4-methoxybicyclo<2.2.2>octan-2-one | 4893-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxybicyclo<2.2.2>octan-2-one
• 英文别名: 4-Methoxybicyclo[2,2,2]octan-2-one；4-Methoxybicyclo[2.2.2]octan-2-one；4-Methoxy-bicyclo<2.2.2>octan-2-on；4-Methoxybicyclo<2.2.2>octan-2-on；4-Methoxy-bicyclo<2.2.2>octanon
• CAS: 4893-16-7
• 化学式: C₉H₁₄O₂
• mdl: MFCD00101922
• 分子量: 154.209
• InChiKey: VTSMKORLCJUQOV-UHFFFAOYSA-N

物化性质

• 沸点：
  110-111 °C(Press: 15 Torr)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxybicyclo<2.2.2>octan-2-one 在 氢氧化钾 、 四氯化锡 、 一水合肼 、 乙酰氯 作用下， 以 二乙二醇 为溶剂， 反应 2.0h， 生成 1-氯双环[2.2.2]辛烷
  参考文献：
  名称：

  Bridged ring compounds. VIII. 1-Halobicyclo[2.2.-2]octanes

  摘要：

  DOI：

  10.1021/jo01277a008
• 作为产物：
  描述：

  4-hydroxybicyclo<2.2.2>octan-2-one 在 吡啶 、 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.7h， 生成 4-methoxybicyclo<2.2.2>octan-2-one
  参考文献：
  名称：

  Solvolyses of 3-oxo- and 3-methylenebicyclo[2.2.2]oct-1-yl triflates: through-bond interaction of a .beta.-carbonyl lone pair with a cationic p orbital

  摘要：

  The rates of solvolysis of 3,3-dimethyl-2-oxobicyclo[2.2.2]oct-1-yl triflate (1b), 2-methylenebicyclo[2.2.2]oct-1-yl-triflate (2b), 5,5-dimethyl-3-oxobicyclo[2.2.2]oct-1-yl triflate (3b), 3-oxobicyclo[2.2.2]oct-1-yl triflate (4b), 3-methylenebicyclo[2.2.2]oct-1-yl triflate (5b), 3,3-dimethylbicyclo[2.2.2]oct-1-yl triflate (6b), and bicyclo[2.2.2]oct-1-yl triflate (7b) have been determined in 80% ethanol at 25-degrees-C. The O-18- and deuterium-labeling studies exclude both carbonyl addition and the enolization processes in the solvolyses of 3b and 4b. The rate ratios 1b/6b and 2b/7b are 10(-9.1) and 10(-3.9), respectively, indicating that the oxo substituent at the C(2) position is more electron withdrawing than the methylene substituent at the same position. In contrast, the rate ratios 3b/6b and 5b/7b, 10(-2.3) and 10(-2.2), respectively, are comparable with each other. Moreover, the rate ratio 4b/5b is 2.3, suggesting that the 3-oxo substituent is less electron withdrawing than the 3-methylene substituent with respect to the cationic center. Evaluation of the inductive effect of the oxo substituent at the C(3) position by means of the reported rates of solvolysis of various 2-or 3-substituted and unsubstituted bicyclo[2.2.2]oct-1-yl p-nitrobenzenesulfonates (14, 13, and 15, respectively) indicates a rate enhancement of 10(3)-10(4) for 3b and 4b. This marked enhancement is interpreted as evidence of the stabilization of the 3-oxo carbocation by a through-bond interaction between the beta-carbonyl lone pair and the cationic p orbital. The m Y relationships and the formation of fragmentation products 11 (9%) and 12 (20%) in the methanolyses of 3-oxo compounds 3b and 4b, respectively, support the through-bond interaction.

  DOI：

  10.1021/jo00061a036

文献信息

• Polycyclophenylpyrrolidines, their compositions and use
  申请人：The Upjohn Company

  公开号：US04036977A1

  公开（公告）日：1977-07-19

  Compounds of the formula ##STR1## where R.sub.4 X is a polycyclocoupled group and R.sub.1 and R.sub.2 are H or simple hydrocarbon and R.sub.3 has the same value and additionally simple acyl, can be made by a variety of syntheses. They have hypolipedemic and antiatherosclerotic properties, and are useful in that field.

  式为##STR1##的化合物，其中R.sub.4 X是多环偶联基团，R.sub.1和R.sub.2为H或简单的碳氢化合物，R.sub.3具有相同的值并且另外是简单酰基，可以通过各种合成方法制备。它们具有降脂和抗动脉粥样硬化的特性，在该领域中是有用的。
• Design, synthesis, and SAR studies of novel polycyclic acids as potent and selective inhibitors of human 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD-1)
  作者：Xiang-Yang Ye、Stephanie Y. Chen、Akbar Nayeem、Rajasree Golla、Ramakrishna Seethala、Mengmeng Wang、Timothy Harper、Bogdan G. Sleczka、Yi-Xin Li、Bin He、Mark Kirby、David A. Gordon、Jeffrey A. Robl

  DOI：10.1016/j.bmcl.2011.09.055

  日期：2011.11

  Starting from high throughput screening hit 2-adamantyl acetic acid 3, a series of polycyclic acids have been designed and synthesized as novel, potent, and selective inhibitors of human 11β-HSD-1. Structure–activity relationships of two different regions of the chemotype (polycyclic ring and substituents on quaternary carbon) are discussed.

  从高通量筛选命中的2-金刚烷基乙酸3开始，已设计和合成了一系列多环酸，作为人类11β-HSD-1的新型，有效和选择性抑制剂。讨论了化学型的两个不同区域（多环和季碳上的取代基）的结构-活性关系。
• Polycycloanilines
  申请人：The Upjohn Company

  公开号：US04130561A1

  公开（公告）日：1978-12-19

  Compounds of the formula ##STR1## where R.sub.4 X is a polycyclocoupled group and R.sub.1 and R.sub.2 are H or simple hydrocarbon and R.sub.3 has the same value and additionally simple acyl, can be made by a variety of syntheses. They have hypolipedemic and antiatherosclerotic properties, and are useful in that field.

  公式为##STR1##的化合物，其中R.sub.4 X是多环偶合基团，R.sub.1和R.sub.2是H或简单的碳氢化合物，R.sub.3具有相同的价值并且还具有简单的酰基，可以通过各种合成方法制备。它们具有降低脂质和抗动脉粥样硬化的特性，在该领域中是有用的。
• US4036977A
  申请人：——

  公开号：US4036977A

  公开（公告）日：1977-07-19
• US4120899A
  申请人：——

  公开号：US4120899A

  公开（公告）日：1978-10-17