norbornenone ethylene glycol ketal | 31444-18-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: norbornenone ethylene glycol ketal
• 英文别名: bicyclo[2.2.1]hept-5-en-2-one ethylene ketal；Norbornenone ethylene ketal；spiro[1,3-dioxolane-2,5'-bicyclo[2.2.1]hept-2-ene]
• CAS: 31444-18-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: ZGQKHLRNYPGNGI-UHFFFAOYSA-N

物化性质

• 沸点：
  228.6±40.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  norbornenone ethylene glycol ketal 在 palladium on activated charcoal 硫酸 、 三乙胺 、 间氯过氧苯甲酸 、 氘 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 23.58h， 生成 rac-(1R,2S,4S,5R,6S)-2-benzoylbicyclo[2.2.1]heptan-2-yl-5,6-d2 methanesulfonate
  参考文献：
  名称：

  Properties of .alpha.-keto cations. Facile generation under solvolytic conditions

  摘要：

  DOI：

  10.1021/ja00379a018
• 作为产物：
  描述：

  6-bromobicyclo<2.2.1>hept-5-en-2-one 在 ammonium hydroxide 、 lithium dimethylcuprate 、 水 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 norbornenone ethylene glycol ketal
  参考文献：
  名称：

  6-Substituted bicyclo[2.2.1]hept-5-en-2-one ketals

  摘要：

  DOI：

  10.1021/jo00272a033

文献信息

• Regioselective additions of electrophiles to olefins remotely perturbed. The carbonyl group as a homoconjugated electron donating substituent.
  作者：Pierre-Alain Carrupt、Pierre Vogel

  DOI：10.1016/s0040-4039(00)87396-7

  日期：1982.1

  Electrophiles attack preferentially at the C(5) position of 2-norborn-5-enone and 2-bicyclo[2.2.2]oct-5-enone whereas the C(6) position is preferred for 2-chloronorborn-5-ene-2-carbonitriles and 2-chlorobicyclo[2.2.2]oct-5-ene-2-carbonitriles.

  亲电试剂优先攻击2-norborn-5-enone和2-双环[2.2.2] oct-5-enone的C（5）位置，而C（6）位置更适合2-chloronorborn-5-ene- 2-腈和2-氯双环[2.2.2]辛-5-烯-2-腈。
• New synthesis of 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I (ABHxD-I), a potent metabotropic receptor agonist
  作者：Paola Conti、Alan P Kozikowski

  DOI：10.1016/s0040-4039(00)00588-8

  日期：2000.5

  A new versatile synthesis of racemic ABHxD-I, a potent mGluR agonist, is presented. The synthesis was achieved by means of a Wolff rearrangement, which converted a 3-diazobicyclo[2.2.1]heptan-2-one into a bicyclo[2.1.1]hexane derivative.

  提出了外消旋ABHxD-I（一种有效的mGluR激动剂）的新通用合成方法。该合成是通过Wolff重排而完成的，该重排将3-重氮双环[2.2.1]庚-2--2-酮转化为双环[2.1.1]己烷衍生物。
• Formation of 2,2-disubstituted 1,3-cyclopentanediones from ketals with 1,2-bis(trimethylsilyloxy)cyclobutene
  作者：Yong-Jin Wu、Dean W. Strickland、Tracy J. Jenkins、Pei-Ying Liu、D. Jean Burnell

  DOI：10.1139/v93-169

  日期：1993.9.1

  The direct formation of 2,2-disubstituted 1,3-cyclopentanedione compounds by a Lewis acid catalysed reaction with 1,2-bis(trimethylsilyloxy)cyclobutene proceeds in good to excellent yields with unhindered ketals, but steric hindrance reduces the yields considerably. A carbonyl group α or β to the ketal, or a carbon–carbon double bond α to the ketal, stops the reaction completely. Orthoesters do not give geminally acylated products in synthetically useful yields.

  通过路易斯酸催化的反应，使用1,2-双(三甲基硅氧基)环丁烯与没有受阻碍的缩酮，直接形成2,2-二取代的1,3-环戊二酮化合物，产率良好至优秀，但立体位阻显著降低了产率。位于缩酮α或β位置的羰基，或者与缩酮α位置相邻的碳-碳双键会完全停止反应。正酯不会以合成有用的产率产生双酰化产物。
• Pharmaceutical Compositions and Methods for Relieving Pain and Treating Central Nervous System Disorders
  申请人：Breining Scott R.

  公开号：US20080242693A1

  公开（公告）日：2008-10-02

  Patients susceptible to or suffering from disorders, such as central nervous system disorders, which are characterized by an alteration in normal neurotransmitter release, such as dopamine release (e.g., Parkinsonism, Parkinson's Disease, Tourette's Syndrome, attention deficient disorder, or schizophrenia), are treated by administering a compound of Formulas 1 or 2, as described herein. The compounds of Formulas 1 and 2 are also useful for treating pain, and treating drug addiction, nicotine addiction, and/or obesity. The compounds can exist as individual stereoisomers, racemic mixtures, diastereomers and the like.

  患有或易感染神经系统紊乱（例如帕金森氏症、多动症、注意力缺陷障碍、精神分裂症等）的患者，其特征为神经递质释放（例如多巴胺释放）的异常改变，可通过给予本文所述的1或2式化合物治疗。1和2式化合物也可用于治疗疼痛、药物成瘾、尼古丁成瘾和/或肥胖症。这些化合物可以存在为单一立体异构体、混合物、对映异构体等形式。
• PHARMACEUTICAL COMPOSITIONS AND METHODS FOR RELIEVING PAIN AND TREATING CENTRAL NERVOUS SYSTEM DISORDERS
  申请人：Breining Scott R.

  公开号：US20100152228A1

  公开（公告）日：2010-06-17

  Patients susceptible to or suffering from disorders, such as central nervous system disorders, which are characterized by an alteration in normal neurotransmitter release, such as dopamine release (e.g., Parkinsonism, Parkinson's Disease, Tourette's Syndrome, attention deficient disorder, or schizophrenia), are treated by administering a compound of Formulas 1 or 2, as described herein. The compounds of Formulas 1 and 2 are also useful for treating pain, and treating drug addiction, nicotine addiction, and/or obesity. The compounds can exist as individual stereoisomers, racemic mixtures, diastereomers and the like.

  对于易感或患有中枢神经系统疾病的患者，这些疾病的特点是神经递质释放的正常变化，例如多巴胺释放（例如帕金森病，托瑞特综合症，注意力缺陷障碍或精神分裂症），可以通过给予本文所述的1或2式化合物来治疗。1和2式化合物也可用于治疗疼痛，药物成瘾，尼古丁成瘾和/或肥胖症。这些化合物可以存在于单个立体异构体，混合物，对映异构体等形式。