8-苯基-1,4-二oxa-螺[4.5]癸烷-8-羧酸 | 51509-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 8-苯基-1,4-二oxa-螺[4.5]癸烷-8-羧酸
• 英文名称: 8-Phenyl-1,4-dioxaspiro<4.5>decan-8-carbonsaeure
• 英文别名: 8-phenyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid；8-phenyl-1,4-dioxaspiro[4.5]decane-8-carboxylic acid；4-carboxy-4-phenylcyclohexanone, ethylene ketal；4-carboxy-4-phenylcyclohexanone ethylene ketal
• CAS: 51509-99-0
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: TXNFCXPMKUDIMM-UHFFFAOYSA-N

物化性质

• 沸点：
  438.7±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-苯基-1,4-二oxa-螺[4.5]癸烷-8-羧酸 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 N,N-dimethyl-8-phenyl-1,4-dioxaspiro[4.5]decan-8-amine
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014
• 作为产物：
  描述：

  1,5-二氯-3-戊酮 在 氢氧化钾 、 对甲苯磺酸 、 sodium amide 作用下， 以 二氯甲烷 、 水 、 乙二醇 、 二甲基亚砜 为溶剂， 反应 73.0h， 生成 8-苯基-1,4-二oxa-螺[4.5]癸烷-8-羧酸
  参考文献：
  名称：

  4-苯基取代异奎宁环的合成及反应行为

  摘要：

  描述了导致 2-烷基-4-苯基异奎宁环 14 和 15、3,4-二苯基异奎宁环 22-24 和 6-氧代-4-苯基-3-异奎宁酮 (43) 的各种合成路线。在 7-苯基-1.4-二氧杂螺-[4.5] 癸烷-7-甲酰胺 (36) 的酸水解过程中形成的产物的结构通过光谱方法和降解反应阐明。

  DOI：

  10.1002/ardp.19803130603

文献信息

• SUBSTITUTED 4-AMINOCYCLOHEXANE DERIVATIVES
  申请人：NOLTE Bert

  公开号：US20090247530A1

  公开（公告）日：2009-10-01

  The invention relates to compounds that have an affinity to the μ-opioid receptor and the ORL 1-receptor, methods for their production, medications containing these compounds and the use of these compounds for the treatment of pain and other conditions.

  这项发明涉及具有与μ-阿片受体和ORL 1-受体亲和力的化合物，其生产方法，含有这些化合物的药物以及利用这些化合物治疗疼痛和其他疾病的用途。
• 4-Amino-4-phenylcyclohexanone ketal compositions and process of use
  申请人：The Upjohn Company

  公开号：US04065573A1

  公开（公告）日：1977-12-27

  A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.

  一类新的4-氨基-4-芳基环己酮，它们的缩醛和酸盐已经合成，并发现对于缓解动物的疼痛很有用。它们的镇痛活性似乎是很高的，并且一些还表现出对镇痛引起的心血管、呼吸和行为抑制有用的麻醉拮抗活性。其中几种显示出混合的镇痛和麻醉拮抗活性。该类化合物的首选化合物是4-(间羟基苯基)-4-二甲氨基环己酮乙二醚缩醛，以及4-(间羟基苯基)-4-(正丁基甲基氨基)环己酮乙二醚缩醛，作为游离碱和其盐酸盐形式。描述了合成和中间体的过程。披露了单位剂量形式和治疗方法。
• SUBSTITUTED HETEROARYL DERIVATIVES
  申请人：Zemolka Saskia

  公开号：US20100009986A1

  公开（公告）日：2010-01-14

  The invention relates to substituted heteroaryl derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted heteroaryl derivatives for producing medicaments.

  这项发明涉及替代杂环芳基衍生物，涉及其生产方法，含有该化合物的药物以及利用替代杂环芳基衍生物生产药物的用途。
• Spirocyclic Azaindole Derivatives
  申请人：Zemolka Saskia

  公开号：US20090156593A1

  公开（公告）日：2009-06-18

  The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.

  该发明涉及取代的氮杂吲哚衍生物，其制备方法，含有该化合物的药物以及使用取代的氮杂吲哚衍生物来生产药物。
• Benzamide derivatives and uses related thereto
  申请人：Powers P. Jay

  公开号：US20070299080A1

  公开（公告）日：2007-12-27

  Benzamide derivatives of formula I are described and have therapeutic utility, particularly in the treatment of diabetes, obesity and related conditions and disorders: wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and n are as defined herein.

  公式I的苯甲酰胺衍生物已被描述，并具有治疗效用，特别是在治疗糖尿病、肥胖和相关疾病和紊乱方面：其中R1、R2、R3、R4、R5、R6、R7、R8和n如本文所定义。