methyl (Z)-non-3-enoate | 41654-16-4

• 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-3-enoate
• 英文别名: cis-Nonen-(3)-saeuremethylester；Methyl-3Z-nonenoat；Methyl 3-nonenoate, (3Z)-
• CAS: 41654-16-4
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: MTDCXFZGUVZRSQ-FPLPWBNLSA-N

物化性质

• 沸点：
  212.7±9.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)
• 物理描述：
  Liquid
• 溶解度：
  insoluble in water
• 折光率：
  1.432-1.442

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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-3-enoate 在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 methyl (Z)-2-diazonon-3-enoate
  参考文献：
  名称：

  铑（II）-乙烯基类胡萝卜素插入SiH键中。烯丙基硅烷的立体定向合成的新方法

  摘要：

  在有机硅烷的存在下，Rh 2（OAc）4催化的乙烯基重氮羰基化合物的分解立体定向地以良好的收率生成了相应的烯丙基硅烷。还考虑了不对称方法，以及将方法扩展到其他烯丙基系统的合成。

  DOI：

  10.1016/0040-4039(94)88508-7
• 作为产物：
  描述：

  3-壬炔-1-醇 在 Lindlar's catalyst jones reagent 、 氢气 作用下， 生成 methyl (Z)-non-3-enoate
  参考文献：
  名称：

  铑（II）-乙烯基类胡萝卜素插入SiH键中。烯丙基硅烷的立体定向合成的新方法

  摘要：

  在有机硅烷的存在下，Rh 2（OAc）4催化的乙烯基重氮羰基化合物的分解立体定向地以良好的收率生成了相应的烯丙基硅烷。还考虑了不对称方法，以及将方法扩展到其他烯丙基系统的合成。

  DOI：

  10.1016/0040-4039(94)88508-7

文献信息

• Direct C–C Bond Formation of Allylic Alcohols with CO₂ toward Carboxylic Acids by Photoredox/Nickel Dual Catalysis
  作者：Zhengning Fan、Shenhao Chen、Song Zou、Chanjuan Xi

  DOI：10.1021/acscatal.2c00418

  日期：2022.3.4

  Carboxylation of allylic alcohols with carbon dioxide is accomplished by photoredox/nickel dual catalysis, generating linear acids exclusively with good Z/E stereoselectivity. Hantzsch ester is employed as the reductant instead of stoichiometric metallic reductants, and the reaction can be conducted under room temperature with a blue LED light source. Mechanistic studies reveal that the presence of

  烯丙醇与二氧化碳的羧基化是通过光氧化还原/镍双重催化完成的，仅生成具有良好Z/E立体选择性的线性酸。采用 Hantzsch 酯代替化学计量的金属还原剂作为还原剂，反应可以在室温下用蓝色 LED 光源进行。机理研究表明，该催化体系中水的存在对反应的成功至关重要，并且反应更有可能在原位形成的烯丙基碳酸氢盐的氧化加成中进行。
• A Stereospecific Access to Allylic Systems Using Rhodium(II)−Vinyl Carbenoid Insertion into Si−H, O−H, and N−H Bonds
  作者：Priyadarshanie Bulugahapitiya、Yannick Landais、Liliana Parra-Rapado、Denis Planchenault、Valéry Weber

  DOI：10.1021/jo961952j

  日期：1997.3.1

  Rhodium-catalyzed decomposition of alpha-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding alpha-silyl, alpha-hydroxy, alpha-alkoxy, alpha-amino, and alpha-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral alpha-vinyldiazoesters and Doyle's chiral catalyst Rh-2(MEPY)(4). In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh-2(MEPY)(4)-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.
• Electron Transfer Profile of Cyclopropanone Acetals in the Nonirradiated Reaction with Tetracyanoethylene, Chloranil, and Dicyanodichlorobenzoquinone
  作者：Akira Oku、Manabu Abe、Masaharu Iwamoto

  DOI：10.1021/jo00103a043

  日期：1994.12

  The donor profiles of cyclopropanone acetals 1 and 2 were examined in the reactions with electron accepters (TCNE, DDQ, chloranil, and 1-cyanonaphthalene). With TCNE under nonirradiating conditions, an exclusive 2 + 2 cycloaddition took place stereospecifically with monosubstituted acetals 1a-c but nonstereospecifically with disubstituted acetals 1d,e. With quinones, a ring-opening of the cyclopropane and its coupling with the quinone took place to give the C (cyclopropane)-O (quinone) adduct 9 (with chloranil) or 10 (with DDQ), the latter of which underwent the elimination of a phenol to produce unsaturated esters 5 and 6. In addition, the intervention of the C (cyclopropane)-C (quinone) adduct 14 (with chloranil) or 15 (with DDQ), both as the precursor of 5 and 6, was also postulated. With 1-cyanonaphthalene, under photolysis, the cis/trans isomerization of 1 and 2 occurred. The results provided evidences that cyclopropanone acetals, in general, are prone to function as donors. The mechanism of the reaction with quinones, in particular, was investigated in detail.
• MITTELBACH, MARTIN;POKLUKAR, NORBERT, CHEM. AND PHYS. LIPIDS , 55<!>,(1990) N, C. 67-72
  作者：MITTELBACH, MARTIN、POKLUKAR, NORBERT

  DOI：——

  日期：——