2-(m-Methoxybenzyl)-cyclohexanon | 31559-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(m-Methoxybenzyl)-cyclohexanon
• 英文别名: 2-[(3-methoxyphenyl)-methyl]cyclohexanone；2-(3-methoxy-benzyl)-cyclohexanone；2-[(3-methoxyphenyl)methyl]cyclohexan-1-one
• CAS: 31559-00-9
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: KFTYDTJYPQAGHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-(m-Methoxybenzyl)-cyclohexanon 在 盐酸 、 manganese(IV) oxide 、 sodium tetrahydroborate 、 正丁基锂 、 air 、 三乙基硼 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 9.25h， 生成 (E)-(3S,5R)-7-[2-(4-Fluoro-phenyl)-7-(3-methoxy-benzyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester
  参考文献：
  名称：

  HMG-CoA reductase inhibitors: design, synthesis, and biological activity of tetrahydroindazole-substituted 3,5-dihydroxy-6-heptenoic acid sodium salts

  摘要：

  Compounds comprising a series of 7-[2-(4-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-3,5-dihydroxy-6-heptenoic acid sodium salts (18) were synthesized and tested for their ability to inhibit HMG-CoA reductase in a partially purified enzyme preparation and cholesterol biosynthesis from acetate in cultured HEP-G2 cells. Changing the size of the saturated ring of the tetrahydroindazole nucleus did not improve potency, but incorporation of substituents at the 7-position resulted in up to 1700-fold improvement in inhibitory potency. Structure-activity studies revealed that the most potent compounds possess a substituted benzyl group at the 7-position, with a preference for steric bulk at the para position of the benzene ring. The most potent enzyme inhibitor (18t, IC50 = 3.0 nM) is approximately 3-fold more potent than lovastatin sodium salt (2). The most potent cholesterol biosynthesis inhibitor in HEP-G2 cells (18q, IC50 = 0.078 muM) is slightly less potent than 2 (sodium salt). Molecular modeling studies suggested that, when compared to the parent compound (18b) lacking the appropriate 7-substituent, 18t overlaps better with 2 and literature inhibitors 5 and 6 in a hydrophobic binding region adjacent to the enzyme active site.

  DOI：

  10.1021/jm00075a024
• 作为产物：
  描述：

  (E)-2-(3-methoxy-phenylmethylene)-cyclohexanol 以 正己烷 为溶剂， 生成 2-(m-Methoxybenzyl)-cyclohexanon
  参考文献：
  名称：

  取代基和溶剂极性对光化学[1,3]σ位移的影响。实验证据支持突发性事件的发生

  摘要：

  提供了有关在无环烯烃中突然极化的进一步实验证据。结果表明，分子内光化学[1,3] -OH的转变为1所生成的产物的产率仅取决于所用溶剂的极性。可以通过偶极溶剂分子的重新取向极化来稳定在辐射1时形成的两性离子中间体，从而很好地解释该结果。除此之外，发现在C 3 -C 9的末端碳原子处的烷基被取代。1中被苯基取代基形成的环外双键导致发生光化学[1,3] -H移位。取代基在环外双键上的这种指导作用可以在突然极化模型的基础上很好地解释。

  DOI：

  10.1016/s0040-4020(01)86197-4

文献信息

• SUBSTITUTED DIHYDRO AND TETRAHYDRO OXAZOLOPYRIMIDINONES, PREPARATION AND USE THEREOF
  申请人：CAO Bin

  公开号：US20100075994A1

  公开（公告）日：2010-03-25

  The present invention relates to a series of substituted dihydro and tetrahydro oxazolopyrimidinones, specifically, to a series of 2-substituted-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-ones and 2-substituted-2,3,5,6-tetra-hydro-oxazolo[3,2-a]pyrimidin-7-ones of formula (I): Wherein p, n, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.

  本发明涉及一系列取代二氢和四氢噁唑嘧啶酮，具体地说，涉及一系列式(I)的2-取代-2,3-二氢-噁唑并[3,2-a]嘧啶-7-酮和2-取代-2,3,5,6-四氢-噁唑并[3,2-a]嘧啶-7-酮： 其中p、n、X、Y、R1、R2、R3、R4、R5、R6、R7和R8如本文所定义。本发明还涉及制备这些化合物的方法，包括新颖的中间体。本发明的化合物是代谢型谷氨酸受体（mGluR）的调节剂，特别是mGluR2受体。因此，本发明的化合物在药物制剂中具有用途，特别是在治疗和/或预防各种中枢神经系统疾病（CNS）方面，包括但不限于急性和慢性神经退行性疾病、精神病、癫痫、焦虑、抑郁、偏头痛、疼痛、睡眠障碍和呕吐。
• 4,5-diaryloxazole derivatives
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US06025375A1

