(+/-)-2,2-dimethyl-1a,7b-dihydro-1-oxacyclopropa[a]naphthalen-3(2H)-one | 149455-76-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (+/-)-2,2-dimethyl-1a,7b-dihydro-1-oxacyclopropa[a]naphthalen-3(2H)-one
• 英文别名: 2,2-dimethyl-3,4-epoxy-1,2,3,4-tetrahydronaphthalen-1-one；2,2-dimethyl-1a,7b-dihydronaphtho[1,2-b]oxiren-3-one
• CAS: 149455-76-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: BFPSZGLTUNHXAE-UHFFFAOYSA-N

物化性质

• 沸点：
  289.3±29.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2,2-dimethyl-1a,7b-dihydro-1-oxacyclopropa[a]naphthalen-3(2H)-one 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以53%的产率得到(3S,4S)-4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydronaphthalen-1-one
  参考文献：
  名称：

  2,2-Dialkylnaphthalen-1-ones as new potassium channel activators

  摘要：

  A new series of 2,2-dialkylnaphthalen-1-one potassium channel activators has been prepared, and their in vitro relaxant activities in isolated rat portal vein and guinea pig tracheal spirals as well as their oral antihypertensive effect in spontaneously hypertensive rats have been evaluated. The group of 1,2-dihydro-4-(1,2-dihydro-2-oxo-1-pyridyl)-2,2-dimethylnaphthalen-1-ones with an electron-withdrawing substituent at the 6-position contain the most active compounds and 1,2-dihydro-4-(1,2-dihydro-2-oxo-1-pyridyl)-2,2-dimethyl-1-oxonaphthalene-6-c arbonitrile, 17f (UR-8225), has been selected for further pharmacological development.

  DOI：

  10.1021/jm00067a011
• 作为产物：
  描述：

  1-oxo-2,2-dimethyl-1,2-dihydronaphthalene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到(+/-)-2,2-dimethyl-1a,7b-dihydro-1-oxacyclopropa[a]naphthalen-3(2H)-one
  参考文献：
  名称：

  一种由四氢萘酮衍生的新型手性二醇，用于路易斯酸的络合

  摘要：

  描述了一种基于面-面π-π相互作用的路易斯酸合理设计的新方法。两种新型二醇（-）（1 R，3 R）-2,2-二甲基-1,2,3,4-四氢萘-1,3-二醇（-）- 1和（-）（1 S）的合成从α-四氢萘酮开始，分六个步骤和五个步骤报道了，3 R）-反式-2,2-二甲基-1,2,3,4-四氢萘-1-3-二醇（-）- 9。（-）（1 R，3 R）-2,2-二甲基-1,2,3,4-四氢萘-1,3-二醇（-）- 1的络合 到苯硼酸的Pb表示硼原子和芳环之间的晶面距离为3.05Å，这对于所建议的相互作用是理想的。

  DOI：

  10.1016/s0040-4020(03)01127-x

文献信息

• Tetralones with pharmacological activity
  申请人：J. Uriach & Cia.

  公开号：US05208246A1

  公开（公告）日：1993-05-04

  The present invention relates to new tetralones having the formula I: ##STR1## wherein: R.sup.1 and R.sup.2 represent hydrogen, halogen, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, pentafluoroethyl, ethynyl, trimethylsilylethynyl, C.sub.1-4 alkylcarbonylamino being the amino optionally substituted by a C.sub.1-4 alkyl group; R.sup.3 is hydrogen or C.sub.1-4 alkyl, and R.sup.4 is C.sub.1-4 alkyl, or R.sup.3 and R.sup.4 together form a C.sub.2-5 polymethylene chain; either R.sup.5 represents hydroxyl, acetoxy or formyloxy and R.sup.6 and R.sup.7 are both hydrogen, or R.sup.5 together with R.sup.6 form a carbonyl group and R.sup.7 is hydrogen, or R.sup.5 and R.sup.7 together form a bond and R.sup.6 is hydrogen; R.sup.8 is, among others, 1,2-dihydro-2-oxo-1-pyridyl, 2,3-dihydro-1-oxo-1H-isoindol-2-yl, 2-oxo-1-pyrrolidinyl, 2-oxo-1-pyperidinyl. The invention also relates to a procedure for their preparation and to pharmaceutical compositions containing them. These compounds are antihypertensive and bronchodilator agents.

