synthetic scope and the limitations of this methodology are discussed.

  DOI：

  10.1016/s0040-4020(01)80504-4

文献信息

• A Simple One-pot Organometallic Formylation/Trapping Sequence Using<i>N</i>-Formylcarbazole
  作者：Darren J. Dixon、Amanda C. Lucas

  DOI：10.1055/s-2004-822896

  日期：——

  Treatment of a range of sp3-, sp2- and sp-nucleophiles with N-formyl carbazole leads to the formation of the metastable anionic carbazole carbinols. In the presence of a second nucleophilic reagent such as phosphonoacetate or an organolithium, these collapse on warming to the aldehyde which is trapped in situ to afford the α,β-unsaturated esters or secondary carbinols respectively.

  通过N-甲酰咔唑与一系列sp3-、sp2-和sp-亲核试剂反应，形成了亚稳态阴离子咔唑醇。在存在另一种亲核试剂（如膦酰乙酸酯或有机锂试剂）的情况下，通过加热使这些产物转化为醛，并原位捕获得到α,β-不饱和酯或二级醇。
• Preparation and reactivity of functionalized alkenyl-zinc, -copper, and -chromium organometallics
  作者：Paul Knochel、C. Janakiram Rao

  DOI：10.1016/s0040-4020(01)80504-4

  日期：1993.1

  Beta-halogeno-alpha,beta-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45-degrees-C, 1-4h). These functionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97% yield. The addition of a THF solution of CuCN.2LiCl to 2a affords the corresponding organocopper derivatives 2b which react with electrophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfunctional unsaturated carbonyl compounds in 71-95% yield. The insertion of chromium (II) chloride to beta-iodo and to some beta-(p-tosyl)enones in DMF furnishes new functionalized chromium (III) organometallics 2c which react with aldehydes providing gamma-hydroxy unsaturated carbonyl derivatives in 40-91% yield. The synthetic scope and the limitations of this methodology are discussed.