  公开（公告）日：2000-02-15

  Heterocyclic compounds of the formula: ##STR1## whereinR.sup.1 is carboxy or protected carboxy, R.sup.2 is aryl which may have suitable substituent(s), R.sup.3 is aryl which may have suitable substituent(s), A.sup.1 is lower alkylene, A.sup.2 is bond or lower alkylene and -Q- is ##STR2## etc., and pharmaceutically acceptable salts thereof which are useful as a medicament.

  式为：##STR1##其中R.sup.1是羧基或保护羧基，R.sup.2是芳基，可能有适当的取代基，R.sup.3是芳基，可能有适当的取代基，A.sup.1是较低的烷基，A.sup.2是键或较低的烷基，-Q-是##STR2##等，以及其药学上可接受的盐，可用作药物。
• Substituted dihydro and tetrahydro oxazolopyrimidinones, preparation and use thereof
  申请人：Cao Bin

  公开号：US08642603B2

  公开（公告）日：2014-02-04

  The present invention relates to a series of substituted dihydro and tetrahydro oxazolopyrimidinones, specifically, to a series of 2-substituted-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-ones and 2-substituted-2,3,5,6-tetra-hydro-oxazolo[3,2-a]pyrimidin-7-ones of formula (I): Wherein p, n, X, Y, R1, R2, R3, R4, R5, R6, R7 and R8 are as defined herein. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are modulators of metabotropic glutamate receptors (mGluR), particularly, mGluR2 receptor. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of central nervous system disorders (CNS), including but not limited to acute and chronic neurodegenerative conditions, psychoses, convulsions, anxiety, depression, migraine, pain, sleep disorders and emesis.

  本发明涉及一系列取代的二氢和四氢噁唑嘧啶酮，具体地说，涉及一系列式(I)的2-取代-2,3-二氢噁唑并[3,2-a]嘧啶-7-酮和2-取代-2,3,5,6-四氢噁唑并[3,2-a]嘧啶-7-酮，其中p，n，X，Y，R1，R2，R3，R4，R5，R6，R7和R8如本文所定义。本发明还涉及制备这些化合物的方法，包括新的中间体。本发明的化合物是代谢型谷氨酸受体（mGluR）的调节剂，特别是mGluR2受体。因此，本发明的化合物在制药领域中有用，特别是在治疗和/或预防各种中枢神经系统疾病（CNS）方面，包括但不限于急性和慢性神经退行性疾病、精神病、惊厥、焦虑、抑郁、偏头痛、疼痛、睡眠障碍和呕吐。
• [EN] COMPOUND HAVING CHIRAL SPIROBIINDANE SKELETON AND PREPARATION METHOD THEREFOR<br/>[FR] COMPOSÉ PRÉSENTANT UN SQUELETTE SPIROBIINDANE CHIRAL ET SON PROCÉDÉ DE PRÉPARATION<br/>[ZH] 手性螺二氢茚骨架化合物及其制备方法
  申请人：ZHEJIANG JIUZHOU PHARM CO LTD

  公开号：WO2017107789A1

  公开（公告）日：2017-06-29

  本发明公开了一种手性螺二氢茚骨架化合物及其制备方法。本发明的手性稠环螺二氢茚骨架化合物如式I或I'所示；本发明的手性螺二氢茚骨架化合物的制备方法，其包括如下步骤：溶剂中，催化剂作用下，将如式III所示的化合物进行分子内傅里德-克拉夫茨反应，制得如式I所示的化合物；所述催化剂为布朗斯特酸或路易斯酸。本发明的制备方法，不需采用手性起始原料或手性拆分试剂、无须进行手性拆分步骤、方法简单、后处理简便、经济环保、产物收率高、产物光学纯度和化学纯度高。采用本发明的手性稠环螺二氢茚骨架化合物制得的过渡金属催化的不对称反应的催化剂，催化效果显著，产物收率＞99％，产物ee值高达＞99％。
• Use of dicobalt hexacarbonyl-estabilized propargyl cations in intramolecular Friedel-Crafts alkylations
  作者：David D. Grove、Frank Miskevich、Chase C. Smith、James R. Corte

  DOI：10.1016/s0040-4039(00)97041-2

  日期：1990.1