2-Bromo-1-vinyl-2-cyclohexen-1-ol | 146355-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Bromo-1-vinyl-2-cyclohexen-1-ol
• 英文别名: 2-Bromo-1-ethenylcyclohex-2-en-1-ol
• CAS: 146355-23-9
• 化学式: C₈H₁₁BrO
• 分子量: 203.079
• InChiKey: BZSFJZLOGJOBEM-UHFFFAOYSA-N

物化性质

• 沸点：
  249.8±40.0 °C(Predicted)
• 密度：
  1.581±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Bromo-1-vinyl-2-cyclohexen-1-ol 在 重铬酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到2-Bromo-3-ethenylcyclohex-2-enone
  参考文献：
  名称：

  Conformational Biasing in 1,3-Oxidative Rearrangements of Dienols

  摘要：

  1-Vinyl-2-cycloalkenols are oxidized to form conjugated dienones in useful yields. Although this oxidative rearrangement is general, severe steric interactions can favor the formation of a conjugated dienal instead of a conjugated dienone. Several heterocyclic analogues were also studied.

  DOI：

  10.3987/com-07-s(w)62
• 作为产物：
  描述：

  2,3-dibromocyclohexanone 在 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 为溶剂， 反应 0.5h， 生成 2-Bromo-1-vinyl-2-cyclohexen-1-ol
  参考文献：
  名称：

  The Diene-Transmissive [4 + 2]-Cycloaddition Strategy: Stereoselective Synthesis of Advanced Intermediates to Quassinoids

  摘要：

  Complex intermediates to quassinoids', some optically active and containing many functional groups, were synthesized via a diene-transmissive Diels-Alder strategy. The stereochemistry of the key inter- and intramolecular cycloadditions was controlled by stereodefined groups on the preexisting C ring and on the tether.

  DOI：

  10.1021/jo00098a017

文献信息

• Intramolecularly Competitive Ireland-Claisen Rearrangements:  Scope and Potential Applications to Natural Product Synthesis
  作者：Sang-phyo Hong、Harriet A. Lindsay、Tripura Yaramasu、Xiaowei Zhang、Matthias C. McIntosh

  DOI：10.1021/jo010752r

  日期：2002.4.1

  A variety of bis-allylic esters were prepared by vinylmetal addition to cycloalkenones followed by esterification either in situ or in a separate operation. For chiral cyclohexenones, the vinyl additions generally occurred with > 10:1 diastereoselectivity. Although in some cases the bis-allylic esters proved to be sensitive to silica gel or other adsorbents, all of the esters examined could be isolated in acceptable purity. The Ireland-Claisen rearrangement of the bis-allylic esters occurred with complete regioselectivity via the exocyclic alkene. The alkene stereochemistry and the stereochemistry at C-2 and C-3 of the pentenoic acid products were consistent with a chairlike transition state in the rearrangement. Substituents at the carbons adjacent to the allylic carbinol carbon (i.e., C-2 or C-6 in cyclohexenone-derived substrates) directed the stereochemical course of the rearrangement. The rearrangements generally proceeded so as to place the larger of the C-2 or C-6 substituents in the pseudoequatorial position with respect to the chairlike transition state. For a bis-allylic ester bearing both a C-2-CH3 and a C-6-OMEM substituent, the rearrangement product resulted from the nominally smaller OMEM substituent occupying a pseudoequatorial position with respect to the chairlike transition state.
• A stereoselective diene-transmissive [4 + 2]-cycloaddition strategy for the construction of the tetracyclic quassinoid framework
  作者：Claude Spino、Gang Liu

  DOI：10.1021/jo00056a008

  日期：1993.2

  The tetracyclic quassinoid framework was stereoselectively constructed using a diene-transmissive Diels-Alder reaction between the cyclic formyl-diene 13 and ethyl vinyl ether.