3-苯基-8-甲基-1-氧杂-2,8-二氮杂螺[4,5]癸-2-烯 | 156339-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: 3-苯基-8-甲基-1-氧杂-2,8-二氮杂螺[4,5]癸-2-烯
• 英文名称: 3-phenyl-8-methyl-1-oxa-2,8-diazaspiro<4,5>dec-2-ene
• 英文别名: 8-methyl-3-phenyl-1-oxa-2,8-diazaspiro<4.5>dec-2-ene；8-Methyl-3-phenyl-1-oxa-2,8-diazaspiro[4.5]dec-2-ene
• CAS: 156339-90-1
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: LWCYFOWRXDNDCP-UHFFFAOYSA-N

物化性质

• 沸点：
  337.0±52.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-苯基-8-甲基-1-氧杂-2,8-二氮杂螺[4,5]癸-2-烯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以75%的产率得到1-methyl-4-hydroxy-4-(2'-phenyl-2'-aminoethyl)-piperidine
  参考文献：
  名称：

  Synthesis of spiro-substituted 1,3-oxazines by a new sequence leading to spiroheterocycles

  摘要：

  The target compounds, i.e. 1,3-oxazines which are spiro-substituted in position 6 by a piperidine moiety, are derived from 1-oxa-3,9-diaza-spiro [5.5]undecane, a novel heterocyclic parent system. They were all approached by the following three-step sequence: 1,3-dipolar cycloadditions of nitrile oxides and nitrones to piperidines bearing an exocyclic methylene group gave the corresponding spiro-substituted oxazole derivatives 3. In a consecutive step these were cleaved by hydrogenolysis to gamma-amino-alcohols 4, which in a final step were recyclized by insertions of a C-1-unit to yield the target structures 5-10: thus a de facto ring-extension of spiro-oxazoles to spiro-oxazines was accomplished.

  DOI：

  10.1007/bf00812705
• 作为产物：
  描述：

  1-甲基-4-亚甲基哌啶 、 苯甲腈 N-氧化物 生成 3-苯基-8-甲基-1-氧杂-2,8-二氮杂螺[4,5]癸-2-烯
  参考文献：
  名称：

  Synthesis of spiro-substituted 1,3-oxazines by a new sequence leading to spiroheterocycles

  摘要：

  The target compounds, i.e. 1,3-oxazines which are spiro-substituted in position 6 by a piperidine moiety, are derived from 1-oxa-3,9-diaza-spiro [5.5]undecane, a novel heterocyclic parent system. They were all approached by the following three-step sequence: 1,3-dipolar cycloadditions of nitrile oxides and nitrones to piperidines bearing an exocyclic methylene group gave the corresponding spiro-substituted oxazole derivatives 3. In a consecutive step these were cleaved by hydrogenolysis to gamma-amino-alcohols 4, which in a final step were recyclized by insertions of a C-1-unit to yield the target structures 5-10: thus a de facto ring-extension of spiro-oxazoles to spiro-oxazines was accomplished.

  DOI：

  10.1007/bf00812705

文献信息

• NOVEL VANILLOID RECEPTOR LIGANDS AND USE THEREOF FOR THE PRODUCTION OF PHARMACEUTICAL PREPARATIONS
  申请人：Lee Jeewoo

  公开号：US20070105861A1

  公开（公告）日：2007-05-10

  The present invention relates to novel vanilloid receptor ligands, to a process for the production thereof, to pharmaceutical preparations containing these compounds and to the use of these compounds for the production of pharmaceutical preparations.

  本发明涉及新型辣椒素受体配体，以及用于其生产的方法，含有这些化合物的药物制剂以及利用这些化合物生产药物制剂的用途。
• Cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine: Studies in regio- and stereoselectivity
  作者：L. Fišera、F. Sauter、J. Fröhlich、Y. Feng、P. Ertl、K. Mereiter

  DOI：10.1007/bf00811848

  日期：1994.5

  A series of spiro-substituted isoxazole derivatives were synthesized by 1,3-dipolar cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine. Since nmr studies confirmed that only one regioisomer was formed selectively, semi-empirical quantum mechanical methods (AM1) were used to rationalize this regiochemical preference via calculation and inspection of HOMO-LUMO-energy and coefficients. X-ray structure analysis carried out for one of these products showed the occurrence of only one stereoisomer, explicable by comparing AM1-calculated DELTAH(f)-values of all possible cycloadducts.
• Fiera L., Sauter F., Froehlich J., Feng Y., Mereiter K., Monatsh. Chem, 125 (1994) N 8-9, S 909-919
  作者：Fiera L., Sauter F., Froehlich J., Feng Y., Mereiter K.

  DOI：——

  日期：——
• Novel Vanilloid Receptor Ligands and Use Thereof for the Production of Pharmaceutical Preparations
  申请人：Gruenenthal GmbH

  公开号：US20140179686A1

  公开（公告）日：2014-06-26

  The present invention relates to novel vanilloid receptor ligands, to a process for the production thereof, to pharmaceutical preparations containing these compounds and to the use of these compounds for the production of pharmaceutical preparations.
• US8710233B2
  申请人：——

  公开号：US8710233B2

  公开（公告）日：2014-04-29