4-oxo-octanoic acid butyl ester | 18688-70-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 4-oxo-octanoic acid butyl ester
• 英文别名: Octanoic acid, 4-oxo-, butyl ester；butyl 4-oxooctanoate
• CAS: 18688-70-5
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: KKBGDUHCGSAMPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(benzotriazol-1-yl)pent-1-yl methyl thioether 在 正丁基锂 、 硫酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 水 为溶剂， 反应 25.17h， 生成 4-oxo-octanoic acid butyl ester
  参考文献：
  名称：

  Syntheses of Dialkyl and Functionalized Ketones via 1-(Benzotriazol-1-yl)alkyl Methyl Thioethers

  摘要：

  Benzotriazol-1-ylmethyl methyl thioether (1), after easy deprotonation by BuLi, reacted with alkyl halides to afford 1-(benzotriazol-1-yl)alkyl methyl thioethers 2 in good yields. The utility of compounds 2 as alkanoyl anion equivalents was demonstrated by the reactions of their anions with alkyl halides, aldehydes, ketones, esters, and phenyl isocyanate: the products were readily hydrolyzed to alpha-functionalized ketones in dilute aqueous acid.

  DOI：

  10.1021/jo971389k

文献信息

• Synthesis ofcis andtrans Whisky and Cognac lactones by the regiocontrolled alkylation of 2-(trimethylsiloxy)furan
  作者：Charles W. Jefford、Adam W. Sledeski、John Boukouvalas

  DOI：10.1002/hlca.19890720625

  日期：1989.9.20

  The racemic cis- and trans-5-butyltetrahydro-4-methylfuran-2-ones ( = whisky lactones) and their higher homologues tetrahydro-4-methyl-5-pentylfuran-2-ones ( = cognac lactones) have been prepared in 2–3 steps from 2-(trimethylsiloxy)furan. Regioselective alkylation of the latter afforded the 5-butyl- and 5-pentylfuran-2(5H)-ones which served as precursors for the stereocontrolled construction of either

  外消旋的顺式和反式-5-丁基四氢-4-甲基呋喃-2-酮（=威士忌内酯）及其高级同系物四氢-4-甲基-5-戊基呋喃-2-酮（=白兰地内酯）已在2中制备。从2-（三甲基甲硅烷氧基）呋喃中–3步。后者的区域选择性烷基化提供了5-丁基-和5-戊基呋喃-2（5 H）-一，它们用作饮料内酯的任一非对映异构体的立体控制结构的前体。还描述了这些5-烷基呋喃-2（5H）-一的重氮甲烷加合物的结构和互变异构。
• Regioselective alkylation of 2-trimethylsiloxyfuran; direct access to 4-substituted but-2-en-4-olides
  作者：Charles W. Jefford、Adam W. Sledeski、John Boukouvalas

  DOI：10.1039/c39880000364

  日期：——

  Primary iodides alkylate 2-trimethylsiloxyfuran in the presence of a molar excess of silver trifluoroacetate to give the 4-alkylbut-2-en-4-olides in 55–81% yield; as an illustration of the method, the cytotoxic marine sponge constituent, 4-(methoxycarbonylmethyl)but-2-en-4-olide was prepared in 79% yield in one step.

  在摩尔过量的三氟乙酸银存在下，将碘化伯烷基化2-三甲基甲硅烷氧基呋喃，以55-81％的收率得到4-烷基丁-2-烯-4-醇化物；作为该方法的说明，一步制备了细胞毒性海洋海绵成分4-（甲氧基羰基甲基）but-2-en-4-olide。
• Addition of aldehydes and their equivalents to electron-deficient alkenes using N-hydroxyphthalimide (NHPI) as a polarity-reversal catalyst
  作者：Shinya Tsujimoto、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1016/s0040-4039(03)01375-3

  日期：2003.7

  Radical addition of aldehydes and masked aldehydes like 1,3-dioxolanes to electron-deficient alkenes was achieved by the use of catalytic amounts of BPO and N-hydroxyphthalimide (NHPI) as a polarity-reversal catalyst under mild conditions. Three-component radical coupling of 1,3-dioxolanes, maleates, and alkenes was performed in the presence of BPO and NHPI under similar conditions. (C) 2003 Elsevier Ltd. All rights reserved.
• JEFFORD, CHARLES W.;SLEDESKI, ADAM W.;BOUKOUVALAS, JOHN, HELV. CHIM. ACTA, 72,(1989) N, C. 1362-1370
  作者：JEFFORD, CHARLES W.、SLEDESKI, ADAM W.、BOUKOUVALAS, JOHN

  DOI：——

  日期：——
• JEFFORD, CHARLES W.;SLEDESKI, ADAM W.;BOUKOUVALAS, JOHN, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 5, 364-365
  作者：JEFFORD, CHARLES W.、SLEDESKI, ADAM W.、BOUKOUVALAS, JOHN

  DOI：——

  日期：——