(E)-undec-3-enoic acid | 56770-25-3

• 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: (E)-undec-3-enoic acid
• 英文别名: (E)-3-undecenoic acid；3-undecenoic acid；undec-3-enoic acid；Undec-3-ensaeure；trans-Undecen-(3)-saeure；Undecen-(3)-saeure；3E-undecenoic acid
• CAS: 56770-25-3
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: OQDNPLAISLNBNS-CMDGGOBGSA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  295.3±9.0 °C(Predicted)
• 密度：
  0.929±0.06 g/cm3(Predicted)
• LogP：
  3.892 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-undec-3-enoic acid 在 RhCl3 水 、 氢气 作用下， 以 苯 为溶剂， 30.0 ℃ 、101.32 kPa 条件下， 生成 十一烷酸
  参考文献：
  名称：

  加水引起的链烷二酸的新的区域选择性加氢

  摘要：

  通过将水与RhCl [P（p-tolyl）3] 3在苯中于1atm的氢气中加入水，可以实现3,8-壬二酸向8-壬烯酸的区域选择性加氢，而在没有水的情况下，反应主要是得到3-壬烯酸。新的选择性是由水对3位氢化作用的加速作用和对8位氢化作用的阻滞作用所引起的。

  DOI：

  10.1016/s0040-4039(00)61142-5
• 作为产物：
  描述：

  2-((E)-Dec-2-enyl)-2-hydroxy-malonic acid 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 生成 (E)-undec-3-enoic acid
  参考文献：
  名称：

  用氧代丙二酸二乙酯作为二氧化碳的亲烯当量进行烯羧化。烯丙基羧酸的合成

  摘要：

  在制备 une serie d'acides carboxyliques allyliques a partir des ocoxyliques par un processus en deux etapes 等价物 a: 1) une 反应 ene avec l'oxomalonate de diethyle conduisant a l'ester α-hydroxymalonique; 2) une bisdecarboxylation oxydante de ce dernier

  DOI：

  10.1021/ja00325a014

文献信息

• Combined Transition-Metal- and Organocatalysis: An Atom Economic C3 Homologation of Alkenes to Carbonyl and Carboxylic Compounds
  作者：Susanne T. Kemme、Tomáš Šmejkal、Bernhard Breit

  DOI：10.1002/chem.200903223

  日期：2010.3.15

  A combination of regioselective room‐temperature/ambient‐pressure hydroformylation (transition‐metal catalysis) and decarboxylative Knoevenagel reactions (organocatalysis) allowed for the development of an efficient, one‐pot C3 homologation of terminal alkenes to (E)‐α,β‐unsaturated acids and esters, (E)‐β,γ‐unsaturated acids, (E)‐α‐cyano acrylic acids, and α,β‐unsaturated nitriles. All reactions proceed

  区域选择性的室温/环境压力加氢甲酰化（过渡金属催化）和脱羧Knoevenagel反应（有机催化）的结合可以发展出末端烯烃到（E）-α，β-的高效一锅C3同源性。不饱和酸和酯，（E）-β，γ-不饱和酸，（E）-α-氰基丙烯酸和α，β-不饱和腈。所有反应均在温和条件下进行，可耐受各种官能团，并以良好的收率和出色的区域和立体控制效果提供不饱和羰基化合物。此外，（E的迭代C2同源性）-α，β-不饱和羧酸可以通过使用超分子催化剂进行脱羧加氢甲酰化，然后与有机催化剂进行脱羧Knoevenagel缩合反应来实现。
• Novel naphthoquinone derivatives and evaluation of their trypanocidal and leishmanicidal activities
  作者：Aline Alves dos Santos Naujorks、Adriano Olímpio da Silva、Rosangela da Silva Lopes、Sérgio de Albuquerque、Adilson Beatriz、Maria Rita Marques、Dênis Pires de Lima

  DOI：10.1039/c4ob01869a

  日期：——

  derivatives, 6 substituted 1,4-naphthoquinones and 6 heterocycle-fused naphthoquinones, as well as evaluation of their trypanocidal and leishmanicidal activities. Compounds 11a and 13a were active against the amastigote stage of T. cruzi and showed low cytotoxic effects. With respect to leishmanicidal assays, all compounds were inactive against the promastigote stages of L. chagasi and L. braziliensis

  在这里，我们报告了12种新的萘醌衍生物，6个取代的1,4-萘醌和6个杂环稠合的萘醌的合成，以及它们的锥虫杀螨和利什曼杀虫活性的评估。化合物11A和13A是有效对抗的无鞭毛体阶段锥虫和显示出低细胞毒性效应。相对于leishmanicidal测定，所有化合物对的前鞭毛体阶段不活动L.恰加斯利什和L. braziliensis。
• Influence of the Chemical Structure on Odor Qualities and Odor Thresholds in Homologous Series of Alka-1,5-dien-3-ones, Alk-1-en-3-ones, Alka-1,5-dien-3-ols, and Alk-1-en-3-ols
  作者：Katja Lorber、Peter Schieberle、Andrea Buettner

  DOI：10.1021/jf404885j

  日期：2014.2.5

  Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.
• Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds
  作者：Akira Yanagisawa、Shigeki Habaue、Katsutaka Yasue、Hisashi Yamamoto

  DOI：10.1021/ja00093a010

  日期：1994.7

  The first direct preparation of allylbarium reagents by reaction of insitu generated reactive barium with various allylic chlorides and their new and unexpected selective allylation reactions with carbonyl compounds are disclosed. Highly reactive barium was readily prepared by the reduction of barium iodide with 2 equiv of lithium biphenylide in dry THF at room temperature. A variety of carbonyl compounds reacted with barium reagents generated from (E)- or (Z)-allylic chlorides in THF at -78 degrees C. All reactions resulted in high yields with remarkable alpha-selectivities not only with aldehydes but also with ketones. The double bond geometry of the starting allylic chloride was completely retained in each case. Stereochemically homogeneous (E)- and (Z)beta,gamma-unsaturated carboxylic acids were easily prepared in good yields by highly alpha-selective carboxylation of allylic barium reagents with carbon dioxide. A selective Michael addition reaction with alpha,beta-unsaturated cycloalkanone was also achieved using an allylbarium reagent. Treatment of 2-cyclopentenone (1 equiv) with allylbarium chloride (2 equiv) in THF at -78 degrees C for 20 min afforded 3-allylcyclopentanone in 94% yield with a 1,4/1,2 ratio of >99/1. Furthermore, the in situ generated barium enolate was efficiently trapped with various kinds of electrophiles (Me(2)C=CHCH2Br, (C5H11CHO)-C-n, and CH3COCl).
• Delaby; Lecomte, Bulletin de la Societe Chimique de France, 1937, vol. <5> 4, p. 1007,1011
  作者：Delaby、Lecomte

  DOI：——

  日期：——