3-formyl-5-methylsalicyl alcohol isopropylidene acetal | 140875-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 3-formyl-5-methylsalicyl alcohol isopropylidene acetal
• 英文别名: 6-formyl-4-methylsalicyl alcohol isopropylidene acetal；2,2,6-trimethyl-4H-benzo[1,3]dioxine-8-carbaldehyde；3-(hydroxymethyl)-5-methylsalicylaldehyde acetonide；2,2-dimethyl-6-methyl-8-formylbenzo-1,3-dioxin；2,2,6-trimethyl-4H-1,3-benzodioxine-8-carbaldehyde
• CAS: 140875-59-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: JIVNKBQETDDVAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  332.2±42.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-formyl-5-methylsalicyl alcohol isopropylidene acetal 在 盐酸 作用下， 反应 12.0h， 以90%的产率得到3-(氯甲基)-2-羟基-5-甲基苯甲醛
  参考文献：
  名称：

  A Convergent Synthesis of Hexahomotriazacalix[3]arene Macrocycles

  摘要：

  A new, convergent synthesis of hexahomotriazacalix[3] arenes la-e is described. The key transformation in this synthesis involves the coupling of the triamines 4a-d with 2,6-bis(chloromethyl)-4-methylphenol 5 and results in the formation of the hexahomotriazacalix[3] arenes 1a-d in 90-95% yield. The triamines 4a-d were constructed by the one-pot reaction of monochloroaldehyde 3 and a primary amine followed by reduction to yield the triamines 4a-d in 50-55% yield. Deallylation of macrocycle Id was accomplished by palladium catalysis to obtain the N-unsubstituted macrocycle le, which has the potential to be a precursor to a variety of N-substituted hexahomotriazacalix[3] arenes.

  DOI：

  10.1021/jo001094y
• 作为产物：
  描述：

  (2,2,6-trimethyl-4H-benzo[1,3]dioxin-8-yl)-methanol 在 copper(II) 2-ethylhexanoate 乙基烯丙基醚 、 quinuclidine * osmium tetraoxide 、 氧气 作用下， 以 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以97%的产率得到3-formyl-5-methylsalicyl alcohol isopropylidene acetal
  参考文献：
  名称：

  在室温和大气压下，Os / Cu催化的烯丙醇和苄醇的空气氧化。

  摘要：

  [反应：见正文]描述了一种在室温下使用1个大气压的空气氧化伯，仲烯丙基和苄醇的新方案。该程序使用低含量的铜盐和四氧化，它们被奎尼丁活化并被烯烃预还原。烯丙基和苄醇的化学选择性非常高，未观察到过氧化，反应在中性条件下进行。

  DOI：

  10.1021/ol025648q

文献信息

• Intramolecular Diels–Alder reaction in 1-oxaspiro[2.5]octa-5,7-dien-4-one and sigmatropic shifts in excited states: novel route to sterpuranes and linear triquinanes: formal total synthesis of (±)-coriolin
  作者：Vishwakarma Singh、S. Q. Alam

  DOI：10.1039/a908223i

  日期：——

  A novel, stereoselective synthesis of sterpuranes and coriolin via modulation of the photochemical reactivity of a tricyclic system having a β,γ-enone chromophore, which was assembled via intramolecular π4s + π2s cycloaddition of 1-oxaspiro[2.5]octa-5,7-dien-4-ones, is presented.

