(6,7)-epoxy-spiro[4,5]decane | 187-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (6,7)-epoxy-spiro[4,5]decane
• 英文别名: 7-oxaspiro[bicyclo[4.1.0]heptane-2,1'-cyclopentane]；6,7-Epoxy-spiro<4,5>decan；7-Oxaspiro[bicyclo[4.1.0]heptane-2,1'-cyclopentane]；spiro[7-oxabicyclo[4.1.0]heptane-2,1'-cyclopentane]
• CAS: 187-24-6
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: ITWRCBWVHHVKEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (6,7)-epoxy-spiro[4,5]decane 在 重铬酸吡啶 、 potassium tert-butylate 、 臭氧 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 25.17h， 生成 [7-(4-methoxyphenyl)-6-oxo-spiro[4.5]dec-7-yl]acetaldehyde
  参考文献：
  名称：

  Fragmentation of Nitrone Triflates to 9-Membered Rings

  摘要：

  A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

  DOI：

  10.1021/ol071049d
• 作为产物：
  描述：

  spiro[4,5]dec-6-ene 在 吡啶 、 双氧水 、 甲基三氧化铼(VII) 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(6,7)-epoxy-spiro[4,5]decane
  参考文献：
  名称：

  外消旋环氧化物对烯丙基醇的新型催化动力学拆分。

  摘要：

  研究了外消旋环氧化物通过催化对映选择性重排为烯丙基醇的动力学拆分。使用（1S，3R，4R）-3-（吡咯烷基）甲基-2-氮杂双环[2.2.1]庚烷1的锂盐作为催化剂，可以得到对映体富集形式的环氧化物和烯丙基醇。

  DOI：

  10.1021/ol025983e

文献信息

• Enantioselective Epoxidation of Nonconjugated <i>cis</i>-Olefins by Chiral Dioxirane
  作者：Christopher P. Burke、Yian Shi

  DOI：10.1021/ol901724v

  日期：2009.11.19

  A variety of nonconjugated cis-olefins has been enantioselectively epoxidized with chiral ketones 2, and up to 92% ee has been obtained. The two prochiral faces of an olefin are likely stereodifferentiated by the relative hydrophobicity of the olefin substituents and/or allylic oxygen functionality.

  多种非共轭顺式烯烃已与手性酮2对映选择性环氧化，获得了高达 92% 的 ee。烯烃的两个前手性面可能因烯烃取代基和/或烯丙基氧官能团的相对疏水性而立体分化。
• Novel Catalytic Kinetic Resolution of Racemic Epoxides to Allylic Alcohols
  作者：Arnaud Gayet、Sophie Bertilsson、Pher G. Andersson

  DOI：10.1021/ol025983e

  日期：2002.10.1

  [formula: see text] The kinetic resolution of racemic epoxides via catalytic enantioselective rearrangement to allylic alcohols was investigated. Using the Li-salt of (1S,3R,4R)-3-(pyrrolidinyl)methyl-2-azabicyclo [2.2.1] heptane 1 as catalyst allowed both epoxides and allylic alcohols to be obtained in an enantioenriched form.

  研究了外消旋环氧化物通过催化对映选择性重排为烯丙基醇的动力学拆分。使用（1S，3R，4R）-3-（吡咯烷基）甲基-2-氮杂双环[2.2.1]庚烷1的锂盐作为催化剂，可以得到对映体富集形式的环氧化物和烯丙基醇。
• Christol,H.; Vanel,R., Bulletin de la Societe Chimique de France, 1968, p. 1393 - 1398
  作者：Christol,H.、Vanel,R.

  DOI：——

  日期：——
• Kinetic resolution of racemic epoxides using a chiral diamine catalyst
  作者：Arnaud Gayet、Pher G. Andersson

  DOI：10.1016/j.tetlet.2005.05.017

  日期：2005.7

  The kinetic resolution of a variety of racemic epoxides has been performed using a chiral bicyclic diamine ligand. Using 5 mol% of catalyst very high selectivity could be achieved; both epoxide and the corresponding allylic alcohol could be obtained in up to 99% ee. (c) 2005 Elsevier Ltd. All rights reserved.
• Fragmentation of Nitrone Triflates to 9-Membered Rings
  作者：John A. Murphy、Mohan Mahesh、Gary McPheators、R. Vijaya Anand、Thomas M. McGuire、Robert Carling、Alan R. Kennedy

  DOI：10.1021/ol071049d

  日期：2007.8.1

  A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.