1-Hydroxy-1,2,3,4-tetrahydroacridine | 155007-21-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-Hydroxy-1,2,3,4-tetrahydroacridine
• 英文别名: 1,2,3,4-Tetrahydroacridin-1-ol
• CAS: 155007-21-9
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: MGHMJPKLGSHAKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Hydroxy-1,2,3,4-tetrahydroacridine 在 PPA 、 sodium methylate 、 N-溴代乙酰胺 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 9.0h， 生成 1,2-Epoxy-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Synthesis and Solvolysis of Acridine 1,2- and 3,4-Oxides: Crystal Structure of Acridine 1,2-Oxide

  摘要：

  Acridine 1,2- and 3,4-oxides were synthesized from 3,4- and 1,2-dihydroacridine, respectively, via intermediate bromohydrin acetates. Crystals of acridine 1,2-oxide were sufficiently stable to allow the first determination of X-ray crystallographic structural features of a non-K-region arene oxide. Aqueous alkaline hydrolysis of the acridine 1,2- and 3,4-oxides produced trans-1,2-dihydrorxy-1,2-dihydroacridine and trans-3,4-dihydroxy-3,4-dihydroacridine, respectively. The former dihydrodiol was also obtained by a six-step synthesis from 3,4-dihydroacridine. Acid-catalyzed hydrolysis of acridine 1,2-oxide yielded the corresponding cis- and trans-1,2-dihydrodiols (20%) in addition to 1-hydroxy- (12%) and 2-hydroxyacridine (68%). By contrast, solvolysis of acridine 3,4-oxide under acid conditions gave 4-hydroxyacridine as the exclusive product. pH-rate profiles for hydrolysis of the acridine oxides in 1:9 dioxane-water at 25 degrees C were compared with those for anthracene 1,2-oxide, naphthalene 1,2-oxide, and quinoline 5,6- and 7,8-oxides. Second-order rate constants for the hydronium ion-catalyzed ring opening of anthracene 1,2-, acridine 3,4-, and acridine 1,2-oxide are 585, 7.81, and 0.45 M(-1) s(-2), respectively, and are 3-5 times larger than the rate constants for the corresponding naphthalene 1,2-, quinoline 7,8-, and quinoline 5,6-oxides. Rate constants for uncatalyzed ring opening of anthracene 1,2- and acridine 3,4-oxides (117 x 10(-5) s(-1) and 2.4 X 10(-5) s(-1), respectively) are about two to three times larger than the corresponding rate constants for naphthalene 1,2- and quinoline 7,8-oxides, whereas the rate of nucleophilic ring opening by hydroxide ion to give the trans-dihydrodiols is accelerated by less than a factor of 2 for the acridine oxides as compared with their quinoline analogs. The pH-rate profiles for solvolysis of the acridine oxides, like those of the quinoline oxides, exhibit a pH-independent region at pH values below the pK(a) of the ring nitrogen that is attributed to formation of an unreactive N-protonated species.

  DOI：

  10.1021/jo00084a013
• 作为产物：
  描述：

  1-acetoxy-1,2,3,4-tetrahydroacridine 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以80%的产率得到1-Hydroxy-1,2,3,4-tetrahydroacridine
  参考文献：
  名称：

  Simple, Facile, and One-Pot Conversion of the Baylis−Hillman Adducts into Functionalized 1,2,3,4-Tetrahydroacridines and Cyclopenta[b]quinolines

  摘要：

  A simple, facile, and one-pot synthesis of functionalized 1,2,3,4-tetrahydroacridines and cyclopenta[b]-quinolines from the Baylis-Hillman alcohols, i.e., 2-[hydroxy(2-nitroaryl)methyl]cycloalk-2-enones, is described.

  DOI：

  10.1021/jo0489871

文献信息

• Hexahydro-1H-quino[4,3,2-ef][1,4]benzoxazepines and related compounds, a process and intermediates for their preparation and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0430114A2

  公开（公告）日：1991-06-05

  The present invention relates to hexahydro-1 H-quino[4,3,2-ef][1,4]benzoxazepines and related compounds, a process for their preparation and intermediates thereof. The compounds of the invention are able to relieve memory dysfunction, particularly dysfunctions associated with decreased cholinergic activity such as those found in Alzheimer's disease and can, therefore, be used as medicaments.

  本发明涉及六氢-1 H-喹啉并[4,3,2-ef][1,4]苯并氧氮杂卓及相关化合物、其制备工艺及其中间体。 本发明的化合物能够缓解记忆功能障碍，特别是与胆碱能活性降低有关的功能障碍，如阿尔茨海默病中发现的功能障碍，因此可用作药物。
• PHARMACEUTICAL COMPOSITIONS AND USE THEREOF FOR TREATMENT OF NEUROLOGICAL DISEASES AND ETIOLOGICALLY RELATED SYMPTOMOLOGY
  申请人：SHAPIRO, Howard, K.

  公开号：EP0707446A1

  公开（公告）日：1996-04-24
• EP0707446A4
  申请人：——

  公开号：EP0707446A4

  公开（公告）日：2001-01-10
• SAMPLE COLLECTION DEVICES WITH BLOOD STABILIZING AGENTS
  申请人：Becton, Dickinson and Company

  公开号：EP2809289A1

  公开（公告）日：2014-12-10
• TLR INHIBITOR AND BRUTON'S TYROSINE KINASE INHIBITOR COMBINATIONS
  申请人：Pharmacyclics LLC

  公开号：EP3220912A1

  公开（公告）日：2017-09-27