(E)-3-hydroxy-2-((2E,6Z)-octa-2,6-dienylidene)cyclopentanone | 916484-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-hydroxy-2-((2E,6Z)-octa-2,6-dienylidene)cyclopentanone
• 英文别名: (2E)-3-hydroxy-2-[(2E,7Z)-nona-2,7-dienylidene]cyclopentan-1-one
• CAS: 916484-00-9
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: GNHXUYVRQQQIHR-UBHASBFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-hydroxy-2-((2E,6Z)-octa-2,6-dienylidene)cyclopentanone 在 三氟乙酸 作用下， 生成 2-((1E,6Z)-3-hydroxyocta-1,6-dienyl)cyclopent-2-enone
  参考文献：
  名称：

  Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides

  摘要：

  An unusual peroxide base-promoted isomerization is uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH2CL2 in a one-pot reaction. This methodology is applied to a convenient synthesis of dihydrojasmone. Moreover, functional groups placed on the side chain at C-6 participate in the base-catalyzed isomerizations via conjugate attack at the enone moiety to give 2-cyclopentenones carrying oxygen heterocycles at C-2. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.107
• 作为产物：
  描述：

  (1S,4R)-[(2E,7Z)-7-Nona-2,7-dien-(E)-ylidene]-2,3-dioxa-bicyclo[2.2.1]heptane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-hydroxy-2-((2E,6Z)-octa-2,6-dienylidene)cyclopentanone
  参考文献：
  名称：

  Unusual endoperoxide isomerizations: a convenient entry into 2-vinyl-2-cyclopentenones from saturated fulvene endoperoxides

  摘要：

  An unusual peroxide base-promoted isomerization is uncovered. Saturated endoperoxides derived from fulvenes give rise to 2-vinyl-2-cyclopentenones upon treatment with DBU in CH2CL2 in a one-pot reaction. This methodology is applied to a convenient synthesis of dihydrojasmone. Moreover, functional groups placed on the side chain at C-6 participate in the base-catalyzed isomerizations via conjugate attack at the enone moiety to give 2-cyclopentenones carrying oxygen heterocycles at C-2. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.107