8-chloro-7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one | 53391-77-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-chloro-7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one
• 英文别名: 7-hydroxy-8-chloro-2,3-dihydrocyclopenta[c]chromen-4(1H)-one；8-chloro-7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one；8-Chlor-7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-on；8-chloro-7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one
• CAS: 53391-77-8
• 化学式: C₁₂H₉ClO₃
• mdl: MFCD01472190
• 分子量: 236.655
• InChiKey: HETUGUSWOXYKSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  8-chloro-7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 在 sodium hydroxide 、 potassium carbonate 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 2.0h， 生成 N-[([8-chloro-4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl]oxy)acetyl]cytisine
  参考文献：
  名称：

  Modified coumarins. 22. Synthesis of N-coumarinyloxyacetyl derivatives of cytisine

  摘要：

  合成了由香豆素修饰的N-乙酰胞嘧啶衍生物。

  DOI：

  10.1007/s10600-006-0061-2
• 作为产物：
  描述：

  己二酸二甲酯 在 aluminum (III) chloride 、 bismuth (III) nitrate pentahydrate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 8-chloro-7-hydroxy-2,3-dihydrocyclopenta[c]chromen-4(1H)-one
  参考文献：
  名称：

  Synthesis and evaluation of new coumarin derivatives as potential atypical antipsychotics

  摘要：

  In this paper, we report the synthesis of novel, potential antipsychotic coumarin derivatives combining potent dopamine D-2, D-3 and serotonin 5-HT1A 5-HT(2)A receptors properties. We describe the structure activity relationship that leads us to the promising derivative: 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl) piperidin-1-yl)butoxy)-6-methyl-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 27. The unique pharmacological features of compound 27 are a high affinity for dopamine D-2, D-3 and serotonin 5-HT1A, 5-HT2A receptors, together with a low affinity for H-1 receptor (to reduce the risk of obesity under chronic treatment). In animal models, compound 27 inhibited apomorphine-induced climbing and MK-801-induced hyperactivity without observable catalepsy at the highest dose tested. In particular, compound 27 was more potent than clozapine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.012

文献信息

• Modified Coumarins. 39. Synthesis of Aloperine-Containing Mannich Bases of 7-Hydroxycoumarins
  作者：Ya. L. Garazd、M. M. Garazd

  DOI：10.1007/s10600-017-2019-y

  日期：2017.5

  The possibility of using the alkaloid aloperine for aminomethylation of hydroxycoumarins was investigated. Series of substituted 6- and 8-(aloperin-1-yl)methyl derivatives of 7-hydroxycoumarins were synthesized.

  考察了利用生物碱阿洛培林对羟基香豆素进行氨基甲基化的可能性。合成了一系列的取代的6-和8-(阿洛培林-1-基)甲基7-羟基香豆素衍生物。
• Modified Coumarins. 11. Synthesis and Biological Activity of Mannich Bases of Substituted 1,3-Dihydrocyclopenta[c]chromen-4-ones
  作者：Ya. L. Garazd、T. N. Panteleimonova、M. M. Garazd、V. P. Khilya

  DOI：10.1023/b:conc.0000003410.74701.dc

  日期：2003.7

  Mannich bases containing the dialkylaminomethyl group in the 6- and 8-positions of 2,3-di-hydrocyclopenta[c]chromen-4-ones were prepared by condensation of 7- and 9-hydroxy-2,3-dihydrocyclopenta[c]chromen-4-ones with substituted 1,1-diaminomethanes. The effects of 8-chloro-7-hydroxy-6-(1-pyrrolidinylmethyl)-2,3-dihydrocyclopenta[c]chromen-4-one and 8-chloro-7-hydroxy-6-(morpholinomethyl)-2,3-dihyd

  曼尼希碱在 2,3-di-hydrocyclopenta[c]chromen-4-ones 的 6-和 8-位含有二烷基氨基甲基，是通过 7-和 9-羟基-2,3-dihydrocyclopenta[c] 缩合制备的chromen-4-ones 与取代的 1,1-二氨基甲烷。8-chloro-7-hydroxy-6-(1-pyrrolidinylmethyl)-2,3-dihydrocyclopenta[c]chromen-4-one 和 8-chloro-7-hydroxy-6-(morpholinomethyl)-2,3 的作用-dihydrocyclopenta[c]chromen-4-one 对中枢和外周神经系统进行了定义，并能够预测镇静和精神安定特性的存在。
• Losco; Peri, Gazzetta Chimica Italiana, 1959, vol. 89, p. 1298,1304
  作者：Losco、Peri

  DOI：——

  日期：——
• CHROMENONES AND THEIR USE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
  申请人：Merz Pharma GmbH & Co.KGaA

  公开号：EP1957475A1

  公开（公告）日：2008-08-20
• [EN] CHROMENONES AND THEIR USE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] CHROMENONES ET LEUR UTILISATION EN TANT QUE MODULATEURS DES RECEPTEURS METABOTROPES AU GLUTAMATE
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2007045876A1

  公开（公告）日：2007-04-26

  [EN] The invention relates to chromenone derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are Group I mGluR modulators and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.
  [FR] L'invention concerne des dérivés chroménone ainsi que leurs sels pharmaceutiquement acceptables. L'invention concerne également un procédé de préparation de ces composés. Les composés de l'invention sont des modulateurs des mGluR du Groupe I ; ils sont par conséquent utiles dans le cadre de la régulation et de la prévention des troubles neurologiques aigus et/ou chroniques.