4-methoxy-3,5-diisopropyloxybenzaldehyde | 171738-31-1

• 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: 4-methoxy-3,5-diisopropyloxybenzaldehyde
• 英文别名: 4-Methoxy-3,5-di(propan-2-yloxy)benzaldehyde
• CAS: 171738-31-1
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: STKPETOZGFSQOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-3,5-diisopropyloxybenzaldehyde 在 palladium on activated charcoal 氢氧化钾 、 lithium hydroxide 、 sodium tetrahydroborate 、 2,4,6-三异丙基苯磺酰叠氮化物 、 氢气 、 双氧水 、 sodium acetate 、 三甲基乙酰氯 、 三溴化磷 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙二醇 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of a model bicyclic C-O-D-O-E ring of vancomycin by a one-pot, double SNAr based macrocyclization

  摘要：

  在–5 °C下，使用CsF处理线性五肽3于DMF中，以一步法的方式得到万古霉素的模型双环CODOE环2。

  DOI：

  10.1039/cc9960001029
• 作为产物：
  描述：

  3,5-二羟基-4-甲氧基苯甲酸甲酯 在 二异丁基氢化铝 、 potassium carbonate 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.25h， 生成 4-methoxy-3,5-diisopropyloxybenzaldehyde
  参考文献：
  名称：

  Sulfinimine-Mediated Asymmetric Synthesis of (R)-(4-Methoxy-3,5-dihydroxyphenyl)glycine:  The Central Amino Acid of Vancomycin and Related Agents

  摘要：

  The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, "EtAl(OR)CN", to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.

  DOI：

  10.1021/jo972076s

文献信息

• Synthesis of β-Amino-α-hydroxy Esters and β-Amino-α-azido Ester by Sharpless Asymmetric Aminohydroxylation, Byproducts Analysis
  作者：Zuosheng Liu、Nianchun Ma、Yanxing Jia、Michèle Bois-Choussy、Adriano Malabarba、Jieping Zhu

  DOI：10.1021/jo047772o

  日期：2005.4.1

  Synthesis of enantiomerically pure β-amino-α-hydroxy esters (1, 2) and β-amino-α-azido ester (3) using Sharpless AA as a key step is described. A hitherto unreported side reaction, the oxidation of the β-hydroxy-α-amino ester (5) into the α,α-di-tert-butyloxycarbamoyl-β-ketoester (8) under AA conditions, is documented.

  对映体纯的合成β氨基α羟基酯（1，2）和β氨基α叠氮基酯（3使用夏普勒斯AA作为关键步骤）进行说明。一个迄今未报告的副反应时，β羟基α氨基酯（氧化5）插入α，α-二-叔butyloxycarbamoyl-β酮酯（8 AA条件下），进行了说明。
• Asymmetric synthesis of 3,5-bis(isopropyloxy)-4-methoxyphenyl glycine by way of a diastereoselective Strecker reaction and an Evans electrophilic amination reaction
  作者：Caroline Vergne、Jean-Philippe Bouillon、Jacqueline Chastanet、Michèle Bois-Choussy、Jieping Zhu

  DOI：10.1016/s0957-4166(98)00312-7

  日期：1998.9

  Two short syntheses of D-N-Boc-3,5-bis(isopropyloxy)-4-methoxyphenyl glycine, a central unit of vancomycin type antibiotics, have been developed. A diastereoselective Strecker reaction using (S)-phenylglycinol as a chiral inducer was the key step in the first synthesis, while Evans' electrophilic amination technology was employed for introducing both the amino function and the chirality in the second strategy. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Chemoenzymatic Synthesis of <scp>d</scp>-<i>N</i>-Boc-3,5- dihydroxy-4-methoxyphenylglycine
  作者：Michèle Bois-Choussy、Jieping Zhu

  DOI：10.1021/jo980233x

  日期：1998.8.1
• Asymmetric synthesis of (2S,3R) β-(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin
  作者：Jieping Zhu、Jean-Philippe Bouillon、Girij Pal Singh、Jacqueline Chastanet、René Bengelmans

  DOI：10.1016/0040-4039(95)01409-b

  日期：1995.9

  The asymmetric synthesis of two appropriately functionalized non-proteinogenic amino acids 2 and 3 needed for the total synthesis of vancomycin was described. The assemblage of these amino acids into linear tripeptide followed by biaryl ether formation via intramolecular SNAr reaction led to the fully functionalized C-O-D ring of vancomycin.
• Sulfinimine-Mediated Asymmetric Synthesis of (<i>R</i>)-(4-Methoxy-3,5-dihydroxyphenyl)glycine:  The Central Amino Acid of Vancomycin and Related Agents
  作者：Franklin A. Davis、Dean L. Fanelli

  DOI：10.1021/jo972076s

  日期：1998.3.1

  The sulfinimine asymmetric Strecker synthesis, the addition of ethyl aluminum cyano alkoxide, "EtAl(OR)CN", to sulfinimine 10, has been applied to a concise highly efficient four-step enantioselective synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine (3) and its derivatives in >97% ee. These epimerization-sensitive arylglycines are precursors of the key central amino acid of vancomycin and related glycopeptide antibiotics.