1,4-dioxa-spiro[4.5]decane-7-carbaldehyde | 65005-14-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-dioxa-spiro[4.5]decane-7-carbaldehyde
• 英文别名: 1,4-Dioxaspiro[4.5]decane-7-carboxaldehyde；1,4-dioxaspiro[4.5]decane-7-carbaldehyde
• CAS: 65005-14-3
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: WRPQKRVYFYXMLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  268.3±35.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-dioxa-spiro[4.5]decane-7-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以3.08 g的产率得到1,4-dioxaspiro[4.5]decan-7-ylmethanol
  参考文献：
  名称：

  具有5β-羟基的C 19-二萜生物碱的AE环系统的构建

  摘要：

  合成了C 19-二萜生物碱的在C-5具有β-羟基且在C-1具有取代基的AE氮杂双环片段。关键反应包括分子内克莱森型缩合，双重曼尼希反应和在1β取代基的空间效应的帮助下羰基的立体选择性亲核加成。

  DOI：

  10.1016/j.tet.2011.04.062
• 作为产物：
  描述：

  3-羟基环己烷羧酸甲酯 在 chromium(VI) oxide 、 硫酸 、 二异丁基氢化铝 、 APTS 作用下， 以 甲苯 为溶剂， 生成 1,4-dioxa-spiro[4.5]decane-7-carbaldehyde
  参考文献：
  名称：

  Synthesis and pharmacological profile of new 1,3-disubstituted cyclohexanes as leukotriene B4 receptor antagonists

  摘要：

  In the course of developing stable leukotriene B-4 antagonists, we synthesized a novel non aromatic series of compounds containing a 1, 3-disubstituted cyclohexane ring in place of the conjugated double bonds of the natural eicosanoid. The Structure-Activity Relationship (SAR) studies leading to the identification of the acid <(1d)under bar> are described. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00424-6

文献信息

• Synthesis and Structure−Activity Relationships of New 1,3-Disubstituted Cyclohexanes as Structurally Rigid Leukotriene B₄ Receptor Antagonists
  作者：Jean-Marc Poudrel、Pierre Hullot、Jean-Pierre Vidal、Jean-Pierre Girard、Jean-Claude Rossi、Agnès Muller、Claude Bonne、Vladimir Bezuglov、Igor Serkov、Pierre Renard、Bruno Pfeiffer

  DOI：10.1021/jm9910573

  日期：1999.12.1

  A series of 1-hydroxy-3-[3-hydroxy-7-phenyl-1-hepten-1-yl] cyclohexane acetic acid derivatives was designed based on postulated active conformation of leukotriene B-4 (LTB4) and evaluated as human cell surface LTB4 receptor (BLTR) antagonists. Binding was determined through [H-3]LTB4 displacement from human neutrophils and receptor antagonistic assays by in vitro measurements of inhibition of leukocyte chemotaxis induced by LTB4. On the basis of these assays, a structure-affinity relationship was investigated. Optimization of the acid chain length and omega-substitution of a phenyl group on the lipophilic tail were shown to be critical for binding activity. These modifications led to the discovery of compounds with submicromolar potency and selective BLTR antagonism. The most potent compound 3b alpha (IC50 = 250 nM) was found to significantly inhibit oedema formation in a topical model of phorbolester-induced inflammation. Substantial improvement of in vitro potency was achieved by modification of the carboxylic acid function leading to the identification of the N,N-dimethylamide series. Compound 5b alpha, free of agonist activity, displayed higher potency in receptor binding with an IC50 of 40 nM. These results support the hypothesis that the spatial relationship between the carboxylic acid and allylic hydroxyl functions is crucial for high binding affinity with BLTR.
• Leukotriene B 4 photoaffinity probes: design, synthesis and evaluation of new arylazide-1,3-disubstituted cyclohexanes
  作者：Denis Durand、Pierre Hullot、Jean-Pierre Vidal、Jean-Pierre Girard、Jean Louis Banères、Joseph Parello、Agnès Muller、Claude Bonne、Jean-Claude Rossi

  DOI：10.1016/s0960-894x(00)00103-7

  日期：2000.4

  The synthesis and the binding affinities of new leukotriene Bq receptor photoaffinity probes, where a 1,3-disubstitued cyclohexane ring replaces the conjugated Delta(6.7) and Delta(8.9) double bonds of the natural eicosanoid, are described. One enantiomeric componnd, 4b alpha, is specifically cross-linked upon photolysis to the recombinant leukotriene Bq receptor from human origin (h-BLTR) solubilized in a micellar medium. This probe appears as a good candidate for identifying the ligand binding site of this receptor. (C) 2000 Elsevier Science Ltd. All rights reserved.
• COWHERD F. G.; DORIA M.-C.; GALEAZZI E.; MUCHOWSKI J. M., CAN. J. CHEM. <CJCH-AG>, 1977, 55, NO 16, 2919-2929
  作者：COWHERD F. G.、 DORIA M.-C.、 GALEAZZI E.、 MUCHOWSKI J. M.

  DOI：——

  日期：——
• PYRIMIDINES AS SODIUM CHANNEL BLOCKERS
  申请人：Purdue Pharma LP

  公开号：EP2753606B1

  公开（公告）日：2017-07-05
• Construction of AE ring system for the C19-diterpenoid alkaloids with a 5β-hydroxyl group
  作者：Zhan-Kun Yang、Qiao-Hong Chen、Feng-Peng Wang

  DOI：10.1016/j.tet.2011.04.062

  日期：2011.6

  An AE azabicyclic fragment, with a β-hydroxyl group at C-5 and a substituent at C-1, of the C19-diterpenoid alkaloids, was synthesized. The key reactions include an intramolecular Claisen-type condensation, double Mannich reaction, and stereoselective nucleophilic addition of carbonyl group with the assistance of steric effect of 1β-substituent.

  合成了C 19-二萜生物碱的在C-5具有β-羟基且在C-1具有取代基的AE氮杂双环片段。关键反应包括分子内克莱森型缩合，双重曼尼希反应和在1β取代基的空间效应的帮助下羰基的立体选择性亲核加成。