5-(hydroxymethyl)-1,3-cyclohexanedione | 70150-65-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(hydroxymethyl)-1,3-cyclohexanedione
• 英文别名: 1,3-Cyclohexanedione, 5-(hydroxymethyl)-；5-(hydroxymethyl)cyclohexane-1,3-dione
• CAS: 70150-65-1
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: SCTDHKQILWZJEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(hydroxymethyl)-1,3-cyclohexanedione 在 吡啶 、 碳酸氢钠 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 52.0h， 生成 6-[4-(tert-butoxycarbonyl)piperazin-1-ylmethyl]-4,5,6,7-tetrahydrobenzo[b]furan-4-one
  参考文献：
  名称：

  Conformationally Constrained Butyrophenones with Affinity for Dopamine (D₁, D₂, D₄) and Serotonin (5-HT_2A, 5-HT_2B, 5-HT_2C) Receptors:  Synthesis of Aminomethylbenzo[b]furanones and Their Evaluation as Antipsychotics

  摘要：

  A series of novel conformationally restricted butyrophenones (6-aminomethyl-4,5,6,7-tetrahydrobenzo [b]furan-4-ones bearing 4-(6-fluorobenzisoxazolyl)piperidine, 4-(p-fluorobenzoyl)piperidine, 4-(o-methoxyphenyl)piperazine, 4-(2-pyridyl)piperazine, 4-(2-pyrimidinyl)piperazine, or linear butyro(or valero)phenone fragments) were prepared and evaluated as antipsychotic agents by in vitro assays for affinity for dopamine receptors (D-1, D-2, D-4) and serotonin receptors (5-HT2A, 5-HT2B, 5-HT2C), by neurochemical studies, and by in vivo assays for antipsychotic potential and the risk of inducing extrapyramidal side effects. Potency and selectivity depended mainly on the amine fragment connected to the cyclohexanone structure. Compounds 20b,, with a benzoylpiperidine moiety, and 20c, with a benzisoxazolyl fragment, were selective for 5-HT2A receptors. The in vitro and in vivo pharmacological profiles of N-[(4-oxo-4,5,6,7-tetrahydrobenzo[b] furan-6-yl)methyl]-4-(p-fluorobenzoyl)piperidine (20b, QF1003B) and N-[(4-oxo-4,5,6,7-tetrahydrobenzo [b] furan-6-yl)methyl] -4-(6-fluorobenzisoxazol-3-yl)piperidine (20c, QF1004B) suggest that they may be effective as antipsychotic (neuroleptic) drugs.

  DOI：

  10.1021/jm0009890
• 作为产物：
  描述：

  1,4-二氢-3,5-二甲氧基苯甲醇 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 5-(hydroxymethyl)-1,3-cyclohexanedione
  参考文献：
  名称：

  新型苯并呋喃酮衍生物的合成，结合亲和力和分子对接分析作为潜在的抗精神病药。

  摘要：

  精神分裂症的复杂病因促使研究人员开发氯氮平相关的多靶点策略来对抗其症状。在这里，我们描述了一系列新的6-氨基甲基苯并呋喃酮，旨在寻找对5-HT2和多巴胺受体具有平衡亲和力的新化学结构。通过对5-HT2A和D2受体的生物学和计算研究，我们确定了受体丝氨酸残基S3.36和S5.46是解释这些新化合物对这组受体的亲和力和选择性差异的分子关键。具体而言，这些化合物与这些关键残基建立一个或两个H键的能力似乎解释了它们亲和力的差异。此外，我们将化合物2（QF1004B）描述为阐明5-HT2C受体在介导抗精神病作用和代谢不良事件中的作用的工具。化合物16a（QF1018B）对D2和5-HT2A受体表现出中等至高亲和力，而5-HT2A / D2比可预测为非典型抗精神病药物。

  DOI：

  10.1021/jm800602w

文献信息

• 由5-(羟甲基)-1,3-环己二酮合成的树脂单体及其制备方法
  申请人：上海博栋化学科技有限公司

  公开号：CN112661769B

  公开（公告）日：2022-06-28

  本发明属于光刻胶树脂单体，公开了一种由5‑(羟甲基)‑1,3‑环己二酮合成的树脂单体，树脂单体的结构式如下：其中R1为连接键、烃基或杂烃基，R2为烃基；R3为氢原子、烃基或杂烃基。其制备方法为，5‑(羟甲基)‑1,3‑环己二酮Ⅰ与甲基丙烯酰氯或甲基丙烯酸类化合物经酯化反应得到中间体Ⅱ；所述中间体Ⅱ在酸催化条件下与羟基羧酸类化合物经缩醛反应得到树脂单体Ⅲ。本发明的中半缩醛结构与酯基结构相连，使形成的光刻胶具有良好临界尺寸均一性。
• An Improved Iodine-Catalyzed Aromatization Reaction and Its Application in the Synthesis of a Key Intermediate of Cannabidiol
  作者：Fuqiang Zhu、Jingshan Shen、Safomuddin Abduahadi、Emmanuel Mintah Bonku、Hongjian Qin、Abdullajon Odilov、Haji Akber Aisa

