ethyl 2-methyl-2-undecenoate | 113709-49-2

• 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 2-methyl-2-undecenoate
• 英文别名: (Z)-ethyl 2-methyldec-2-enoate；ethyl (Z)-2-methyl-2-decenoate；ethyl (Z)-2-methyldec-2-enoate
• CAS: 113709-49-2
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: WFAYJKFQVYWLPH-QXMHVHEDSA-N

物化性质

• 沸点：
  272.6±9.0 °C(Predicted)
• 密度：
  0.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  ethyl 2,3-epoxy-2-methyldecanoate 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 2-methyl-2-undecenoate 、 ethyl (R,S)-2-methyldec-2-enoate
  参考文献：
  名称：

  使用二氯化铬有效合成具有完全立体选择性的（E）-α，β-不饱和酮和酯

  摘要：

  （E）-α，β-不饱和酮1或酯2可以通过不同的2-氯-3-羟基酮3或酯4和CrCl 2的反应以完全的立体选择性获得。对CrCl 2或sa合成酮1的结果进行了比较研究。已经提出了解释两种β-消除反应的机制。

  DOI：

  10.1016/j.tet.2006.01.052

文献信息

• Scalable Preparation of Methylated Ando-Type Horner–Wadsworth–Emmons Reagent
  作者：Robert K. Bressin、Julia L. Driscoll、Yanping Wang、Kazunori Koide

  DOI：10.1021/acs.oprd.8b00423

  日期：2019.2.15

  commercially available Still–Gennari reagent. Ando developed an alternative reagent to achieve the same formation with less expensive reagents. However, an α-methylated Ando-HWE reagent has remained difficult to prepare, hindering a reliable route to α,β-disubstituted Z-enoates. Here, we report the development of a preparative synthesis of a methylated Ando-HWE reagent for the highly Z-selective HWE reaction

  Horner-Wadsworth-Emmons（HWE）反应对于复杂分子的化学合成至关重要，在醛或酮产生α，β-不饱和烯酸酯的过程中形成碳-碳双键。尽管经常使用，但醛中Z，立体选择性形成α，β-不饱和酯的方法主要限于使用市售的Still-Gennari试剂。安藤开发了另一种试剂，可以用较便宜的试剂实现相同的形成。然而，α-甲基化的Ando-HWE试剂仍然难以制备，这阻碍了获得α，β-二取代的Z-烯酸酯的可靠途径。在这里，我们报告了针对高Z的甲基化Ando-HWE试剂的制备合成方法的开发。-选择性HWE反应。合成成本为0.49美元/ mmol，比目前可购得的Still–Gennari试剂便宜得多（11美元/ mmol，Millipore Sigma 2018）。纯化过程不需要层析，只有重结晶是唯一的纯化方法，使其非常适合大规模生产。
• Highly <i>E</i>-Selective Solvent-Free Horner-Wadsworth-Emmons Reaction for the Synthesis of α-Methyl-α,β-Unsaturated Esters Using Either LiOH·H₂O or Ba(OH)₂·8H₂O
  作者：Kaori Ando、Wakana Isomura、Nariaki Uchida、Kanae Mori

  DOI：10.1246/bcsj.20220052

  日期：2022.6.15

  Horner-Wadsworth-Emmons reaction, which stirs a mixture of aldehyde, phosphonate reagent 1, and a base without solvent. The reaction of aromatic aldehydes and triethyl 2-phosphonopropionate 1a using LiOH·H2O gave 95-99% E-selectivity in 83-97% yield. The reaction of 1a with aliphatic aldehydes gave 92-94% E-selectivity except for α-branched aldehydes, and the selectivity was improved to 97-98% using ethyl 2-(diis

  ( E )-α-甲基-α,β-不饱和酯通过Horner-Wadsworth-Emmons 反应制备，该反应在无溶剂的情况下搅拌醛、膦酸酯试剂1和碱的混合物。芳香醛和 2-膦酰基丙酸三乙酯1a使用 LiOH·H 2 O 反应得到 95-99% E-选择性，产率为 83-97%。1a与脂肪醛的反应产生92-94% E-选择性，除了 α-支链醛，使用 2-(二异丙基膦酰基)丙酸乙酯1b将选择性提高到 97-98% 。使用 2-膦酰基丙酸三异丙酯1c改善了与 α-支链脂肪醛的反应和Ba(OH) 2 ·8H 2 O，得到98->99%的E-选择性和高产率。在THF中使用Ba(OH) 2 ·8H 2 O的HWE反应也以高产率高度选择性地得到( E )-α-甲基-α,β-不饱和酯。
• Synthesis of α,β-Disubstituted Acrylates via Galat Reaction
  作者：Tania Xavier、Sylvie Condon、Christophe Pichon、Erwan Le Gall、Marc Presset

  DOI：10.1021/acs.orglett.9b02291

  日期：2019.8.2

  Galat reactions between aldehydes and substituted malonic acids half oxyester were found to be efficiently catalyzed by morpholine in refluxing toluene. This transformation allows the stereoselective synthesis of diverse alpha,beta-disubstituted acrylates in moderate to good yields. This method constitutes an attractive alternative to existing methods in terms of scope and eco-compatibility.
• Solvent-free Horner–Wadsworth–Emmons reaction using DBU
  作者：Kaori Ando、Kyohei Yamada

  DOI：10.1016/j.tetlet.2010.04.072

  日期：2010.6

  The solvent-free Horner-Wadsworth-Emmons reaction with a variety of aldehydes using 1.5 equiv of DBU gave E-alpha,beta-unsaturated esters and ketones in high yields. The E-selectivity was high and the used DBU was recovered. (C) 2010 Elsevier Ltd. All rights reserved.
• Anionic versus photochemical diastereoselective deconjugation of diacetone d-glucose α,β-unsaturated esters
  作者：Frédéric Bargiggia、Olivier Piva

  DOI：10.1016/s0957-4166(03)00365-3

  日期：2003.7

  Deconjugation of diacetone D-glucose alpha, beta-unsaturated esters has been conducted by deprotonation using NaHMDS with HMPA as co-solvent followed by stereoselective protonation at low temperature. High selectivities (>95%) were obtained with oc-methyl linear compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.