spiro-1-one hydrochloride | 75930-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: spiro-1-one hydrochloride
• 英文别名: spiro[isochroman-3,4’-piperidin]-1-one hydrochloride；spiro[isochroman-3,4'-piperidine]-1-one hydrochloride；spiro[isochroman-3,4'-piperidin]-1-one hydrochloride；Spiro[isochromane-3,4'-piperidine]-1-one hydrochloride；spiro[4H-isochromene-3,4'-piperidine]-1-one;hydrochloride
• CAS: 75930-41-5
• 化学式: C₁₃H₁₅NO₂*ClH
• 分子量: 253.729
• InChiKey: BENYHUNHQCUDFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  294-304 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  spiro-1-one hydrochloride 在 硫酸 、 potassium nitrate 作用下， 反应 1.0h， 生成 7-Nitrospiro[isochromane-3,4'-piperidin]-1-one
  参考文献：
  名称：

  [EN] NOVEL SPIROLACTONE COMPOUNDS
  [FR] NOUVEAUX COMPOSÉS SPIROLACTONES

  摘要：

  本文提供的Formula（I）的螺内酯化合物可用作ACC1和/或ACC2的抑制剂。本文描述的螺内酯化合物可用于治疗与异常ACC1和/或ACC2活性相关的疾病或疾病，例如非酒精性脂肪性肝炎（NASH）、痤疮、肥胖症、糖尿病和癌症。本文还提供了包含Formula I的螺内酯化合物或其药用盐的药物组合物。

  公开号：

  WO2019006324A1
• 作为产物：
  描述：

  1'-benzyl-spiro[isochroman-3,4'-piperidin]-1-one 在 盐酸 、 palladium 10% on activated carbon 、 水 、 氢气 作用下， 以 乙醇 为溶剂， 以38%的产率得到spiro-1-one hydrochloride
  参考文献：
  名称：

  Novel spiropiperidine-based stearoyl-CoA desaturase-1 inhibitors: Identification of 1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-5-(trifluoromethyl)-3,4-dihydrospiro[chromene-2,4′-piperidine]

  摘要：

  Cyclization of the benzoylpiperidine in lead compound 2 generated a series of novel and highly potent spiropiperidine-based stearoyl-CoA desaturase (SCD)-1 inhibitors. Among them, 1'-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-5-(trifluoromethyl)-3,4-dihydrospiro[chromene-2,4'-piperidine] (19) demonstrated the most powerful inhibitory activity against SCD-1, not only in vitro but also in vivo (C57BL/6 J mice). With regard to the pharmacological evaluation, 19 showed powerful reduction of the desaturation index in the plasma of C57BL/6 J mice on a non-fat diet after a 7-day oral administration (q.d.) without causing notable abnormalities in the eyes or skin up to the highest dose (3 mg/kg) in our preliminary analysis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.043

文献信息

• Synthesis and structure-activity relationship of spiro[isochromanpiperidine] analogs for inhibition of histamine release. 1
  作者：Masatoshi Yamato、Kuniko Hashigaki、Masao Ikeda、Hidetoshi Ohtake、Kenji Tasaka

  DOI：10.1021/jm00134a013

  日期：1981.2

  ,4'-piperidines] were prepared and examined for their biological activity. Several of the compounds inhibited the compound 48/80 induced histamine release from isolated rat peritoneal mast cells. The structural requirements for this activity in the present series are discussed.

  制备了两种类型的1'-烷基螺基[isochroman-3,4-哌啶]和1'-烷基螺基[isochroman-4,4'-哌啶]并检查了它们的生物学活性。几种化合物抑制了化合物48/80诱导的组胺从分离的大鼠腹膜肥大细胞中释放。讨论了本系列中此活动的结构要求。
• Synthesis and structure-activity relationship of spiro(isochromanpiperidine) analogs for inhibition of histamine release. IV.
  作者：KUNIKO HASHIGAKI、KIWAMU HIRAMATSU、MASATOSHI YAMATO、KENJI TASAKA

  DOI：10.1248/cpb.32.3561

  日期：——

  Various 1'-(o, m, and/or p-substituted benzyl) (5), 1'-(heterocyclic arylmethyl) (6), and 1'-acyl (7) analogs of spiro [isochroman-3, 4'-piperidin]-1-one were prepared and tested for inhibitory activity on the compound 48/80-induced release of histamine from mast cells. The biological results suggested that the activity is mainly affected by the lipophilicity rather than by the electrostatic character of the 1'-substituent. 4-Benzylspiro [cyclohexane-1, 3'-hexahydroisochroman]-1'-one (17) and 9-benzyl-1-oxaspiro [5.5] undecan-2-one (18) were prepared and found to be inactive, implying that the benzene moiety in the isochroman ring is essential for the activity.

