1-氧杂螺[2.5]辛-4-烯 | 99495-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 中文名称: 1-氧杂螺[2.5]辛-4-烯
• 英文名称: 8-oxaspiro<5.2>oct-2-ene
• 英文别名: 1-Oxaspiro[2.5]oct-4-ene
• CAS: 99495-32-6
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: UZXHUZGASWCKEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-氧杂螺[2.5]辛-4-烯 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以64%的产率得到2-(hydroxymethyl)-1,3-cyclohexadiene
  参考文献：
  名称：

  Rigby, James H; Bazin, Berangere; Meyer, J Hoyt, Organic letters, 2002, vol. 4, # 5, p. 799 - 801

  摘要：

  DOI：
• 作为产物：
  描述：

  1-<(dimethylsulfonio)methyl>cyclohex-2-en-1-ol iodide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以91%的产率得到1-氧杂螺[2.5]辛-4-烯
  参考文献：
  名称：

  A convenient synthesis of vinyl spiro epoxides from .alpha.,.beta.-unsaturated ketones

  摘要：

  DOI：

  10.1021/jo00350a097

文献信息

• Strain-Promoted Oxidation of Methylenecyclopropane Derivatives using <i>N</i>-Hydroxyphthalimide and Molecular Oxygen in the Dark
  作者：T. E. Anderson、K. A. Woerpel

  DOI：10.1021/acs.orglett.0c02075

  日期：2020.7.17

  The hydroperoxidation of alkylidenecyclopropanes and other strained alkenes using an N-hydroxylamine and molecular oxygen occurred in the absence of catalyst, initiator, or light. The oxidation reaction proceeds through a radical pathway that is initiated by autoxidation of the alkene substrate. The hydroperoxides were converted to their corresponding alcohols and ketones under mild conditions.

  在不存在催化剂，引发剂或光的情况下，使用N-羟胺和分子氧对亚烷基亚环丙烷和其他应变烯烃进行加氢过氧化。氧化反应通过自由基途径进行，该自由基途径由烯烃底物的自氧化作用引发。在温和的条件下，氢过氧化物被转化为其相应的醇和酮。
• Insertions of Silylenes into Vinyl Epoxides: Diastereoselective Synthesis of Functionalized, Optically Active <i>trans</i>-Dioxasilacyclooctenes
  作者：Michel Prévost、K. A. Woerpel

  DOI：10.1021/ja906204a

  日期：2009.10.14

  communication describes a direct route to functionalized nonracemic trans-dioxasilacyclooctenes that involves stereoselective silylene insertions into vinyl epoxides to provide vinyl silaoxetane intermediates. These strained allylic silanes then undergo uncatalyzed allylation of aldehydes to afford trans-dioxasilacyclooctenes. Diastereoselective additions to these alkenes allow efficient transfer of planar

  该通讯描述了一种功能化非外消旋反式二氧杂硅杂环辛烯的直接途径，该途径涉及将立体选择性亚甲硅烷插入乙烯基环氧化物以提供乙烯基硅氧杂环丁烷中间体。这些应变的烯丙基硅烷然后进行醛的未催化烯丙基化，得到反式二氧硅杂环辛烯。这些烯烃的非对映选择性加成允许平面手性有效转移到立体碳原子处的手性。
• Strained organosilacyclic compounds: synthesis of anti-Bredt olefins and trans-dioxasilacyclooctenes
  作者：Michel Prévost、Joseph W. Ziller、K. A. Woerpel

  DOI：10.1039/c003227a

  日期：——

  Insertions of silylenes into the allylic carbon–oxygen bond of vinyl epoxides was shown to generate 1,2-silaoxetanes. These intermediates undergo highly diastereoselective additions to aldehydes to form anti-Bredt olefins and trans-dioxasilacyclooctenes. Additions of electrophiles could be performed selectively on the outside face of these strained trans-cycloalkenes to provide valuable functionalized compounds.

  将硅烯插入乙烯环氧化物的烯丙基碳-氧键生成1,2-硅氧烷。这些中间体经过高度非对映选择性的反应与醛发生加成，形成反-Bredt烯和反-二氧硅烷环辛烯。对这些受到张力的反环烷烃的外侧面选择性地进行亲电试剂的加成，可以得到有价值的功能化化合物。
• Furans in synthesis. 5. Furan-terminated cationic cyclizations in the preparation of fused, spirocyclic and bridged ring systems. An application to the synthesis of nakafuran 9
  作者：Steven P. Tanis、Paul M. Herrinton

  DOI：10.1021/jo00221a008

  日期：1985.10
• Zirconium-Promoted Epoxide Rearrangement−Alkynylation Sequence
  作者：Brian J. Albert、Kazunori Koide

  DOI：10.1021/jo702306k

  日期：2008.2.1

  [GRAPHICS]Additions of terminal alkynes to electrophiles are important transformations in organic chemistry. Generally, activated terminal alkynes react with epoxides in an S(N)2 fashion to form homopropargylic alcohols. We have developed a new synthetic method to form propargylic alcohols from epoxides and terminal alkynes via 1,2-shifts. This method involves cationic zirconium acetylides as both the activator of epoxides and nucleophiles. line to the mild conditions to pre-activate alkynes with silver nitrate, this synthetic method is useful for both electron-rich and electron-deficient alkynes with other acid- and base-sensitive functional groups.