Decanophenon-dimethylketal | 1153-15-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Decanophenon-dimethylketal
• 英文别名: 1,1-dimethoxydecylbenzene
• CAS: 1153-15-7
• 化学式: C₁₈H₃₀O₂
• 分子量: 278.435
• InChiKey: VFXBUDUSFLYBOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Decanophenon-dimethylketal 在 磷酸二氢铵 作用下， 生成 α-Methoxy-β-octyl-styrol
  参考文献：
  名称：

  ESTER HYDRAZONES AS POSSIBLE PRECURSORS TO ALKOXYDIAZOALKANES: II. THE DECOMPOSITION OF ESTER (p-TOLYLSULFONYL) HYDRAZONE SALTS IN APROTIC SOLVENTS

  摘要：

  在1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或二甘醇中，对甲苯磺酰基苯甲酸甲酯的热分解和光化学分解会产生苯甲醛二甲基缩醛、苯甲酸甲酯腙（II）、meso-1,2-二苯基-1,2-二甲氧基乙烷和甲基α-(对甲苯磺酰基)苄醚。在存在己烯二酸二乙酯的情况下，热分解产生了产率为62%的二乙酯3-甲氧基-3-苯基-反-1,2-环丙烷二甲酸酯（XIV）；在1-癸烯中形成了产率为4%的1-甲氧基-2-正辛基-1-苯基环丙烷（V）的两种异构体，热分解和光化学分解钾4-戊烯基苯甲酸甲酯（对甲苯磺酰基）腙（XVIII）分别产生了1-苯基-2-氧代双环[4.1.0]庚烷（XXI），产率分别为14%和21%。这些产物为烷氧基重氮烷和烷氧基碳负离子在酯（对甲苯磺酰基）腙盐分解中的发生提供了额外证据，并暗示了烷氧基碳负离子可能是可能的中间体。

  DOI：

  10.1139/v65-047
• 作为产物：
  描述：

  癸酰氯 在 三氯化铝 作用下， 生成 Decanophenon-dimethylketal
  参考文献：
  名称：

  ESTER HYDRAZONES AS POSSIBLE PRECURSORS TO ALKOXYDIAZOALKANES: II. THE DECOMPOSITION OF ESTER (p-TOLYLSULFONYL) HYDRAZONE SALTS IN APROTIC SOLVENTS

  摘要：

  在1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或二甘醇中，对甲苯磺酰基苯甲酸甲酯的热分解和光化学分解会产生苯甲醛二甲基缩醛、苯甲酸甲酯腙（II）、meso-1,2-二苯基-1,2-二甲氧基乙烷和甲基α-(对甲苯磺酰基)苄醚。在存在己烯二酸二乙酯的情况下，热分解产生了产率为62%的二乙酯3-甲氧基-3-苯基-反-1,2-环丙烷二甲酸酯（XIV）；在1-癸烯中形成了产率为4%的1-甲氧基-2-正辛基-1-苯基环丙烷（V）的两种异构体，热分解和光化学分解钾4-戊烯基苯甲酸甲酯（对甲苯磺酰基）腙（XVIII）分别产生了1-苯基-2-氧代双环[4.1.0]庚烷（XXI），产率分别为14%和21%。这些产物为烷氧基重氮烷和烷氧基碳负离子在酯（对甲苯磺酰基）腙盐分解中的发生提供了额外证据，并暗示了烷氧基碳负离子可能是可能的中间体。

  DOI：

  10.1139/v65-047

文献信息

• Analogs of the dioxolanes dexoxadrol and etoxadrol as potential phencyclidine-like agents. Synthesis and structure activity relationships
  作者：Andrew Thurkauf、Mariena V. Mattson、Scott Richardson、Seid Mirsadeghi、Paul L. Ornstein、Ernest A. Harrison、Kenner C. Rice、Arthur E. Jacobson、James A. Monn