  DOI：10.1055/a-2301-2431

  日期：——

  In this study, the development of an improved process for the synthesis of a key cannabidiol intermediate, methyl olivetolate, is described. The process involves an improvement of the iodine-catalyzed aromatization of cyclohexanone using potassium persulfate as an oxidant. This approach enabled for the efficient synthesis of methyl olivetolate with a 90% yield and 99.84% HPLC purity on a 5 kg scale

  在这项研究中，描述了一种关键大麻二酚中间体橄榄醇甲酯合成改进工艺的开发。该工艺涉及使用过硫酸钾作为氧化剂改进碘催化的环己酮芳构化反应。该方法能够有效合成橄榄酸甲酯，在 5 kg 规模上产率达 90%，HPLC 纯度达 99.84%。此外，与已建立的方法相比，总共 19 种环己酮底物提供了更高的间二酚化合物产率 (71-92%) 。
• SUBSTITUTED CARBAZOLES AS INHIBITORS OF SPLA2
  申请人：ELI LILLY AND COMPANY

  公开号：EP1395554B1

  公开（公告）日：2007-02-14
• Conformationally Constrained Butyrophenones with Affinity for Dopamine (D₁, D₂, D₄) and Serotonin (5-HT_2A, 5-HT_2B, 5-HT_2C) Receptors:  Synthesis of Aminomethylbenzo[<i>b</i>]furanones and Their Evaluation as Antipsychotics
  作者：Enrique Raviña、Isabel Casariego、Christian F. Masaguer、José A. Fontenla、Gisela Y. Montenegro、María E. Rivas、M. Isabel Loza、Maria J. Enguix、Maria Villazon、M. Isabel Cadavid、Gian C. Demontis

  DOI：10.1021/jm0009890

  日期：2000.11.1

  A series of novel conformationally restricted butyrophenones (6-aminomethyl-4,5,6,7-tetrahydrobenzo [b]furan-4-ones bearing 4-(6-fluorobenzisoxazolyl)piperidine, 4-(p-fluorobenzoyl)piperidine, 4-(o-methoxyphenyl)piperazine, 4-(2-pyridyl)piperazine, 4-(2-pyrimidinyl)piperazine, or linear butyro(or valero)phenone fragments) were prepared and evaluated as antipsychotic agents by in vitro assays for affinity for dopamine receptors (D-1, D-2, D-4) and serotonin receptors (5-HT2A, 5-HT2B, 5-HT2C), by neurochemical studies, and by in vivo assays for antipsychotic potential and the risk of inducing extrapyramidal side effects. Potency and selectivity depended mainly on the amine fragment connected to the cyclohexanone structure. Compounds 20b,, with a benzoylpiperidine moiety, and 20c, with a benzisoxazolyl fragment, were selective for 5-HT2A receptors. The in vitro and in vivo pharmacological profiles of N-[(4-oxo-4,5,6,7-tetrahydrobenzo[b] furan-6-yl)methyl]-4-(p-fluorobenzoyl)piperidine (20b, QF1003B) and N-[(4-oxo-4,5,6,7-tetrahydrobenzo [b] furan-6-yl)methyl] -4-(6-fluorobenzisoxazol-3-yl)piperidine (20c, QF1004B) suggest that they may be effective as antipsychotic (neuroleptic) drugs.
• Synthesis, Binding Affinity, and Molecular Docking Analysis of New Benzofuranone Derivatives as Potential Antipsychotics
  作者：Reyes Aranda、Karen Villalba、Enrique Raviña、Christian F. Masaguer、José Brea、Filipe Areias、Eduardo Domínguez、Jana Selent、Laura López、Ferran Sanz、Manuel Pastor、María I. Loza

  DOI：10.1021/jm800602w

  日期：2008.10.9

  establish one or two H-bonds with these key residues appears to explain their difference in affinity. In addition, we describe compound 2 (QF1004B) as a tool to elucidate the role of 5-HT2C receptors in mediating antipsychotic effects and metabolic adverse events. The compound 16a (QF1018B) showed moderate to high affinities for D2 and 5-HT2A receptors, and a 5-HT2A/D2 ratio was predictive of an atypical antipsychotic

  精神分裂症的复杂病因促使研究人员开发氯氮平相关的多靶点策略来对抗其症状。在这里，我们描述了一系列新的6-氨基甲基苯并呋喃酮，旨在寻找对5-HT2和多巴胺受体具有平衡亲和力的新化学结构。通过对5-HT2A和D2受体的生物学和计算研究，我们确定了受体丝氨酸残基S3.36和S5.46是解释这些新化合物对这组受体的亲和力和选择性差异的分子关键。具体而言，这些化合物与这些关键残基建立一个或两个H键的能力似乎解释了它们亲和力的差异。此外，我们将化合物2（QF1004B）描述为阐明5-HT2C受体在介导抗精神病作用和代谢不良事件中的作用的工具。化合物16a（QF1018B）对D2和5-HT2A受体表现出中等至高亲和力，而5-HT2A / D2比可预测为非典型抗精神病药物。