Benzaldehyde dipent-4-enyl acetal | 2031-48-3

• 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: Benzaldehyde dipent-4-enyl acetal
• 英文别名: dipent-4-enyl benzaldehyde acetal；Benzaldehyd-bis--acetal；Benzaldehyd-bis-(pent-4-en-1-yl)-acetal；Bis(pent-4-enoxy)methylbenzene
• CAS: 2031-48-3
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: YTQKRYAOAQWRRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  327.8±42.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  Benzaldehyde dipent-4-enyl acetal 、 D-葡萄烯糖 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以41%的产率得到Penten-4-yl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Ferrier Rearrangement under Nonacidic Conditions Based on Iodonium-Induced Rearrangements of Allylic n-Pentenyl Esters, n-Pentenyl Glycosides, and Phenyl Thioglycosides

  摘要：

  DOI：

  10.1021/jo00117a042
• 作为产物：
  描述：

  4-戊烯-1-醇 在 盐酸 作用下， 生成 Benzaldehyde dipent-4-enyl acetal
  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

• Dipent-4-enyl acetals as acetalization agents
  作者：Robert Madsen、Bert Fraser-Reid

  DOI：10.1039/c39940000749

  日期：——

  Dipent-4-enyl acetals, which are congeniently prepared by treating ketones or aldehydes with pen-4-enyl alcohol under standard conditions, readily acetalize diols in acetonitrtile solvent, and although neutral promoters such as N-halogenosuccinimides and iodonium dicollidine peerchlorate are effective, the rates and yields are greatly enhanced by the addition of catalytic amounts of an acid.

  4-戊烯基缩醛，通过在标准条件下用4-戊烯醇处理酮或醛而天然制备，在乙腈溶剂中容易缩醛化二醇，尽管中性促进剂如N-卤代琥珀酰亚胺和碘鎓二可力丁高氯酸盐有效，但加入少量酸作为催化剂可以显著提高反应速率和产率。
• Acetal Transfer via Halonium-Ion Induced Reactions of Dipent-4-enyl Acetals: Scope and Mechanism
  作者：Robert Madsen、Bert Fraser-Reid

  DOI：10.1021/jo00108a056

  日期：1995.2
• A Solvation-Assisted Model for Estimating Anomeric Reactivity. Predicted versus Observed Trends in Hydrolysis of <i>n</i>-Pentenyl Glycosides¹
  作者：C. Webster Andrews、Robert Rodebaugh、Bert Fraser-Reid

  DOI：10.1021/jo9601223

  日期：1996.1.1

  An attempt has been made to predict qualitative trends in reactivity at the anomeric center, using N-bromosuccinimide-induced hydrolysis of n-pentenyl glycosides (NPGs) as the experimental model. Calculated relative activation energies based on internal energy differences between a reactant and the associated intermediate are not always in agreement with experimental observations. However, solvation energies obtained by the generalized Born surface area model in MacroModel developed by Still et al. give modified activation energies that are in excellent agreement with the experimentally observed trends. It is shown that the solvation model does not disturb the normally observed reactivity trends that can be rationalized on the basis of internal energies alone. The value of the methodology has been demonstrated for several substrates by first-calculating their relative activation energies, then testing them experimentally, and finding excellent agreement with predictions.
• Ferrier Rearrangement under Nonacidic Conditions Based on Iodonium-Induced Rearrangements of Allylic n-Pentenyl Esters, n-Pentenyl Glycosides, and Phenyl Thioglycosides
  作者：J. Cristobal Lopez、Ana M. Gomez、Serafin Valverde、Bert Fraser-Reid

  DOI：10.1021/jo00117a042

  日期：1995.6
• 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。