5-acetyl-2-methyl-2-cyclohexen-1-one | 924824-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetyl-2-methyl-2-cyclohexen-1-one
• 英文别名: (5RS)-5-acetyl-2-methylcyclohex-2-en-1-one；5-Acetyl-2-methylcyclohex-2-en-1-one
• CAS: 924824-39-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: HIFCQOWCDQXRJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-acetyl-2-methyl-2-cyclohexen-1-one 生成 4-(4-Oxocyclohexyl)phenyl acetate
  参考文献：
  名称：

  Bicyclic peroxides compositions for and treatment of malaria therewith

  摘要：

  这个句子的中文翻译如下：新型4-取代的4,8-二甲基-2,3-二氧杂双环[3.3.1]壬烷-7-酮，对疟疾病原体具有显著的活性，可用于预防和控制疟疾。

  公开号：

  US04977184A1
• 作为产物：
  描述：

  5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 在 sodium periodate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以82%的产率得到5-acetyl-2-methyl-2-cyclohexen-1-one
  参考文献：
  名称：

  Detection of a “Nonaromatic” NIH Shift during In Vivo Metabolism of the Monoterpene Carvone in Humans

  摘要：

  High-resolution gas chromatography in combination with mass spectrometry and high-resolution mass spectrometry was used to determine the positions and extent of labeling in the metabolites of carvone, namely in alpha,4-dimethyl-5-oxo-3-cyclohexene-1-acetic acid (dihydrocarvonic acid), (alpha-methylene-4methyl-5-oxo-3-cyclohexene-1 -acetic acid (carvonic acid), and 5-(1,2-dihydroxy-l-methylethyl)-2methyl-2-cyclohexen-1 -one (uroterpenolone), after human ingestion of 9,9-dideutero- and 9-(13)-C-carvone. Carvonic acid was formed by oxidation at the methyl carbon of the isopropenyl group of carvone, whereas dihydrocarvonic acid was formed by oxidation at the methylene position, most probably via carvone epoxide. A "nonaromatic" NIH shift must occur during the subsequent reactions yielding dihydrocarvonic acid. Additionally, dehydrogenation of dihydrocarvonic acid and hydrogenation of carvonic acid were observed, resulting in minor amounts of both acids owning a carboxy group of opposite origin. Uroterpenolone was found to be exclusively formed by oxidation at the methylene carbon of the isopropenyl group of carvone, and thus, most probably by hydrolysis of carvone epoxide.

  DOI：

  10.1021/jf011199h

文献信息

• POLYCYCLIC CARBOGENIC MOLECULES AND USES THEREOF AS ANTI-CANCER AGENTS
  申请人：Northwestern University

  公开号：US20190127306A1

  公开（公告）日：2019-05-02

  Disclosed are new polycyclic carbogenic molecules and their methods of synthesis. The new polycyclic carbogenic molecules may be utilized in anti-cancer therapies. In particular, the polycyclic carbogenic molecules may be formulated as pharmaceutical compositions that comprise the small molecules, which compositions may be administered in methods of treating and/or preventing cell proliferative diseases and disorders such as cancer. The new polycyclic carbogenic molecules may be prepared from vinyl- or allyl-substituted cyclohexenone precursors via preparation of a silyl bis-enol ether intermediate.

  揭示了新的多环碳基分子及其合成方法。这些新的多环碳基分子可以用于抗癌疗法。特别是，这些多环碳基分子可以制成包含小分子的药物组合物，这些组合物可以在治疗和/或预防细胞增殖性疾病和癌症等疾病的方法中使用。这些新的多环碳基分子可以通过从乙烯或烯丙基取代的环己酮前体制备硅烷双烯醚中间体来制备。
• Oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl) methanol with pyridinium chlorochromate
  作者：S. A. Torosyan、F. A. Gimalova、R. F. Valeev、M. S. Miftakhov

  DOI：10.1134/s1070428011050058

  日期：2011.5

  The oxidation of (1S,5R,7R,S)-(4,7-dimethyl-6-oxabicyclo[3.2.1]oct-3-en-7-yl)methanol epimeric at the C7 atom resulted in scalemic (5R)-5-acetyl-2-methylcyclohex-2-en-1-one.

  （1 S，5 R，7 R，S）-（4,7-二甲基-6-氧杂双环[3.2.1] oct-3-en-7-yl）甲醇差向异构体在C 7原子上的氧化导致（5 R）-5-乙酰基-2-甲基环己基-2-烯-1-酮。
• Bicyclic peroxides compositions for and treatment of malaria therewith
  申请人：Hoffmann-La Roche Inc.

  公开号：US04977184A1

  公开（公告）日：1990-12-11

  Novel 4-substituted-4,8-dimethyl-2,3-dioxabicyclo[3.3.1] nonan-7-ones which have a pronounced activity against the causative organism of malaria and can be used for the prevention and control of malaria.

  这个句子的中文翻译如下：新型4-取代的4,8-二甲基-2,3-二氧杂双环[3.3.1]壬烷-7-酮，对疟疾病原体具有显著的活性，可用于预防和控制疟疾。
• Detection of a “Nonaromatic” NIH Shift during In Vivo Metabolism of the Monoterpene Carvone in Humans
  作者：Wolfgang Engel

  DOI：10.1021/jf011199h

  日期：2002.3.1

  High-resolution gas chromatography in combination with mass spectrometry and high-resolution mass spectrometry was used to determine the positions and extent of labeling in the metabolites of carvone, namely in alpha,4-dimethyl-5-oxo-3-cyclohexene-1-acetic acid (dihydrocarvonic acid), (alpha-methylene-4methyl-5-oxo-3-cyclohexene-1 -acetic acid (carvonic acid), and 5-(1,2-dihydroxy-l-methylethyl)-2methyl-2-cyclohexen-1 -one (uroterpenolone), after human ingestion of 9,9-dideutero- and 9-(13)-C-carvone. Carvonic acid was formed by oxidation at the methyl carbon of the isopropenyl group of carvone, whereas dihydrocarvonic acid was formed by oxidation at the methylene position, most probably via carvone epoxide. A "nonaromatic" NIH shift must occur during the subsequent reactions yielding dihydrocarvonic acid. Additionally, dehydrogenation of dihydrocarvonic acid and hydrogenation of carvonic acid were observed, resulting in minor amounts of both acids owning a carboxy group of opposite origin. Uroterpenolone was found to be exclusively formed by oxidation at the methylene carbon of the isopropenyl group of carvone, and thus, most probably by hydrolysis of carvone epoxide.