[4-(苄氧基)-3-甲氧基苯基]乙醛 | 16209-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [4-(苄氧基)-3-甲氧基苯基]乙醛
• 英文名称: <4-(benzyloxy)-3-methoxyphenyl>acetaldehyde
• 英文别名: 2-(4-(benzyloxy)-3-methoxyphenyl)acetaldehyde；(4-benzyloxy-3-methoxy-phenyl)-acetaldehyde；2-(4-benzyloxy-3-methoxyphenyl)acetaldehyde；2-(4-benzyloxy-3-methoxyphenyl)ethanal；3-Methoxy-4-benzyloxyphenylacetaldehyd；3-Methoxy-benzyloxyphenylacetaldehyd；2-(3-methoxy-4-phenylmethoxyphenyl)acetaldehyde
• CAS: 16209-52-2
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: PNNULHYEVCNQRF-UHFFFAOYSA-N

物化性质

• 沸点：
  397.2±32.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  4-苄氧基-3-甲氧基苯乙酸	4-benzyloxy-3-methoxyphenylacetic acid	29973-91-9	C16H16O4	272.301
  4-丙烯基-2-甲氧基苯苄	4-allyl-1-benzyloxy-2-methoxybenzene	57371-42-3	C17H18O2	254.329
  2-(3-甲氧基-4-苯基甲氧基苯基)乙醇	2-(4-(benzyloxy)-3-methoxyphenyl)ethanol	64881-05-6	C16H18O3	258.317
  4-苄氧基-3-甲氧基苯甲醛	3-methoxy-4-(phenylmethoxy)benzaldehyde	2426-87-1	C15H14O3	242.274
  丁香酚	4-allylguaiacol	97-53-0	C10H12O2	164.204
  4-羟基-3-甲氧基苯乙醇	homovanillyl alcohol	2380-78-1	C9H12O3	168.192

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(E)-4-(3-methoxy-4-phenylmethoxyphenyl)-2-methylbut-2-en-1-ol	1256639-99-2	C19H22O3	298.382
  ——	Ethyl 4-(3-methoxy-4-phenylmethoxyphenyl)-3-oxobutanoate	1176900-41-6	C20H22O5	342.392
  ——	1-(4-benzyloxy-3-methoxyphenyl)-2-hydroxydodecan-3-one	909281-87-4	C26H36O4	412.569
  ——	1-(4-benzyloxy-3-methoxy-phenyl)-2-hydroxy-5-methyl-hexan-3-one	915695-41-9	C21H26O4	342.435
  ——	[(2S,3S)-3-[(3-methoxy-4-phenylmethoxyphenyl)methyl]-2-methyloxiran-2-yl]methanol	1256640-00-2	C19H22O4	314.381
  ——	(2RS,5R)-2-hydroxy-5,9-dimethyl-1-(4-benzyloxy-3-methoxyphenyl)dec-8-en-3-one	909281-88-5	C26H34O4	410.554

反应信息

• 作为反应物：
  描述：

  [4-(苄氧基)-3-甲氧基苯基]乙醛 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 aluminum (III) chloride 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 N,N-Diisopropyltryptamine 、 二氢吡啶 、 10% palladium on activated carbon 、 tert-butyl (2R)-2-amino-3-phenylpropanoate;2,2,2-trifluoroacetic acid 、 四丁基氟化铵 、 氢气 、 lithium perchlorate 、 四丁基碘化铵 、 二正丁基氧化锡 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 5,5-dimethyl-1,3-cyclohexadiene 、 癸烷 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 37.58h， 生成 (4aS,5S,7S,8S,9aR)-2-hydroxy-8-methyloctahydro-5,8-epoxy-7,9a-methanobenzo[7]annulen-3(4H)-one
  参考文献：
  名称：

  A Bismuth(III)-Catalyzed Friedel−Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (−)-Platensimycin

  摘要：

  A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

  DOI：

  10.1021/ol102390t
• 作为产物：
  描述：

  丁香酚 在 sodium periodate 、 四氧化锇 、 四丁基碘化铵 、 potassium carbonate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 20.0h， 生成 [4-(苄氧基)-3-甲氧基苯基]乙醛
  参考文献：
  名称：

  A Bismuth(III)-Catalyzed Friedel−Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (−)-Platensimycin

  摘要：

  A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

  DOI：

  10.1021/ol102390t

文献信息

• An Efficient and Facile Synthesis of Capsaicin-Like Compounds as Agonists of the TRPV1 Receptor
  作者：Van H. Tran、Ravi Kantharaj、Basil D. Roufogalis、Colin C. Duke

  DOI：10.1002/ejoc.200600135

  日期：2006.7

  this synthesis was the formation of α-(dimethylamino)alkanenitriles as intermediates. These nitriles were successfully prepared from both aliphatic and aromatic aldehydes by reaction with dimethylamine and aqueous sodium cyanide. Treatment of the nitriles with lithium diisopropylamide (LDA) followed by reaction with various aldehydes led to the formation of α-hydroxy ketone compounds, examples of which

