Bicyclo [5.3.1]undec-10-en-9-one | 73274-32-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bicyclo [5.3.1]undec-10-en-9-one
• 英文别名: Bicyclo[5.3.1]undec-7-en-9-one；Bicyclo[5.3.1]undec-1(10)-en-9-one
• CAS: 73274-32-5
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: JEYZYDOGZUGGHY-UHFFFAOYSA-N

物化性质

• 沸点：
  100-102 °C(Press: 0.2 Torr)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Bicyclo [5.3.1]undec-10-en-9-one 在 硫酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 457.0h， 生成 ((8S,9S,17S,18S)-17,18-Dihydroxy-11-methoxycarbonylmethyl-dispiro[7.0.7.2]octadec-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  双环[5.3.1] undec-1（10）-en-9-one的光化学行为

  摘要：

  将双环[5.3.1] undec-1（10）-en-9-one进行光解共轭，得到双环[5.3.1] undec-1（2）-en-9-one，将其依次转化为相应的亚甲基双环[4.2.2]癸酮。光解产物的非挥发性部分显示为环丁烷型二聚衍生物的混合物。

  DOI：

  10.1039/p19810000560
• 作为产物：
  描述：

  (Z)-cyclooct-2-enone 在 硫酸 、 sodium ethanolate 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 17.0h， 生成 Bicyclo [5.3.1]undec-10-en-9-one
  参考文献：
  名称：

  双环[5.3.1] undec-1（10）-en-9-one的光化学行为

  摘要：

  将双环[5.3.1] undec-1（10）-en-9-one进行光解共轭，得到双环[5.3.1] undec-1（2）-en-9-one，将其依次转化为相应的亚甲基双环[4.2.2]癸酮。光解产物的非挥发性部分显示为环丁烷型二聚衍生物的混合物。

  DOI：

  10.1039/p19810000560

文献信息

• A convenient route to 1,3-cyclooctatetraenophanes
  作者：Ting-Zhong Wang、Leo A. Paquette

  DOI：10.1016/0040-4039(88)80011-x

  日期：1988.1

  cyclooctatetraenes, bridged with methylene groups in a previously unknown 1,3-manner, have been prepared in racemic form by a route involving ultimate disrotatory opening of a suitably constructed bicyclo[4.2.0]octatriene precursor.

  已经通过外消旋形式通过涉及适当构建的双环[4.2.0]八碳三烯前体的最终旋转开环的途径，以外消旋形式制备了三个以亚甲基桥连的亚甲基桥连的环辛酸酯。
• Is pseudorotation the operational pathway for bond shifting within [8]annulenes? Probe of planarization requirements by 1,3-annulation of the cyclooctatetraene ring. Kinetic analysis of racemization and 2-D NMR quantitation of .pi.-bond alternation and ring inversion as a function of polymethylene chain length
  作者：Leo A. Paquette、Ting Zhong Wang、Jihmei Luo、Charles E. Cottrell、Amy E. Clough、Larry B. Anderson

  DOI：10.1021/ja00157a038

  日期：1990.1
• Enones with strained double bonds. 4. Bicyclo[5.3.1]undecane system
  作者：Herbert O. House、Ronald F. Sieloff、Thomas V. Lee、Marvin B. DeTar

  DOI：10.1021/jo01298a012

  日期：1980.5
• Constructing Conformationally Constrained Macrobicyclic Musks
  作者：Philip Kraft、Riccardo Cadalbert

  DOI：10.1002/1521-3765(20010803)7:15<3254::aid-chem3254>3.0.co;2-#

  日期：2001.8.3

  To investigate the structure odor correlation of musks,(12R)-12-methyl-13-tridecanotide (1), a macrocyclic musk, and 13-tridecanolide. its non-musky demethyl analogue. were conformationally constrained by introduction of methylene bridges between C-3 and C-8 or C-9. These [7.5.1]- and [8.4.1]macrobicycles were synthesized starting from bicyclo[5.3.1]undec-8-en-9-one (3) and bicyclo[4.3.1]dec-7-en-8-one (8), respectively, by a sequence consisting of catalytic hydrogenation. a-alkylation with a TBS-protected (tert-butyldimethylsilyl) hydroxy halide., acid-catalyzed cyclization, oxidative cleavage of the formed enol ether double bond, and subsequent reduction of the carbonyl group via its tosylhydrazone. The compound (1R,6R,9R)-(+)-6-methyl-4-oxa-bicyclo[7.5.1]pentadecan-3-one (22) was found to possess the most pronounced musk odor, and this was rationalized by a superposition analysis with the polycyclic aromatic musk odorant (4S,7R)-Galaxolide (2). In its (1S,6R,9S)-(+)stereoisomer-23 as well as in (1S,6R, 10R)-(+)-6-methyl-4-oxabicyclo-[8.4.1]pentadecan-3-one (18) the (6R)-methyl group seems to hinder the interaction with the musk receptor, while the demethyl compounds 7 and 12 showed only very faint odors.
• Synthetic Studies Involving Bridgehead α,β-Unsaturated Ketones: Protocols for Regiocontrolled α-Methylation
  作者：Leo A. Paquette、Hui-Ling Wang、Zhuang Su

  DOI：10.1055/s-1998-2127

  日期：1998.8