methyl (Z)-non-2-en-4-ynoate | 75066-87-4

• 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 (Z)-non-2-en-4-ynoate
• 英文别名: methyl (Z)-2-nonen-4-ynoate
• CAS: 75066-87-4
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: VFZSBDWDBGNHLW-HJWRWDBZSA-N

物化性质

• 沸点：
  230.3±23.0 °C(Predicted)
• 密度：
  0.955±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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 (Z)-non-2-en-4-ynoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 2-nonen-4-ynal
  参考文献：
  名称：

  Palladium-Catalyzed Alkoxycarbonylation of (Z)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates

  摘要：

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.

  DOI：

  10.1021/ol102989q
• 作为产物：
  描述：

  (Z)-3-碘丙烯酸甲酯 、 1-己炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 15.0h， 以85%的产率得到methyl (Z)-non-2-en-4-ynoate
  参考文献：
  名称：

  铑（III）催化的C ？的1,3-烯炔的全碳[3 + 3]氧化态。H功能化和1,4迁移

  摘要：

  含烯丙基氢的1，3-烯炔顺式延伸至炔烃，在铑（III）催化的全碳[3 + 3]氧化环中作为三碳组分生成螺二醛。这些反应的拟议机制涉及烯基至烯丙基1,4-铑（III）的迁移。

  DOI：

  10.1002/anie.201503978

文献信息

• Selective synthesis of natural and unnatural 5,6-disubstituted 2(2H)-pyranones via iodolactonization of 5-substituted (Z)-2-en-4-ynoic acids
  作者：Fabio Bellina、Matteo Biagetti、Adriano Carpita、Renzo Rossi

  DOI：10.1016/s0040-4020(01)00139-9

  日期：2001.4

  -2(5H)-furanones and 6-substituted 5-iodo-2(2H)-pyranones in which these last compounds are the major products. The 5-iodo-2(2H)-pyranones, which are easily separated chromatographically from the corresponding regioisomers, are able to undergo Stille-type reactions with a variety of organotin compounds to give 5,6-disubstituted 2(2H)-pyranones in moderate to good yields. One of these compounds, i.e

  5-取代的（Z）-2-en-4-壬酸与CH 3 CN中的碘和NaHCO 3或与CH 2 Cl 2中的ICl反应，得到（E）-5-（1-碘亚烷基）-2的混合物（5 H）-呋喃酮和6-取代的5-碘-2（2 H）-吡喃酮类化合物是其中的主要产物。5-碘-2-（2 H）-吡喃酮很容易从色谱上从相应的区域异构体中分离出来，能够与多种有机锡化合物进行Stille型反应，从而生成5,6-二取代的2（2 H）-吡喃酮的产量中等至良好。这些化合物之一，即5-（1-丁炔基）-2（2 H）-吡喃酮已被用作真菌培养物LL-11G219产生的两种物质的直接前体，它们起着雄激素配体的作用，即（Z）-5-（1-丁烯基）-6-甲基-2（2 H）-吡喃酮和5-丁基-6-甲基-2（2 H）-吡喃酮。
• Lewis acid–base 1,2-addition reactions: synthesis of pyrylium borates from en-ynoate precursors
  作者：Lewis C. Wilkins、Hugh B. Hamilton、Benson M. Kariuki、A. Stephen K. Hashmi、Max M. Hansmann、Rebecca L. Melen

  DOI：10.1039/c5dt03340c

  日期：——

  Treatment of methyl (Z)-2-alken-4-ynoates with the strong Lewis acid tris(pentafluorophenyl) borane, B(C6F5)3, yield substituted zwitterionic pyrylium borate species via an intramolecular 6-endo-dig cyclisation reaction.

  用强路易斯酸三（五氟苯基）硼烷B（C 6 F 5）3处理（Z）-2-链烯基-4-炔酸甲酯，通过分子内6-内挖环化反应生成取代的两性离子硼酸吡啶盐物种。
• A convenient stereoselective synthesis of conjugated (2Z)-EN-4-ynoic and (2Z,4Z)- and (2Z,4E)-dienoic acid derivatives from propiolic acid derivatives
  作者：Xiyan Lu、Xiaoling Huang、Shengming Ma

  DOI：10.1016/s0040-4039(00)92235-4

  日期：1992.4

  The palladium-catalyzed one-pot sequential reaction of propiolic acid derivatives with lithium halides first, and then with terminal alkynes or alkenes affords conjugated (2Z) -en-4-ynoic and (2Z,4Z)- and (2Z,4E)- dienoic acid derivatives with high stereoselectivity.

  钯催化的丙酸衍生物与卤化锂的一锅顺序反应，然后与末端炔烃或烯烃进行单锅顺序反应，得到共轭的（2Z）-en-4-炔酸和（2Z，4Z）-和（2Z，4E）-具有高立体选择性的二烯酸衍生物。
• Palladium-catalyzed triethylammonium formate reductions. 4. Reduction of acetylenes to cis-monoenes and hydrogenolysis of tertiary allylic amines
  作者：John R. Weir、Babu A. Patel、Richard F. Heck

  DOI：10.1021/jo01312a021

  日期：1980.11
• A General and Facile Synthesis of Substituted Furans by Palladium-Catalyzed Cycloisomerization of (<i>Z</i>)-2-En-4-yn-1-ols
  作者：Bartolo Gabriele、Giuseppe Salerno、Egidio Lauria

  DOI：10.1021/jo990847h

  日期：1999.10.1

  A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 degrees C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.