4-carboethoxynona-1,8-dien-5-one | 142762-86-5

• 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-carboethoxynona-1,8-dien-5-one
• 英文别名: 2-allyl-3-oxo-hept-6-enoic acid ethyl ester；2-Allyl-3-oxo-hept-6-ensaeure-aethylester；6-Heptenoic acid, 3-oxo-2-(2-propenyl)-, ethyl ester；ethyl 3-oxo-2-prop-2-enylhept-6-enoate
• CAS: 142762-86-5
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: ZWFSTLNQRMSFCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-carboethoxynona-1,8-dien-5-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5-(ethynyl)nona-1,8-dien-5-ol
  参考文献：
  名称：

  The quest for planarizing distortions in hydrocarbons: two stereoisomeric [4.5.5.5]fenestranes

  摘要：

  According to semiempirical calculations the planarizing distortions in the central C(C)4 substructure of fenestranes, represented as 1, can be enhanced by a variety of structural modifications. Based on these results we selected the 7-hydroxy-c,c,c,c- and c,t,c,c[4.5.5.5]fenestranones 13 and 16 as precursors for the introduction of a bridgehead double bond. The efficient synthesis of these precursors and their chemical transformations are reported. Attempts to activate the hydroxyl group in 16 for introduction of a bridgehead double bond led to the rearrangement of the [4.5.5.5]fenestrane to a triquinacane skeleton. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.088
• 作为产物：
  描述：

  4-戊烯酸乙酯 在 sodium hydride 作用下， 以 甲苯 、 mineral oil 为溶剂， 反应 2.0h， 以67%的产率得到4-carboethoxynona-1,8-dien-5-one
  参考文献：
  名称：

  The quest for planarizing distortions in hydrocarbons: two stereoisomeric [4.5.5.5]fenestranes

  摘要：

  According to semiempirical calculations the planarizing distortions in the central C(C)4 substructure of fenestranes, represented as 1, can be enhanced by a variety of structural modifications. Based on these results we selected the 7-hydroxy-c,c,c,c- and c,t,c,c[4.5.5.5]fenestranones 13 and 16 as precursors for the introduction of a bridgehead double bond. The efficient synthesis of these precursors and their chemical transformations are reported. Attempts to activate the hydroxyl group in 16 for introduction of a bridgehead double bond led to the rearrangement of the [4.5.5.5]fenestrane to a triquinacane skeleton. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.088

文献信息

• Efficient synthesis of β-amino-α,β-unsaturated carbonyl compounds
  作者：Yuanhong Zhao、Jingfeng Zhao、Yongyun Zhou、Ze Lei、Liang Li、Hongbin Zhang

  DOI：10.1039/b419254k

  日期：——

  β-enaminones is presented: in the presence of tetraethyl orthosilicate, a number of highly functional β-enamino esters were obtained; this method provided an alternative for the formation of β-amino-α,β-unsaturated carbonyl compounds with mild and functional group compatible reaction conditions.

  提出了一种用于合成β-烯胺酯和β-烯酮的通用且高产的方法：在原硅酸四乙酯存在下，获得了许多高官能度的β-烯胺酯。该方法为形成具有温和且与官能团相容的反应条件的β-氨基-α，β-不饱和羰基化合物提供了另一种方法。
• Iodo cyclofunctionalization of 2,4-dialkenyl-1,3-dicarbonyl compounds: Synthesis of substituted 3-(2-furylidene)-2-furanones
  作者：Claudete J. Valduga、Hélio A. Stefani、Nicola Petragnani

  DOI：10.1002/jhet.5570390406

  日期：2002.7

  A facile method for the synthesis of substituted 3-(2-furylidene)-2-furanones has been developed using cyclofunctionalization reactions of 2,4-dialkenyl-1,3-dicarbonyl compounds and iodine as electrophile in the presence of Na2CO3, in refluxing chloroform. Compounds 4 are obtained in modest to good yields and their structural identification was established by 1H NMR, 1H COSY, 13C NMR and 1H-13C COSY

  在Na 2 CO 3存在下，利用2,4-二烯基-1,3-二羰基化合物和碘作为亲电子试剂的环官能化反应，已经开发了一种简便的合成取代的3-（2-呋喃基）-2-呋喃酮的方法。，在回流的氯仿中。以中等至良好的产率获得化合物4，并通过1 H NMR，1 H COSY，13 C NMR和1 H- 13 C COSY建立其结构鉴定。已经提出了一种使亚基呋喃酮的形成合理化的机制。
• Seleno and Telluro Cyclofunctionalization of α,γ-Diallyl-β-ketoesters: Polysubstituted Furan Derivatives
  作者：Hblio A. Stefani、Nicola Petragnani、Carlos A. Brandt、Daniela G. Rando、Claudtte J. Valduga

  DOI：10.1080/00397919908085985

  日期：1999.10

  Abstract Seleno- and telurocyclofunctionalized furan derivatives were prepared by reaction of phenylselenenyl bromide and p-methoxyphenyl tellurium trichloride with α,γ-diallyl-β-ketoesters in good yield.

  摘要 通过苯基硒基溴和对甲氧基苯基三氯化碲与α,γ-二烯丙基-β-酮酯反应，以良好的收率制备了硒基和远环官能化呋喃衍生物。
• Constituents of Pyrethrum Flowers. XXIV. Synthetic dl-cis-Cinerolone and Other Cyclopentenolones^1,2
  作者：Milton S. Schechter、Nathan Green、F. B. LaForge

  DOI：10.1021/ja01139a050

  日期：1952.10
• Iodine promoted cyclofunctionalization reaction of 2,4-dialkenyl-1,3-dicarbonyl compounds
  作者：Hélio A. Stefani、Nicola Petragnani、Claudéte J. Valduga、Carlos A. Brandt

  DOI：10.1016/s0040-4039(97)01079-4

  日期：1997.7

  The reactions of 2,4-dialkenyl-1,3-dicarbonyl compounds with I-2 lead to 5-iodoalkyl-4,5-dihydrofuran rings in good yield under mild conditions. (C) 1997 Elsevier Science Ltd.