2-亚甲基-庚醛 | 4125-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-亚甲基-庚醛
• 中文别名: N-[5-[二(2-甲氧基乙基)氨基]-2-[(2-氯-4,6-二硝基苯基)偶氮]-4-(2-甲氧基乙氧基)苯基]乙酰胺
• 英文名称: 2-pentylacrolein
• 英文别名: 2-methyleneheptanal；2-formyl-1-heptene；2-Methyleneheptan-1-al；2-methylideneheptanal
• CAS: 4125-23-9
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: LDGVIXYITWDQFB-UHFFFAOYSA-N

物化性质

• 沸点：
  59 °C(Press: 13 Torr)
• 密度：
  0.8562 g/cm3(Temp: 14 °C)
• LogP：
  2.670 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2912190090

反应信息

• 作为反应物：
  描述：

  2-亚甲基-庚醛 在 乙酸酐 作用下， 生成 2-戊基-丙烯腈
  参考文献：
  名称：

  The Preparation of α-Alkylacrylonitriles

  摘要：

  DOI：

  10.1021/ja01168a011
• 作为产物：
  描述：

  1-Trimethylsiloxy-2-pentyl-cyclopropan 在 四甲基乙二胺 、 四氯化锡 作用下， 生成 2-亚甲基-庚醛
  参考文献：
  名称：

  .beta.-Trichlorostannyl ketones and aldehydes. Preparation and facile amine-induced dehydrostannation leading to .alpha.-methylene ketones and aldehydes

  摘要：

  Ring-opening reactions of siloxycyclopropanes 1 with SnCl4 take place under mild reaction conditions and site-selectively to give beta-trichlorostannyl ketones and aldehydes 3 in high yields. The beta-trichlorostannyl ketones and aldehydes thus obtained readily undergo base-induced dehydrotrichlorostannation at room temperature to give the corresponding alpha-methylene ketones and aldehydes 4. The reactions are quite general for amines, such as pyridine, triethylamine, N,N,N',N'-tetramethylethylenediamine (TMEDA), and 1,4-diazabicyclo[2.2.2]octane (DABCO), and the yields are good to high. One-pot conversion from siloxycyclopropanes 1 to alpha-methylene ketones or aldehydes 4 by consecutive treatment of 1 with SnCl4 and TMEDA is also successful. The H-1 NMR, C-13 NMR, Sn-119 NMR, and IR spectral properties of beta-stannyl ketones and aldehydes are also reported.

  DOI：

  10.1021/jo00027a008

文献信息

• Efficient α-Methylenation of Carbonyl Compounds in Ionic Liquids at Room Temperature
  作者：J. Rodrigues、Juliana Vale、Daniel Zanchetta、Paulo Moran

  DOI：10.1055/s-0028-1087389

  日期：——

  The application of several 1-butyl-3-methylimidazolium (BMIM) salt ionic liquids as solvent in the α-methylenation of carbonyl compounds at room temperature is reported. The ionic liquid [BMIM][NTf2] gave a clean reaction in a short time and good yields of several α-methylene carbonyl compounds. This ionic liquid was reused without affecting the reaction rates or yields over seven runs.

  报道了几种1-丁基-3-甲基咪唑鎓（BMIM）盐离子液体在常温下对羰基化合物进行α-亚甲基化的溶剂应用。离子液体[BMIM][NTf2]在短时间内提供了干净的反应和多种α-亚甲基羰基化合物的高产率。这种离子液体在连续七次使用中重复使用，未影响反应速率或产率。
• Copper-Catalyzed Enantioselective Henry Reaction of Enals and Subsequent Iodocyclization: Stereoselective Construction of Chiral Azatricyclic Frameworks
  作者：Yirong Zhou、Yuequan Zhu、Shaobai Yan、Yuefa Gong

  DOI：10.1002/anie.201305148

  日期：2013.9.23

  In the frame: A cascade sequence combining an asymmetric Henry reaction and a stereoselective intramolecular iodocyclization provides direct access to an enantioenriched tricyclic hexahydrochromeno[4,3‐b]pyrrole framework (see scheme). The Henry reaction is catalyzed by copper in the presence of L1.

