2-methoxy-2-(4-methoxyphenyl)acetaldehyde | 69098-09-5

• 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: 2-methoxy-2-(4-methoxyphenyl)acetaldehyde
• 英文别名: α-methoxy-2-(4-methoxyphenyl)acetaldehyde
• CAS: 69098-09-5
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: XVEVGCHXQGMECP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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-methoxy-2-(4-methoxyphenyl)acetaldehyde 在 ammonium hydroxide 、 sodium hydroxide 、 silver nitrate 作用下， 以 水 、 甲苯 为溶剂， 生成 2-methoxy-2-(4-methoxyphenyl)acetic acid
  参考文献：
  名称：

  Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation

  摘要：

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.023
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-1,2,2-trimethoxyethane 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 生成 2-methoxy-2-(4-methoxyphenyl)acetaldehyde
  参考文献：
  名称：

  Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation

  摘要：

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.023

文献信息

• Brønsted acid-catalysed desilylative heterocyclisation to form substituted furans
  作者：Emily G. Babcock、Md. Shafiqur Rahman、James E. Taylor

  DOI：10.1039/d2ob01828d

  日期：——

  Heterocyclisation of tert-butyldimethylsilyl (TBS) protected γ-hydroxy-α,β-unsaturated ketones catalysed by para-toluenesulfonic acid (p-TSA) to form substituted furans is reported. The reaction proceeds under mild conditions at room temperature in methanol to give a range of furan products (21 examples, up to 98% yield). Mechanistic experiments suggest the reaction proceeds via in situ deprotection

  报道了由对甲苯磺酸 ( p -TSA) 催化的叔丁基二甲基甲硅烷基 (TBS) 保护的 γ-羟基-α,β-不饱和酮杂环化形成取代呋喃。反应在温和的条件下在室温下在甲醇中进行，得到一系列呋喃产物（21 个实例，高达 98% 的收率）。机理实验表明，反应通过原位脱保护进行，然后进行催化脱水杂环化。
• Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation
  作者：Buddh Singh、Pankaj Gupta、Asha Chaubey、Rajinder Parshad、Shiromani Sharma、Subhash C. Taneja

  DOI：10.1016/j.tetasy.2008.10.023

  日期：2008.11

  A facile and efficient synthesis of optically active alpha-methoxyaryl acetic acids (up to 95% ee), alpha-methoxyaryl ethanols (up to 93% ee) and alpha-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, alpha-hydroxyaryl acetaldehyde acetals. (C) 2008 Elsevier Ltd. All rights reserved.