  DOI：10.1021/jm00086a001

  日期：1992.4

  A series of dioxolane analogues based on dexoxadrol ((4S,6S)-2,2-diphenyl-4-(2-piperidyl)-1,3-dioxolane) and etoxadrol ((2S,4S,6S)-2-ethyl-2-phenyl-4-(2-piperidyl)-1,3-dioxolane) were prepared and tested for their ability to displace [H-3]TCP (1-[1-(2-thienyl)cyclohexyl]piperidine) from PCP (1-(1-phenylcyclohexyl)piperidine) binding sites in rat brain tissue homogenates. Qualitative structure-activity relationships within this series were explored through modifications of the three major structural units of dexoxadrol, the piperidine, 1,3-dioxolane, and aromatic rings of the molecule. N-Alkyl derivatives of dexoxadrol were found to be inactive, as were those analogues where the dioxolane ring was modified. Phenyl-substituted etoxadrol analogues were compared to similarly substituted PCP analogues and distinct differences were found in their structure-activity relationships suggesting that the aromatic rings in these two drug classes interact differently with the PCP binding sites. The replacement of the phenyl ring in etoxadrol by either a 2- or 3-thienyl ring led to compounds with affinity comparable to etoxadrol, and the replacement of the ethyl moiety on etoxadrol's dioxolane ring with propyl (7) or isopropyl (8) led to compounds which were more potent than etoxadrol or PCP. The most potent compound was (2S,4S,6S)-2-ethyl-2-(1-chlorophenyl)-4-(2-piperidyl)-1,3-dioxolane (11), where a chlorine moiety was placed in the ortho position in the aromatic ring of etoxadrol. Its potency was comparable with TCP in vitro.
• ESTER HYDRAZONES AS POSSIBLE PRECURSORS TO ALKOXYDIAZOALKANES: II. THE DECOMPOSITION OF ESTER (<i>p</i>-TOLYLSULFONYL) HYDRAZONE SALTS IN APROTIC SOLVENTS
  作者：Robert J. Crawford、Rintje Raap

  DOI：10.1139/v65-047

  日期：1965.2.1

  The thermal and photochemical decomposition of methyl benzoate (p-tolylsulfonyl)hydrazone salts in 1,2-dimethoxyethane, 1,2-diethoxyethane, or diglyme gives rise to benzaldehyde dimethyl acetal, methyl benzoate azine (II), meso-1,2-diphenyl-1,2-dimethoxyethane, and methyl α-(p-tolylsulfonyl)benzyl ether. The thermal decomposition in the presence of diethyl fumarate produced diethyl 3-methoxy-3-phenyl-trans-1,2-cyclopropanedicarboxylate (XIV) in 62% yield; a low yield (4%) of the two isomeric forms of 1-methoxy-2-n-octyl-1-phenyl-cyclopropane (V) was formed in 1-decene. The thermal and photochemical decomposition of potassium 4-pentenyl benzoate (p-tolylsulfonyl)hydrazone (XVIII) produced 1-phenyl-2-oxabicyclo[4.1.0]heptane (XXI) in 14 and 21% yield respectively. These products provide additional evidence for the occurrence of alkoxydiazoalkanes and suggest alkoxycarbenes as possible intermediates in the decomposition of ester (p-tolylsulfonyl)hydrazone salts.

  在1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或二甘醇中，对甲苯磺酰基苯甲酸甲酯的热分解和光化学分解会产生苯甲醛二甲基缩醛、苯甲酸甲酯腙（II）、meso-1,2-二苯基-1,2-二甲氧基乙烷和甲基α-(对甲苯磺酰基)苄醚。在存在己烯二酸二乙酯的情况下，热分解产生了产率为62%的二乙酯3-甲氧基-3-苯基-反-1,2-环丙烷二甲酸酯（XIV）；在1-癸烯中形成了产率为4%的1-甲氧基-2-正辛基-1-苯基环丙烷（V）的两种异构体，热分解和光化学分解钾4-戊烯基苯甲酸甲酯（对甲苯磺酰基）腙（XVIII）分别产生了1-苯基-2-氧代双环[4.1.0]庚烷（XXI），产率分别为14%和21%。这些产物为烷氧基重氮烷和烷氧基碳负离子在酯（对甲苯磺酰基）腙盐分解中的发生提供了额外证据，并暗示了烷氧基碳负离子可能是可能的中间体。