  本文介绍了一种通过调节具有δ²,δ-烯酮发色团的三环体系的光化学反应活性，立体选择性合成甾呋喃和茱萸素的新方法，该体系是通过 1-氧杂螺[2.5]辛-5,7-二烯-4-酮的分子内Ï4s + Ï2s环加成组装而成的。
• Stereoselective Cyclotetramerization of a 3-(Hydroxymethyl)salicylaldehyde
  作者：Gordon M. Butler、Seth N. Brown、Ryan M. Boger、Michelle T. Ferfolia、Ann C. Fitzgibbons、Amy C. Jongeling、Stephen J. Kelleher、Andrew D. Malec、Jeremiah Malerich、Alison N. Weltner

  DOI：10.1021/ol006630n

  日期：2000.12.1

  Both 3-(hydroxymethyl)-5-methylsalicylaldehyde and its acetonide condense in the presence of hydrogen chloride in ether to form macrocyclic S(4)-symmetric tetraacetal 2. The reaction is completely oligo- and stereoselective, forming only the tetramer and only the achiral (R,S,R,S)-stereoisomer. Acid-catalyzed equilibration studies and molecular mechanics calculations indicate that the stereoselectivity

  3-（羟甲基）-5-甲基水杨醛及其丙酮化物在氯化氢存在下于乙醚中缩合形成大环S（4）-对称四缩醛2。该反应是完全低聚和立体选择性的，仅形成四聚体，仅形成四聚体。非手性（R，S，R，S）-立体异构体。酸催化的平衡研究和分子力学计算表明，立体选择性的起源是热力学的。在晶体中，2的鞍形分子形成同轴堆叠，让人联想到品客薯片的堆积。
• Studies on Enzyme-Cleavable Dialkoxymethyl-<i>cyclo</i>Saligenyl-2′,3′-dideoxy-2′,3′-didehydrothymidine Monophosphates
  作者：Nicolas Gisch、Jan Balzarini、Chris Meier

  DOI：10.1021/jm800853p

  日期：2008.11.13

  Recently we reported on conceptually new enzymatically activated cycloSal-pronucleotides. Now, we developed this concept further with new compounds of this type. The basic idea is fast intracellular cleavage of a functionalized group at the cycloSal residue that results in a rapid delivery of the nucleotide and thus an intracellular enrichment of the nucleotide. The introduction of a higher alkylated acylal group, the di-iso-butyryloxymethyl group, to the aromatic ring led to the expected higher stability of these prodrugs against enzymatic cleavage but also entailed surprisingly a decrease in hydrolysis stabilities and solubility problems. For some compounds, a separation of the two diastereomeric forms (R-P, or S-P) was achieved. By X-ray structure analysis, the absolute configuration at the P-atom was assigned. For all separated diastereomers the (S-P) form showed better antiviral activity than the (R-P) form.
• Novel Crown Ether and Salen Metal Chelation Driven Molecular Pincers
  作者：Aki M. M. Abe、Juho Helaja、Ari M. P. Koskinen

  DOI：10.1021/ol061726o

  日期：2006.9.1

  The synthesis of novel metal chelation driven molecular pincers based on crown ether and salen ligand substructures are described. Their functionality was monitored by fluorescence spectroscopy using pyrene groups as fluorescence probes. The pincer was shown to function reversibly with respect to metal chelation with Zn2+ and also to chelate ditopically with 100 mol % of Zn2+ and 100 mol % Li+ or 200 mol % of Li+ ion.
• INTERMEDIATES FOR HYDROXYLATED CONTRAST ENHANCEMENT AGENTS
  申请人：Grimmond Brian James

  公开号：US20110077396A1

  公开（公告）日：2011-03-31

  In one aspect, the present invention provides a protected ligand precursor having structure XX wherein R 8 is independently at each occurrence a protected hydroxy group, a protected C 1 -C 3 hydroxyalkyl group, or a C 1 -C 3 alkyl group, and b is 0-4; R 9 -R 11 are independently at each occurrence hydrogen, a protected C 1 -C 3 hydroxyalkyl group, or a C 1 -C 3 alkyl group, with the proviso that at least one of R 8 -R 11 is a protected hydroxy group or a protected C 1 -C 3 hydroxyalkyl group; and R 12 and R 13 are independently at each occurrence a protecting group is selected from the group consisting of C 1 -C 30 aliphatic radicals, C 3 -C 30 cycloaliphatic radicals, and C 2 -C 30 aromatic radicals.