5-benzyloxymethyl-1,3-cyclohexanedione | 70150-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-benzyloxymethyl-1,3-cyclohexanedione
• 英文别名: 5-(benzyloxymethyl)cyclohexane-1,3-dione；5-(Phenylmethoxymethyl)cyclohexane-1,3-dione
• CAS: 70150-67-3
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: LEUIXOUNJRMEHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-benzyloxymethyl-1,3-cyclohexanedione 在 palladium diacetate 、 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 对甲苯磺酸 、 三乙胺 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 98.0h， 生成 2-(p-toluenesulfonyl)oxymethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
  参考文献：
  名称：

  Butyrophenone analogues in the carbazole series as potential atypical antipsychotics: synthesis and determination of affinities at D2, 5-HT2A, 5-HT2B and 5-HT2C receptors

  摘要：

  We describe practical and efficient routes for synthesis of 2-aminomethyl-1,2,3,9-tetrahydro-4H-carbazol-4-ones using the Fischer indole synthesis or palladium-catalysed cyclization methodologies, as well as their affinities for D-2, 5-HT2A and 5-HT2C receptors, and their activity at the 5-HT2B receptor. The most active compounds, 4b (QF 2003B) and 4c (QF 2004B), with a pK(i) (5-HT2A/D-2) ratio of 1.28 show a potential antipsychotic profile according to Meltzer's classification. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00109-4
• 作为产物：
  描述：

  1,4-二氢-3,5-二甲氧基苯甲醇 在 盐酸 、 sodium hydride 作用下， 以 水 为溶剂， 生成 5-benzyloxymethyl-1,3-cyclohexanedione
  参考文献：
  名称：

  [EN] ANTIMICROBIAL COMPOSITIONS, METHODS OF USE, AND METHODS OF TREATMENT OF INFECTIONS
  [FR] COMPOSITIONS ANTIMICROBIENNES, LEURS MÉTHODES D'UTILISATION, ET MÉTHODES DE TRAITEMENT D'INFECTIONS

  摘要：

  本公开提供包括化合物（例如，化合物A-D）的组合物、包括该化合物的药物组合物、治疗疾病或疾病的方法、使用组合物或药物组合物的治疗方法等。

  公开号：

  WO2016191412A1

文献信息

• Synthetic studies towards (±)-isopalhinine A: Preparation of the bicyclic core via Nazarov cyclization
  作者：Mina C. Nakhla、Christopher D. Cook、John L. Wood

  DOI：10.1016/j.tetlet.2021.153177

  日期：2021.6

  This manuscript describes progress towards the total synthesis of (±)-isopalhinine A wherein an allene ether Nazarov cyclization gives rise to the bicyclic core.

  这份手稿描述了 (±)-isopalhinine A 全合成的进展，其中丙二烯醚 Nazarov 环化产生了双环核心。
• Synthesis and binding affinity of potential atypical antipsychotics with the tetrahydroquinazolinone motif
  作者：Laura Carro、Enrique Raviña、Eduardo Domínguez、José Brea、María I. Loza、Christian F. Masaguer

  DOI：10.1016/j.bmcl.2009.09.041

  日期：2009.11

  A series of 8 new tetrahydroquinazolinone derivatives was synthesized and evaluated for binding affinity to D-2 and 5-HT2A human receptors; in addition, some properties related to blood-brain barrier penetration were calculated. From the results of these assays, three compounds were selected for further binding tests on D-1, D-3, and 5-HT2C human receptors, which are thought to be involved in schizophrenia. From these data, compound 19b emerged as the most promising candidate based on its good binding affinities for D-1, D-2, and D-3 receptors, high affinity for 5-HT2A, low affinity for 5-HT2C receptors, and a Meltzer's ratio characteristic of an atypical antipsychotic profile. (C) 2009 Elsevier Ltd. All rights reserved.
• New synthetic approaches to CNS drugs. A straightforward, efficient synthesis of tetrahydroindol-4-ones and tetrahydroquinolin-5-ones via palladium-catalyzed oxidation of hydroxyenaminones
  作者：Beatriz Pita、Christian F. Masaguer、Enrique Raviña

  DOI：10.1016/s0040-4039(02)01901-9

  日期：2002.10

  We have developed a facile and efficient synthesis of new conformationally restricted butyrophenones in the indole and quinoline series via palladium-catalyzed oxidation of hydroxyenaminones, and subsequent cyclization followed by spontaneous arornatization. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US9737509B1
  申请人：——

  公开号：US9737509B1

  公开（公告）日：2017-08-22