Methyl 3-formylheptanoate | 152645-59-5

• 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 3-formylheptanoate
• CAS: 152645-59-5
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: YZQLQOXYIJJCSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基锂 、 Methyl 3-formylheptanoate 在 copper(l) iodide 作用下， 生成 (4R,5S)-4-butyl-5-methyldihydrofuran-2(3H)-one 、 (4R,5R)-4-butyldihydro-5-methyl-2(3H)-furanone
  参考文献：
  名称：

  Ester groups as effective ligands in chelate-controlled additions of cuprates and Grignard reagents to chiral .beta.-formyl esters to form .gamma.-lactones.

  摘要：

  Addition of cuprates to chiral methyl beta-formyl carboxylates 1a-1d provided gamma-lactones 2-7 in excellent trans-selectivity. The high diastereofacial selectivity was only obtained employing diethyl ether as solvent while tetrahydrofuran gave inferior results. Similar solvent effects were observed in the additions of various Grignard reagents to 1a, which afforded gamma-lactones 2,3,12, and 13 in moderate trans-selectivity. The best solvent for these reactions was dichloromethane. The 1,3-induction of cuprate additions was studied by using aldehydes 8a-8c. The results obtained were interpreted in terms of chelate-controlled additions with formation of seven-membered ring chelates which involve both carbonyl functions of aldehyde 1 or 8. The function of ester groups as effective ligands of lithium or MgX cations may also be of importance for other stereoselective reactions employing organometallic reagents.

  DOI：

  10.1021/jo00075a022
• 作为产物：
  描述：

  丁基环氧乙烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 氘代乙腈 为溶剂， 反应 17.25h， 生成 Methyl 3-formylheptanoate
  参考文献：
  名称：

  来自末端环氧化物和受阻锂酰胺的烯胺

  摘要：

  氨基锂与环氧化物的新反应模式导致受阻烯胺。描述了这些烯胺中的一些与未活化的伯和仲烷基卤化物的反应，这扩大了可用于合成单烷基化醛的亲电子试剂的范围。

  DOI：

  10.1021/ja031770o

文献信息

• Synthesis and <i>C</i>-Alkylation of Hindered Aldehyde Enamines
  作者：David M. Hodgson、Christopher D. Bray、Nicholas D. Kindon、Nigel J. Reynolds、Steven J. Coote、Joann M. Um、K. N. Houk

  DOI：10.1021/jo802016t

  日期：2009.2.6

  hindered lithium amides with terminal epoxides is described whereby aldehyde enamines are produced via a previously unrecognized reaction pathway. Some of these aldehyde enamines display unprecedented C-alkylation reactivity toward unactivated primary and secondary alkyl halides. For comparison, the reactivity of aldehyde enamines synthesized via a traditional condensation method was examined. C- rather

  描述了一种新的受阻锂酰胺与末端环氧化物的反应模式，其中醛烯胺是通过以前无法识别的反应途径生成的。这些醛烯胺中的一些对未活化的伯和仲烷基卤显示出前所未有的C-烷基化反应性。为了比较，检查了通过传统缩合方法合成的醛烯胺的反应性。在一系列亲电试剂中，C-而不是N-烷基化是主要的反应途径，这使得从α-烷基化的醛到合成烷基的途径比以前报道的更有用。
• ASYMMETRIC SYNTHESIS OF 3-ALKYLSUCCINALDEHYDIC ACID METHYL ESTERS
  作者：Masatoshi Asami、Teruaki Mukaiyama

  DOI：10.1246/cl.1979.569

  日期：1979.5.5

  The highly stereoselective Michael addition was achieved by treating an aminal, prepared from (S)-2-(anilinomethyl)pyrrolidine and fumaraldehydic acid methyl ester, with the Grignard reagents. 3-Alkylsuccinaldehydic acid methyl esters were obtained with high enantiomeric excesses by the hydrolysis of the resulting aminals.

  高度立体选择性迈克尔加成是通过用格氏试剂处理由（S）-2-（苯胺基甲基）吡咯烷和富马醛酸甲酯制备的胺醛实现的。3-烷基琥珀醛酸甲酯是通过水解所得缩醛胺获得的，对映体过量。
• Asymmetric Synthesis of α-Alkylated Aldehydes using Terminal Epoxide-Derived Chiral Enamines
  作者：David M. Hodgson、Naeem S. Kaka

  DOI：10.1002/anie.200804369

  日期：2008.12.8