抗-11-氧杂三环[4.3.1.12,5]十一碳-3-烯-10-酮 | 42768-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 抗-11-氧杂三环[4.3.1.12,5]十一碳-3-烯-10-酮
• 英文名称: (1α,2β,5β,6α)-11-oxatricyclo[4.3.1.1^2,5]undec-3-en-10-one
• 英文别名: anti-11-oxatricyclo<4.3.1.1^2,5>undec-3-en-10-one；anti-10-Oxatricyclo<4.3.1.1^2,5>undec-3-en-10-on；11-Oxatricyclo<4.3.1.1^2.5>undec-3-en-10-one；(1R,2R,5S,6S)-11-oxatricyclo[4.3.1.12,5]undec-3-en-10-one；11-oxatricyclo[4.3.1.12,5]undec-3-en-10-one
• CAS: 42768-72-9
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: ONSBKTHVMNVUEM-SPJNRGJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• 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

• 作为反应物：
  描述：

  抗-11-氧杂三环[4.3.1.12,5]十一碳-3-烯-10-酮 在 aluminum isopropoxide 作用下， 以 丙酮 、 xylene 为溶剂， 反应 12.0h， 以89%的产率得到anti-11-oxatricyclo<4.3.1.12,5>undec-3-en-anti-10-ol
  参考文献：
  名称：

  Camps, Pelayo; Castane, Joan; Feliz, Miguel, Chemische Berichte, 1989, vol. 122, p. 1313 - 1322

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯环己酮 在 水 、 magnesium sulfate 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 环己烷 为溶剂， 反应 23.0h， 生成 抗-11-氧杂三环[4.3.1.12,5]十一碳-3-烯-10-酮
  参考文献：
  名称：

  [4 + 3] CYCLOADDITION OF AMINOALLYL CATIONS WITH 1,3-DIENES: 11-OXATRICYCLO[4.3.1.12,5]UNDEC-3-EN-10-ONE

  摘要：

  DOI：

  10.15227/orgsyn.078.0212

文献信息

• α-Tosyloxyketones: Convenient [4+3] Cycloaddition Precursors
  作者：Scott T. Handy、Maurice Okello

  DOI：10.1055/s-2002-20474

  日期：——

  A concise, simple two-step method for the preparation of [4+3] cycloadducts from ketones using Koser"s reagent and trifluoroethanol-triethylamine has been developed. This sequence affords yields similar to those obtained using the α-halo and α-mesyloxyketones, but with the advantages of simplicity in preparation and stability of the intermediates.

  开发了一种简明、简便的两步法，用于从酮制备[4+3]环加成产物，采用Koser试剂和三氟乙醇-三乙胺体系。该序列提供的产率与使用α-卤代和α-甲磺酰氧基酮相当，但具有制备简便和中间体稳定性高的优点。
• Model Studies for the Preparation of Oxepanes and Fused Compounds by Tandem [4+3] Cycloaddition/Ring-Opening Metathesis/Cross Metathesis
  作者：Paolo Disetti、Linda Piras、Maria Moccia、Michele Saviano、Mauro F. A. Adamo

  DOI：10.1002/ejoc.201700994

  日期：2017.11.9

  Functionalised medium-sized ether rings were prepared in an efficient manner by [4+3] cycloaddition followed by ring-opening metathesis. This procedure provided medium-sized rings, which were shown to be useful for the assembly of fused bicyclic structures present in complex natural compounds. The potential of the chemistry described in this paper to be used in synthesis has been demonstrated by the

  通过 [4+3] 环加成和开环复分解以有效的方式制备功能化的中等大小的醚环。该过程提供了中等大小的环，这些环被证明可用于组装复杂天然化合物中存在的稠合双环结构。本文中描述的化学用于合成的潜力已通过功能化的大环醚和双环结构的制备得到证明。
• [4 + 3] Cycloadditions of cyclic oxyallyls and cyclic 1,3-dienes.
  作者：Shu-juan Jin、Jong-Ryoo Choi、Jonghoon Oh、Dongha Lee、Jin Kun Cha

  DOI：10.1021/ja00149a014

  日期：1995.11

  The [4 + 3] cycloaddition of the oxyallyl intermediates, derived from 2-chlorocyclohexanone and related compounds, to cyclic 1,3-dienes under the Fohlisch conditions (Et(3)N in CF3CH2OH) has been examined to assess its scope and limitations. Effects of substitution with alkyl or alkoxy groups on the cyclohexanone ring, along with variations of the base, solvent, or ring size have been investigated. Also included is a comparison between the Fohlisch cycloaddition and the Schmid cycloaddition (utilizing alpha'-chloroenamines). These reactions of cyclic oxyallyls afford tricyclic or tetracyclic cycloadducts of considerable molecular complexity with a well-defined stereochemical outcome and, thus, represent a new synthetic route to functionalized medium-sized carbocycles and heterocycles.
• Lithiumperchlorat/Triethylamin, ein neues Reagens zur Synthese von 3-Oxo-8-oxabicyclo[3.2.1] oct-6-enen aus α-Haloketonen und Furan
  作者：Rolf Herter、Baldur Föhlisch

  DOI：10.1055/s-1982-30033

  日期：——
• 4+3 Cycloaddition reactions of halogen-substituted cyclohexenyl oxyallylic cations
  作者：Michael Harmata、Lixin Shao、Laszlo Kürti、Asitha Abeywardane

  DOI：10.1016/s0040-4039(98)02629-x

  日期：1999.2

  2,6-Dibromo- and 2,2-dichlorocyclohexanone react with base in the presence of various dienes to give 4+3 cycloadducts in fair to good yields. Preliminary studies of the cycloadducts suggest that they are unstable and are recalcitrant to nucleophilic addition and cross-metathesis. However, the LAH reduction products undergo a quasi-Favorskii rearrangement upon treatment with potassium hydride and one cycloadduct derivative was dehalogenated using radical chemistry. (C) 1999 Elsevier Science Ltd. All rights reserved.