1-氧杂螺[5.5]十一碳-2-烯-4-酮 | 62322-09-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 1-氧杂螺[5.5]十一碳-2-烯-4-酮
• 英文名称: 1-oxaspiro[5,5]undec-2-en-4-one
• 英文别名: 1-Oxaspiro[5.5]undec-2-en-4-one
• CAS: 62322-09-2
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ZXEKRGHNCVDXPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [4-(tert-Butyl-dimethyl-silanyloxy)-1-oxa-spiro[5.5]undec-3-en-2-yl]-dimethyl-amine 在 乙酰氯 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以65 mg的产率得到1-氧杂螺[5.5]十一碳-2-烯-4-酮
  参考文献：
  名称：

  未活化酮的氢键促进的杂-Diels-Alder反应

  摘要：

  我们报告了氢键促进异-Diels-Alder 反应加速的第一个例子，以及将这种催化用于简单的未活化酮的异-Diels-Alder 反应。使用该程序以良好的产率合成了几种螺稠合二氢吡喃。这种活化方案代表了传统路易斯酸催化的一种有吸引力且操作简单的替代方案。

  DOI：

  10.1021/ja0267627

文献信息

• Methods of performing cycloadditions, reaction mixtures, and methods of performing asymmetric catalytic reactions
  申请人：The University of Chicago

  公开号：US07230125B1

  公开（公告）日：2007-06-12

  Methods of performing cycloadditions are described that include (a) combining a first reactant and a second reactant in a hydrogen bonding solvent to form a reaction mixture; and (b) reacting the first reactant and the second reactant to form a cycloadduct. Methods of performing asymmetric catalytic reactions are also described that include (a) combining a first reactant, a second reactant, and a catalytic amount of a chiral hydrogen-bond donor in a solvent to form a reaction mixture; and (b) reacting the first reactant and the second reactant to form an enantiomeric excess of a reaction product. Reaction mixtures corresponding to these methods are also described.

  描述了进行环加成的方法，包括(a)在氢键合剂溶剂中将第一反应物和第二反应物组合以形成反应混合物；以及(b)使第一反应物和第二反应物发生反应以形成环加成物。还描述了进行不对称催化反应的方法，包括(a)在溶剂中将第一反应物、第二反应物和手性氢键供体的催化剂量组合以形成反应混合物；以及(b)使第一反应物和第二反应物发生反应以形成反应产物的对映体过量。还描述了与这些方法相对应的反应混合物。
• Studies towards the synthetic applicability of biocatalytic allylic oxidations with the lyophilisate of Pleurotus sapidus
  作者：Verena Weidmann、Serge Kliewer、Marko Sick、Sergej Bycinskij、Margarethe Kleczka、Julia Rehbein、Axel G. Griesbeck、Holger Zorn、Wolfgang Maison

  DOI：10.1016/j.molcatb.2015.07.008

  日期：2015.11

  The edible fungus Pleurotus sapidus (PSA) is a particularly interesting biocatalytic system for allylic oxidation and has a remarkably broad substrate range from terpenoids to fatty acids. The oxidations are most likely catalyzed by a lipoxygenase and involve the formation of peroxides via radical intermediates in the first rate-limiting step. We provide herein a rationalization of the observed regioselectivity of these conversions by means of computational determination of bond dissociation enthalpies of a set of tailor-made spirocyclic terpenoids. It was found that only strongly activated allylic positions (BDH298 of <80 kcal/mol) with neighboring heteroatoms or with activating alkyl groups are oxidized to the corresponding unsaturated lactones or enones, respectively. With the synthesis and purification of allylic hydroperoxide intermediates, we have been able to characterize the putative direct precursors of enones in PSA oxidations. Our results suggest a two-step oxidation mechanism involving hydroperoxide intermediates which are rapidly converted to the observed enones by an enzymatic reaction. (C) 2015 Elsevier B.V. All rights reserved.
• SADYKOV, T. S.;KOLXOSOVA, S. S.;ERZHANOV, K. B., IZV. AN KAZSSR. CEP. XIM.,(1988) N 2, 68-74
  作者：SADYKOV, T. S.、KOLXOSOVA, S. S.、ERZHANOV, K. B.

  DOI：——

  日期：——
• US7230125B1
  申请人：——

  公开号：US7230125B1

  公开（公告）日：2007-06-12
• US8513442B2
  申请人：——

  公开号：US8513442B2

  公开（公告）日：2013-08-20