  在框架中：级联序列结合了不对称的亨利反应和立体选择性的分子内碘环化作用，可直接进入对映体富集的三环六氢色素[4,3- b ]吡咯骨架（参见方案）。在L1存在下铜催化了亨利反应。
• Rh-Catalyzed [5+1] and [4+1] Cycloaddition Reactions of 1,4-Enyne Esters with CO: A Shortcut to Functionalized Resorcinols and Cyclopentenones
  作者：Takahide Fukuyama、Yuko Ohta、Célia Brancour、Kazusa Miyagawa、Ilhyong Ryu、Anne-Lise Dhimane、Louis Fensterbank、Max Malacria

  DOI：10.1002/chem.201200045

  日期：2012.6.4

  novel Rh‐catalyzed [n+1]‐type cycloadditions of 1,4‐enyne esters, which involve an acyloxy migration as a key step. The efficient preparation of functionalized resorcinols, including biaryl derivatives, from readily available 1,4‐enyne esters and CO was achieved by Rh‐catalyzed [5+1] cycloaddition accompanied by 1,2‐acyloxy migration. When enyne esters had an internal alkyne moiety, the reaction proceeded

  我们开发了新颖的1,4-烯炔酯的Rh催化[ n +1]型环加成反应，其中涉及酰氧基迁移是关键步骤。通过Rh催化的[5 + 1]环加成并伴有1,2-酰氧基迁移，可以从容易获得的1,4-烯炔酯和CO中有效制备功能化间苯二酚，包括联芳基衍生物。当烯炔酯具有一个内部炔烃部分时，该反应会通过[4 + 1]型环加成反应进行，涉及1，3-酰氧基迁移，从而生成环戊烯酮。
• Carbon-Carbon Bond Formation by the Use of Chloroiodomethane as a C₁Unit. III. A Convenient Synthesis of the Mannich Base from Enol Silyl Ether by a Combination of Chloroiodomethane and<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetramethylmethanediamine
  作者：Sotaro Miyano、Hiroshi Hokari、Harukichi Hashimoto

  DOI：10.1246/bcsj.55.534

  日期：1982.2

  a combination of chloroiodomethane (CH2ClI) and N,N,N′,N′-tetramethylmethanediamine (TMMD) in DMSO as the solvent at ambient temperature. The mechanism of the transformation is discussed on the basis of product analysis and 1H NMR spectral studies. The reagent system CH2ClI/TMMD also provides a convenient route to the Eschenmoser’s salt (Me2\overset+N=CH2,\overset−I).

  羰基化合物的曼尼希二甲氨基甲基化可方便地通过烯醇三甲基甲硅烷基醚通过氯碘甲烷 (CH2ClI) 和 N,N,N',N'-四甲基甲二胺 (TMMD) 在 DMSO 作为溶剂在环境温度下进行。在产物分析和 1 H NMR 光谱研究的基础上讨论了转化机制。试剂系统 CH2ClI/TMMD 还提供了一个方便的路线到 Eschenmoser 盐 (Me2\overset+N=CH2,\overset-I)。
• Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO
  作者：Célia Brancour、Takahide Fukuyama、Yuko Ohta、Ilhyong Ryu、Anne-Lise Dhimane、Louis Fensterbank、Max Malacria

  DOI：10.1039/c0cc00747a

  日期：——

  carbonylative cycloaddition reaction has been developed using a Rh complex as catalyst. This reaction can convert readily available 3-acyloxy-1,4-enynes and CO to a wide range of functionalized resorcinols in good yields. A mechanism involving Rh-catalyzed cyclocarbonylation of 3-acyloxy-1,4-enynes accompanied by a 1,2-acyloxy shift is proposed for the present [5+1] type cycloaddition reaction.

  使用Rh络合物作为催化剂，已经开发出新颖的[5 + 1]型羰基环加成反应。该反应可以良好的产率将容易获得的3-酰氧基-1，4-烯炔和CO转化为多种官能化的间苯二酚。对于本发明的[5 + 1]型环加成反应，提出了涉及Rh催化的3-酰氧基-1，4-烯炔的环羰基化并伴有1，2-酰氧基转移的机理。