2-(4-甲氧基-3-苯基甲氧基苯基)乙醛 | 34016-03-0

• 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: 2-(4-甲氧基-3-苯基甲氧基苯基)乙醛
• 英文名称: 3-benzyloxy-4-methoxyphenylacetaldehyde
• 英文别名: [3-(Benzyloxy)-4-methoxyphenyl]acetaldehyde；2-(4-methoxy-3-phenylmethoxyphenyl)acetaldehyde
• CAS: 34016-03-0
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: DNTJSTJUVFQYTN-UHFFFAOYSA-N

物化性质

• 沸点：
  155 °C(Press: 0.01 Torr)
• 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

反应信息

• 作为反应物：
  描述：

  2-(4-甲氧基-3-苯基甲氧基苯基)乙醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 19.0h， 以33%的产率得到2-(4-甲氧基-3-苯基甲氧基苯基)乙醇
  参考文献：
  名称：

  Lamellarins及其同类物的聚合全合成。

  摘要：

  描述了薄片蛋白S和Z的收敛的全合成。该合成的特征是由酯部分促进的易于获得的α，β-二溴吡咯的卤素舞。所得的β，β'-二溴吡咯经过配体控制的Suzuki-Miyaura偶联，可提供一系列二芳基吡咯衍生物。所建立的合成方法也适用于宁纳林B和卢卡醇A和B的合成。

  DOI：

  10.1021/acs.joc.0c00998
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 lead(IV) acetate 、 苯 作用下， 生成 2-(4-甲氧基-3-苯基甲氧基苯基)乙醛
  参考文献：
  名称：

  Schoepf et al., Justus Liebigs Annalen der Chemie, 1940, vol. 544, p. 30,58

  摘要：

  DOI：

文献信息

• Synthesis of tylophorine
  作者：V.K. Mangla、D.S. Bhakuni

  DOI：10.1016/0040-4020(80)80227-4

  日期：1980.1

  A biogenetic type of synthesis of tylorphorine 12 (3.8% yield, established by a radio-dilution method) was achieved by ferricyanide oxidation of 6,7-di(3-hydroxy-4-methoxyphenyl)-6,7-dehydroindolizidine 10.

  甲生物遗传型tylorphorine的合成的12（3.8％产率，由无线电稀释法建立）是由6,7-二（3-羟基-4-甲氧基苯基）铁氰化物氧化实现-6,7- dehydroindolizidine 10。
• 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).
• Mangla, V. K.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 11, p. 931 - 937
  作者：Mangla, V. K.、Bhakuni, D. S.

  DOI：——

  日期：——
• Strategies for the construction of morphinan alkaloid AB-rings: regioselective Friedel-Crafts-type cyclisations of γ-aryl-β-benzoylamido acids with asymmetrically substituted γ-aryl rings
  作者：Stephen G. Davies、Euan C. Goddard、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、James E. Thomson、Jonathan M. Withey

  DOI：10.1016/j.tetasy.2016.02.010

  日期：2016.4

  The regioselectivity of the Friedel-Crafts-type cyclisation of a range of gamma-aryl-B-benzoylamido acids, bearing oxy substituents at the C(3)- and C(4)-positions of the gamma-aryl ring, has been investigated. In all of the cases examined (with 3,4-dimethoxy, 3,4-methylenedioxy and 3-hydroxy-4-methoxy substituents) the Lewis acid promoted cyclisation proceeds with exclusive regioselectivity for attack at the C(6)-position rather than at the C(2)-position, and furnishes the corresponding N- and O-protected 3-amino-6,7-dihydroxy-1-tetralone derivatives. This inherent regioselectivity can be overturned by the regioselective introduction of chlorine as a blocking group for the C(6)-position; subsequent Lewis acid promoted cyclisation then proceeds with exclusive regioselectivity for attack at the C(2)-position to deliver the corresponding N- and O-protected 3-amino-5-chloro-7,8-dihydroxy-1-tetralone derivative. These complementary cyclisation protocols represent useful methods for the preparation of these benzo-fused carbocyclic ring systems, which are the functionalised AB-rings of a range of morphinan alkaloids. (C) 2016 Published by Elsevier Ltd.
• A New Asymmetric Synthesis of <i>trans</i>-Hydroisoquinolones
  作者：Asayuki Kamatani、Larry E. Overman

  DOI：10.1021/ol015696v

  日期：2001.4.1

  A convenient enantioselective synthesis of trans-hydroisoquinolones is described. This synthesis capitalizes on the ready availability of enantioenriched 2-substituted cyclohexenols by exploiting the asymmetry of an allylic carbon-oxygen sigma bond to control carbon-carbon bond formation in pinacol-terminated cyclizations of N-acyliminium cations.