N-methoxy-N-methyl-2-ethylhexanoylamide | 892393-82-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-methoxy-N-methyl-2-ethylhexanoylamide
• 英文别名: 2-ethyl-N-methoxy-N-methylhexanamide
• CAS: 892393-82-7
• 化学式: C₁₀H₂₁NO₂
• 分子量: 187.282
• InChiKey: NWBYLRTXCRACKB-UHFFFAOYSA-N

物化性质

• 沸点：
  226.3±23.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 N-methoxy-N-methyl-2-ethylhexanoylamide 以 四氢呋喃 为溶剂， 以63%的产率得到3-乙基-2-庚酮
  参考文献：
  名称：

  Ethyl-Branched Aldehydes, Ketones, and Diketones from Caimans (Caiman and Paleosuchus; Crocodylia, Reptilia)

  摘要：

  Secretions from the paracloacal glands of alligators (Alligator spp.) and caimans (Caiman spp., Melanosuchus niger, and Paleosuchus spp.) were examined by GC-MS. The secretions of the common caiman (C. crocodilus), the broadsnouted caiman (C. latirostris), the yacare caiman (C. yacare), the dwarf caiman (P. palpebrosus), and the smooth-fronted caiman (P. trigonatus) yielded a new family of 43 aliphatic carbonyl compounds that includes aldehydes, ketones, and beta-diketones with an ethyl branch adjacent to the carbonyl group. The identification of these glandular components and the syntheses and stereochemical investigations of selected compounds are described.

  DOI：

  10.1021/np0600797
• 作为产物：
  描述：

  2-乙基-己酸稀土盐 、 二甲羟胺盐酸盐 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 N-methoxy-N-methyl-2-ethylhexanoylamide
  参考文献：
  名称：

  雄性棕色大鼠的性吸引信息素：鉴定和野外实验

  摘要：

  诱捕棕色老鼠具有挑战性，因为它们避免了在栖息地中新近放置的陷阱。在此，我们报告了雄性棕色大鼠产生的性信息素的鉴定及其对野生雌性棕色大鼠陷阱捕获的影响。收集实验室保存的老鼠的尿液和粪便污染的被褥材料，比较未成年雄性和成年雄性以及成年雄性和雌性的被褥臭味，我们发现了九种特定于或最常见的化合物，性成熟成年男性的气味特征。当我们将这六种化合物的合成混合物（2-庚酮，4-庚酮，3-乙基-2-庚酮，2-辛酮，2-壬酮，4-壬酮）添加到两个成对的食物诱捕盒之一中时，这些盒子在实验室实验中吸引了更多的实验室应变雌性大鼠，并且在野外实验中捕获的野生雌鼠比相应的对照组多十倍。我们的数据表明信息素有助于捕获野生雌性棕色大鼠。

  DOI：

  10.1002/anie.201511864

文献信息

• A Weinreb amide approach to the synthesis of trifluoromethylketones
  作者：DiAndra M. Rudzinski、Christopher B. Kelly、Nicholas E. Leadbeater

  DOI：10.1039/c2cc35037h

  日期：——

  A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert–Prakash reagent (TMS–CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.

  报道了一条从Weinreb酰胺制备三氟甲基酮（TFMKs）的新路线。这是首次记录到Ruppert–Prakash试剂（TMS–CF3）以建设性方式与酰胺反应，并且可以无需担心过度三氟甲基化风险地合成TMFKs。
• Modular synthesis of tetra-substituted furans from alkynes, Weinreb amides, and aldehydes
  作者：Sajan Silwal、Ronald J. Rahaim

  DOI：10.1016/j.tetlet.2015.09.021

  日期：2015.10

  A method for the modular one-pot synthesis of tetra-substituted furans utilizing alkynes, Weinreb amides, and non-enolizable aldehydes has been developed. Under this titanium promoted method, furans were prepared in moderate yields with high levels of regioselectivity. The system showed good chemoselectivity tolerating aromatic and aliphatic bromides, chlorides, and fluorides, heteroaromatics, alkenes, and silyl ethers. (C) 2015 Elsevier Ltd. All rights reserved.
• Regioselective Synthesis of Enones via a Titanium-Promoted Coupling of Unsymmetrical Alkynes with Weinreb Amides
  作者：Sajan Silwal、Ronald J. Rahaim

  DOI：10.1021/jo5014417

  日期：2014.9.5

  A modular titanium-promoted coupling of unsymmetrical internal alkynes with Weinreb amides is described. The coupling reaction takes place at room temperature and affords E-trisubstituted enones in moderate to good yields with high levels of regioselectivity. The system shows moderate chemoselectivity.
• [EN] METHOD FOR MANUFACTURING KETONES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CÉTONES<br/>[JA] ケトンの製造方法
  申请人：JNC CORP

  公开号：WO2020017135A1

  公开（公告）日：2020-01-23

  雄のドブネズミ（Rattus norvegicus）の性フェロモンの成分であるケトンの製造方法を提供する。　以下の３つの段階からなる、ケトンの製造方法とする。 （１）アセトアルデヒドとブチルアルデヒドのアルドール縮合によりα，β－不飽和アルデヒドを得る第一段階； （２）第一段階で得られるα，β－不飽和アルデヒドの一つ以上とアルキル剤を反応させ、アリルアルコール類を得る第二段階； （３）第二段階で得られるアリルアルコール類をケトンへ異性化させる第三段階。
• Ethyl-Branched Aldehydes, Ketones, and Diketones from Caimans (<i>Caiman</i> and <i>Paleosuchus</i>; Crocodylia, Reptilia)
  作者：Karsten Krückert、Birte Flachsbarth、Stefan Schulz、Ute Hentschel、Paul J. Weldon

  DOI：10.1021/np0600797

  日期：2006.6.1

  Secretions from the paracloacal glands of alligators (Alligator spp.) and caimans (Caiman spp., Melanosuchus niger, and Paleosuchus spp.) were examined by GC-MS. The secretions of the common caiman (C. crocodilus), the broadsnouted caiman (C. latirostris), the yacare caiman (C. yacare), the dwarf caiman (P. palpebrosus), and the smooth-fronted caiman (P. trigonatus) yielded a new family of 43 aliphatic carbonyl compounds that includes aldehydes, ketones, and beta-diketones with an ethyl branch adjacent to the carbonyl group. The identification of these glandular components and the syntheses and stereochemical investigations of selected compounds are described.