  本发明涉及具有以下化学式I的新四氢萘：##STR1##其中：R.sup.1和R.sup.2代表氢、卤素、氰基、C.sub.1-4烷基、C.sub.1-4烷氧基、三氟甲基、五氟乙基、乙炔基、三甲基硅基乙炔基、C.sub.1-4烷基羰基氨基，该氨基可能被C.sub.1-4烷基基团取代；R.sup.3为氢或C.sub.1-4烷基，R.sup.4为C.sub.1-4烷基，或R.sup.3和R.sup.4一起形成C.sub.2-5聚亚甲基链；R.sup.5代表羟基、乙酰氧基或甲酰氧基，R.sup.6和R.sup.7都是氢，或者R.sup.5与R.sup.6一起形成羰基，R.sup.7为氢，或者R.sup.5和R.sup.7一起形成键，R.sup.6为氢；R.sup.8为1,2-二氢-2-氧-1-吡啶基、2,3-二氢-1-氧-1H-异吲哚-2-基、2-氧-1-吡咯烷基、2-氧-1-吡哌啶基等。该发明还涉及它们的制备方法和含有它们的药物组合物。这些化合物是抗高血压和支气管扩张剂。
• US5208246A
  申请人：——

  公开号：US5208246A

  公开（公告）日：1993-05-04
• US5272170A
  申请人：——

  公开号：US5272170A

  公开（公告）日：1993-12-21
• 2,2-Dialkylnaphthalen-1-ones as new potassium channel activators
  作者：Carmen Almansa、Luis A. Gomez、Fernando L. Cavalcanti、Ricardo Rodriguez、Elena Carceller、Javier Bartroli、Julian Garcia-Rafanell、Javier Forn

  DOI：10.1021/jm00067a011

  日期：1993.7

  A new series of 2,2-dialkylnaphthalen-1-one potassium channel activators has been prepared, and their in vitro relaxant activities in isolated rat portal vein and guinea pig tracheal spirals as well as their oral antihypertensive effect in spontaneously hypertensive rats have been evaluated. The group of 1,2-dihydro-4-(1,2-dihydro-2-oxo-1-pyridyl)-2,2-dimethylnaphthalen-1-ones with an electron-withdrawing substituent at the 6-position contain the most active compounds and 1,2-dihydro-4-(1,2-dihydro-2-oxo-1-pyridyl)-2,2-dimethyl-1-oxonaphthalene-6-c arbonitrile, 17f (UR-8225), has been selected for further pharmacological development.
• A new chiral diol derived from tetralone for the complexation of Lewis acids
  作者：Michael P Coogan、Robert Haigh、Adrian Hall、Lisa D Harris、David E Hibbs、Robert L Jenkins、Claire L Jones、Nicholas C.O Tomkinson

  DOI：10.1016/s0040-4020(03)01127-x

  日期：2003.9

  A new approach to the rational design of Lewis acids based on face–face π–π interactions is described. The synthesis of two novel diols (−)(1R,3R)-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1,3-diol (−)-1 and (−)(1S,3R)-trans-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene-1-3-diol (−)-9 is reported in six and five steps respectively starting from α-tetralone. Complexation of (−)(1R,3R)-2,2-dimethyl-1,2

  描述了一种基于面-面π-π相互作用的路易斯酸合理设计的新方法。两种新型二醇（-）（1 R，3 R）-2,2-二甲基-1,2,3,4-四氢萘-1,3-二醇（-）- 1和（-）（1 S）的合成从α-四氢萘酮开始，分六个步骤和五个步骤报道了，3 R）-反式-2,2-二甲基-1,2,3,4-四氢萘-1-3-二醇（-）- 9。（-）（1 R，3 R）-2,2-二甲基-1,2,3,4-四氢萘-1,3-二醇（-）- 1的络合 到苯硼酸的Pb表示硼原子和芳环之间的晶面距离为3.05Å，这对于所建议的相互作用是理想的。