4-Methoxy-1-oxaspiro<5.5>undec-3-en-2-one | 1658-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-Methoxy-1-oxaspiro<5.5>undec-3-en-2-one
• 英文别名: 4-Methoxy-2-oxaspiro<5.5>undec-3-en-2-one；4-Methoxy-6-cyclohexanspiro-5.6-dihydro-2-pyron；4-Methoxy-6.6-pentamethylen-5,6-dihydro-2H-pyranon-(2)；4-methoxy-1-oxa-spiro[5.5]undec-3-en-2-one；4-Methoxy-1-oxa-spiro[5.5]undec-3-en-2-on；4-Methoxy-1-oxaspiro[5.5]undec-3-en-2-one
• CAS: 1658-21-5
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: BJFFUPMQMSGRJY-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  372.9±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  4-Methoxy-1-oxaspiro<5.5>undec-3-en-2-one 在 盐酸 、 乙醚 作用下， 生成 1-oxaspiro<5.5>undeca-2,4-dione
  参考文献：
  名称：

  717.关于生长素-a和生长素-b的化合物的研究。第二部分 生长素-b内酯类似物的制备

  摘要：

  DOI：

  10.1039/jr9500003628
• 作为产物：
  描述：

  在 水 作用下， 生成 4-Methoxy-1-oxaspiro<5.5>undec-3-en-2-one
  参考文献：
  名称：

  High threo diastereoselectivity via europium(III)-catalyzed cyclocondensation of a silyloxy diene with .alpha.-alkoxy aldehydes. Synthesis of (-)pestalotin

  摘要：

  DOI：

  10.1021/ja00327a054

文献信息

• Lichtempfindliches fotografisches Silberhalogenid-Aufzeichnungsmaterial
  申请人：Agfa-Gevaert AG

  公开号：EP0049449A1

  公开（公告）日：1982-04-14

  Das fotografische Silberhalogenid-Aufzeichnungsmaterial enthält in mindestens einer seiner lichtempfindlichen gelatinehaltigen Schichten ein die Carboxylgruppen der Gelatine aktivierendes Vernetzungsmittel aus der Gruppe der Carbamoylonium-, Carbamoylpyridinium- und Carbamoyloxypyridiniumsalze und eine als Aldehydentferner wirkende Dion-Verbindung der Formel in der Z für die zur Vervollständigung eines 5- oder 6-gliedrigen carbocyclischen oder heterocyclischen Ringes erforderlichen Atome steht, wobei als Heteroatome Sauerstoff, Stickstoff oder Schwefel enthalten sein können.

  感光卤化银记录材料至少在其中一个含感光明胶层中含有一种交联剂，该交联剂可活化明胶的羧基，该交联剂选自氨基甲酰基铵盐、氨基甲酰基吡啶鎓盐和氨基甲酰基氧基吡啶鎓盐以及二酮化合物组成的组，二酮化合物可作为除醛剂，其式为 其中 Z 代表完成 5 或 6 元碳环或杂环所需的原子，其中氧、氮或硫可作为杂原子存在。
• Reaction of Superoxide with Ascorbic Acid Derivatives: Insight into the Superoxide-Mediated Oxidation of Dehydroascorbic Acid
  作者：Aryeh A. Frimer、Pessia Gilinsky-Sharon

  DOI：10.1021/jo00114a031

  日期：1995.5

  In order to gain greater insight into the mechanism of superoxide-mediated oxidation of ascorbic acid (1) in aprotic media, we reacted O-2(.-) (generated from KO2/18-crown-6 in toluene) with vitamin C derivatives 13a and 14a and the corresponding mono- and dimethoxy analogs 13b and 13c, respectively. Dihydroxyfuranones 13a and 14a underwent oxidative cleavage with O-2(.-) yielding, upon methyl iodide workup, the corresponding keto ester (15 or 17, respectively) and threonic acid analog (16 or 18, respectively). On the other hand, mono- and dimethoxy analogs 13b and 13c each react with superoxide to give a single isolable product, oxyester 16 and alkylidenefuranone 20, respectively. Finally, 13a reacts with tert-butoxide, again yielding 16 as the major product. The data are best resolved by suggesting that ascorbic acid analogs 13a and 14a (and presumably ascorbic acid as well) are oxidized by O-2(.-) to the corresponding triketone 21 which reacts in turn by attack at the highly electrophilic central carbonyl C-2. Cyclization of the resulting 2-peroxy 1,3-diketone 22 into the C-1 carbonyl, followed by oxidative cleavage, saponification, and methylation, yields the observed products. By contrast, O-2(.-) oxidation of 13b and tert-butoxide oxidation of 13a yield 3-peroxy-1,2-diketone 29 which cyclizes into the C-1 carbonyl ultimately yielding 16. Finally, 13c, which lacks enolic hydrogens, undergoes abstraction of the gamma-hydrogen followed by the elimination of acetone, yielding 20. Similarly, 5,6-dihydropyrone 33 undergoes superoxide-mediated elimination yielding dienone 34. The data presented herein are consistent with the mechanism suggested by Sawyer et al. (J. Am. Chem. Sec. 1982, 104, 6273-6278) for the superoxide-mediated oxidation of dehydroascorbic acid (2)-with the modification that the position of initial O-2(.-) attack is at the C-2 (rather than the C-3) carbonyl.
• Polymer-supported electron-rich diene for hetero Diels–Alder reactions
  作者：Camille Pierres、Pascal George、Luc van Hijfte、Jean-Bernard Ducep、Marcel Hibert、André Mann

  DOI：10.1016/s0040-4039(03)00712-3

  日期：2003.4

  A Brassard diene analogue was grafted on a modified Merrifield resin and u sed in a hetero Diels-Alder reaction with various aldehydes or ketones. The reaction gave access to 6-substituted 5,6-dihydropyrones (5a-u). This new immobilized electron-rich diene is more stable than the corresponding native diene, and is a versatile supported reagent. (C) 2003 Elsevier Science Ltd. All rights reserved.
• A general synthesis of 5,6-dihydro-.alpha.-pyrones
  作者：R. W. Dugger、Clayton H. Heathcock

  DOI：10.1021/jo01295a002

  日期：1980.3
• US4418142A
  申请人：——

  公开号：US4418142A

  公开（公告）日：1983-11-29