  描述了一种新的通用合成路线，用于制备辣椒素样分子，该分子含有模拟辣椒素结构中酰胺官能团的 α-羟基酮官能团。该合成中的关键反应是形成作为中间体的 α-（二甲氨基）烷腈。通过与二甲胺和氰化钠水溶液反应，由脂肪醛和芳香醛成功地制备了这些腈。用二异丙基氨基锂 (LDA) 处理腈，然后与各种醛反应导致形成 α-羟基酮化合物，其例子包括 2-羟基-1-(4-羟基-3-甲氧基苯基)dodecan-3-一，(5R)-和(5S)-2-羟基-1-(4-羟基-3-甲氧基苯基)-5,9-二甲基dec-8-en-3-one，代表新型辣椒素样分子。(4-苄氧基-3-甲氧基苯基)乙醛的形成也由4-苄氧基-3-甲氧基苯甲醛与叶立德试剂(甲氧基甲基)三苯基溴化鏻的Wittig反应描述，然后酸水解形成标题化合物。这种醛是合成辣椒素样结构的有用前体。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451
• Asymmetric Total Synthesis of (−)-Plicatic Acid via a Highly Enantioselective and Diastereoselective Nucleophilic Epoxidation of Acyclic Trisubstitued Olefins
  作者：Bing-Feng Sun、Ran Hong、Yan-Biao Kang、Li Deng

  DOI：10.1021/ja9039407

  日期：2009.8.5

  The first total synthesis of (-)-plicatic acid has been achieved by a concise and enantioselective route. In this synthesis, a conceptually new strategy featuring an asymmetric epoxidation-intramolecular epoxy-ring-opening Friedel-Crafts reaction sequence was developed for the stereoselective construction of the 2,7'-cyclolignane skeleton bearing contiguous quaternary-quaternary-tertiary stereocenters

  (-)-plicatic acid 的首次全合成是通过简洁的对映选择性路线实现的。在该合成中，开发了一种具有不对称环氧化-分子内环氧-开环 Friedel-Crafts 反应序列的概念性新策略，用于立体选择性构建带有连续四元-四元-叔立体中心的 2,7'-环木脂烷骨架。这一策略的实施是通过使用 TADOOH 开发用于 Seebach 环氧化的改进方案来实现的，该方案提供了前所未有的、高度对映选择性和非对映选择性环氧化，其中包括一系列 α-羰基-β-取代的丙烯酸酯 3。
• Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues
  作者：Denis S. Ermolat'ev、Jitender B. Bariwal、Hans P. L. Steenackers、Sigrid C. J. De Keersmaecker、Erik V. Van der Eycken

  DOI：10.1002/anie.201004256

  日期：2010.12.3

  Alkaloids of the naamine family were synthesized from diverse propargylamines in just two steps (see scheme: R1=Me, R2=substituted benzyl, R3=Ar). Thus, the addition to a propargylamine of a carbodiimide generated in situ, silver(I)‐catalyzed intramolecular hydroamidation, and subsquent deprotection provide access to the heterocyclic core of numerous natural products and biologically active compounds

  纳胺家族的生物碱仅需两个步骤就可以由多种炔丙基胺合成（参见方案：R 1 = Me，R 2 =取代的苄基，R 3 = Ar）。因此，除了在炔丙基胺中原位生成的碳二亚胺之外，银（I）催化的分子内加氢酰胺化作用以及随后的脱保护作用也使人们可以接近许多天然产物和生物活性化合物的杂环核。Boc =叔丁氧羰基，Cbz =碳苄氧基。
• [EN] C-MET MODULATORS AND METHODS OF USE<br/>[FR] MODULATEURS DE C-MET ET PROCEDE D'UTILISATION
  申请人：EXELIXIS INC

  公开号：WO2005030140A2

  公开（公告）日：2005-04-07

  The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. More specifically, the invention provides quinazolines and quinolines which inhibit, regulate and/or modulate kinase receptor, particularly c-Met, KDR, c-Kit, flt-3 and flt-4, signal transduction pathways related to the changes in cellular activities as mentioned above, compositions which contain these compounds, and methods of using them to treat kinase-dependent diseases and conditions. The present invention also provides methods for making compounds as mentioned above, and compositions which contain these compounds.

  本发明提供了一种调节蛋白激酶酶活性的化合物，用于调节细胞活动，如增殖、分化、程序性细胞死亡、迁移和化学入侵。更具体地，本发明提供了喹唑啉和喹啉，其抑制、调节和/或调节激酶受体，特别是c-Met、KDR、c-Kit、flt-3和flt-4，与上述细胞活动变化相关的信号转导途径，包含这些化合物的组合物，以及使用它们治疗激酶依赖性疾病和状况的方法。本发明还提供了制备上述化合物的方法和包含这些化合物的组合物。
• Biosynthesis of tylophorine and tylophorinine
  作者：Dewan S. Bhakuni、Virendra K. Mangla

  DOI：10.1016/s0040-4020(01)92028-9

  日期：1981.1

  Administration of 3,4-dihydroxyphenyl[2-14C]alanine to young Tylophora asthmatica plants revealed that ring B and carbon atoms C9 and C7 of tylophorine and tylophorinine [phenanthroin dolizidine alkaloids] are derived from dopa. Tracer experiments with 6,7-diphenylhexahydroindolizines (1-7) and (26) demonstrated that compound 1 is efficiently and specifically incorporated into tylophorine (13) and tylophorinine (16). Compounds (3), (4) and (26) were not metabolized by the plants to form (13) and (16) whereas (5) and (6) were utilized to yield (13) and (16). Compound (2) was very poorly converted into (13) and (16) and thus is not on the major biosynthetic pathway of (13) and (16).