  制备了多种 1'-（邻、间和/或对取代的苄基）(5)、1'-（杂环芳甲基）(6) 和 1'-酰基 (7) 的螺[异苯并吡喃-3, 4'-哌啶]-1-酮类似物，并测试了这些类似物对化合物 48/80 诱导的肥大细胞释放组胺的抑制活性。生物学结果表明，其活性主要受亲脂性而非 1'- 取代基的静电特性的影响。制备了 4-苄螺[环己烷-1，3'-六氢异苯并吡喃]-1'-酮（17）和 9-苄基-1-氧杂螺[5.5]十一烷-2-酮（18），发现它们没有活性，这意味着异苯并吡喃环中的苯分子对活性至关重要。
• NOVEL SPIRO COMPOUNDS USEFUL AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE
  申请人：Lachance Nicolas

  公开号：US20110312952A1

  公开（公告）日：2011-12-22

  Heteroaromatic compounds of structural formula (I) are selective inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD1) relative to other known stearoyl-coenzyme A desaturases. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, such as atherosclerosis; obesity; diabetes; neurological disease; metabolic syndrome; insulin resistance; and liver steatosis.

  结构式（I）的杂环芳香化合物是选择性的硬脂酰辅酶A-Δ9-脱饱和酶（SCD1）抑制剂，相对于其他已知的硬脂酰辅酶A脱饱和酶。本发明的化合物对于预防和治疗与异常脂质合成和代谢相关的疾病非常有用，包括心血管疾病，如动脉粥样硬化；肥胖症；糖尿病；神经系统疾病；代谢综合征；胰岛素抵抗和肝脂肪变性。
• Development of Photoredox Cross-Electrophile Coupling of Strained Heterocycles with Aryl Bromides Using High-Throughput Experimentation for Library Construction
  作者：Yukiko Mori、Mutsuyo Hayashi、Ryuma Sato、Kuninori Tai、Tsuyoshi Nagase

  DOI：10.1021/acs.orglett.3c01821

  日期：2023.8.4

  cross-coupling reaction of aryl halides with strained aliphatic heterocycles facilitated via a ring-opening reaction. This methodology was found to be applicable to medicinally relevant substrates including Boc-protected strained aliphatic heterocycles and (hetero)aryl bromides and was used for compound library construction via parallel medicinal chemistry. Furthermore, the coupling reactions were shown

  采用微型高通量实验开发了芳基卤化物与张力脂肪族杂环通过开环反应促进的光氧化还原辅助还原交叉偶联反应。该方法被发现适用于医学相关底物，包括 Boc 保护的应变脂肪族杂环和（杂）芳基溴，并用于通过平行药物化学构建化合物库。此外，通过连续流动反应，偶联反应可扩展到克级。还讨论了可能的反应机理。
• Compound or pharmaceutically acceptable salt thereof
  申请人：RIKEN

  公开号：US11414429B2

  公开（公告）日：2022-08-16

  Provided are 2-(piperidin-1-yl)pyrimidin-4(3H)-ones or pharmaceutically acceptable salts thereof, each characterized by having a 1,8-diazaspiro[4.5]deca-3-ene, 1-oxa-8-azaspiro[4.5]deca-3-ene, 2,8-diazaspiro[4.5]deca-3-ene, 2-oxa-8-azaspiro[4.5]deca-3-ene, 2,9-diazaspiro[5.5]undeca-3-ene, 1-oxa-9-azaspiro[5.5]undeca-3-ene, 1,9-diazaspiro[5.5]undeca-4-ene, or 3,9-diazaspiro[5.5]undeca-1-ene structure represented by the following general formula (1):

  本发明提供了 2-(哌啶-1-基)嘧啶-4(3H)-酮或其药学上可接受的盐，其特征在于每种都具有 1,8-二氮杂螺[4.5]癸-3-烯、1-氧杂-8-氮杂螺[4.5]癸-3-烯、2,8-二氮杂螺[4.5]癸-3-烯、2-氧杂-8-氮杂螺[4.5]癸-3-烯、2,9-二氮杂螺[5.5]十一碳-3-烯、1-氧杂-9-氮杂螺[5.5]十一碳-3-烯、1,9-二氮杂螺[5.5]十一碳-4-烯或 3,9-二氮杂螺[5.5]十一碳-1-烯结构由以下通式 (1) 代表：