Acetic acid acetoxy-(4-tert-butoxycarbonylamino-phenyl)-methyl ester | 428442-03-9

• 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: Acetic acid acetoxy-(4-tert-butoxycarbonylamino-phenyl)-methyl ester
• 英文别名: 4-(tert-Butoxycarbonylamino)benzylidenediacetate；[acetyloxy-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]methyl] acetate
• CAS: 428442-03-9
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: VPAXNUVMKNLGSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid acetoxy-(4-tert-butoxycarbonylamino-phenyl)-methyl ester 在 氯化锆(IV) 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以86%的产率得到(4-甲酰苯基)-氨基甲酸叔丁酯
  参考文献：
  名称：

  A facile and efficient ZrCl 4 catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage

  摘要：

  A novel, mild and efficient method has been developed for the preparation of geminal-diacetates and dipivalates in high yields through a reaction of aldehydes with acetic anhydride or pivalic anhydride using Zirconium (W) chloride as a catalyst under solvent free conditions. Regeneration of aldehydes from the acylals was also achieved using the same catalyst in CH3OH. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.002
• 作为产物：
  描述：

  乙酸酐 、 (4-甲酰苯基)-氨基甲酸叔丁酯 在 iron(III) trifluoride 作用下， 反应 0.25h， 以92%的产率得到Acetic acid acetoxy-(4-tert-butoxycarbonylamino-phenyl)-methyl ester
  参考文献：
  名称：

  使用氟化铁 (III) 作为新型催化剂将醛轻松高效地转化为 1,1-二乙酸酯（酰基缩醛）

  摘要：

  在室温下，在催化量 (0.1 mol-%) 的氟化铁 (III) 存在下，醛以高产率顺利转化为相应的 1,1-二乙酸酯（酰基缩醛）。本系统的显着特点是反应时间更短、醛的化学选择性保护和无溶剂条件。该程序特别适用于大规模合成，因为从活性、选择性、可重复使用性和经济性的角度来看，该催化剂在制备 1,1-二乙酸酯（酰基缩醛）时非常有效。

  DOI：

  10.1071/ch06166

文献信息

• A Remarkable HBF₄-SiO₂-Catalyzed Synthesis of Acylals from Aldehydes under Solvent-Free Conditions
  作者：Vinod Kamble、Babasaheb Bandgar、Neeta Joshi、Vasant Jamode

  DOI：10.1055/s-2006-950282

  日期：2006.10

  HBF 4 -SiO 2 has been found to be an outstanding catalyst for the protection of carbonyl compounds as acylals under entirely solvent-free conditions. Some of the major advantages of this procedure are high yields, ease of operation, high chemoselectivity, high atom efficiency, and compatibility with other protecting groups.

  已发现 HBF 4 -SiO 2 是一种出色的催化剂，用于在完全无溶剂的条件下保护作为酰基的羰基化合物。该方法的一些主要优点是收率高、易于操作、化学选择性高、原子效率高以及与其他保护基团的相容性。
• AN EFFICIENT BIOMIMETIC CLEAVAGE OF<i>GEM</i>-DIACETATES TO ALDEHYDES BY β-CYCLODEXTRIN UNDER NEUTRAL CONDITIONS IN AQUEOUS MEDIUM*
  作者：M. Arjun Reddy、L. Rajender Reddy、N. Bhanumathi、K. Rama Rao

  DOI：10.1081/scc-120002012

  日期：2002.1
• A Facile and Efficient Conversion of Aldehydes into 1,1-Diacetates (Acylals) using Iron(III) Fluoride as a Novel Catalyst
  作者：V. T. Kamble、R. A. Tayade、B. S. Davane、K. R. Kadam

  DOI：10.1071/ch06166

  日期：——

  Aldehydes are smoothly converted into the corresponding 1,1-diacetates (acylals) in high yields in the presence of a catalytic amount (0.1 mol-%) of iron(III) fluoride at room temperature. The noteworthy features of the present system are shorter reaction times, chemoselective protection of aldehydes, and solvent-free conditions. The procedure is especially useful for large-scale syntheses as the catalyst

  在室温下，在催化量 (0.1 mol-%) 的氟化铁 (III) 存在下，醛以高产率顺利转化为相应的 1,1-二乙酸酯（酰基缩醛）。本系统的显着特点是反应时间更短、醛的化学选择性保护和无溶剂条件。该程序特别适用于大规模合成，因为从活性、选择性、可重复使用性和经济性的角度来看，该催化剂在制备 1,1-二乙酸酯（酰基缩醛）时非常有效。
• A facile and efficient ZrCl 4 catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage
  作者：G Smitha、Ch.Sanjeeva Reddy

  DOI：10.1016/j.tet.2003.10.002

  日期：2003.11

  A novel, mild and efficient method has been developed for the preparation of geminal-diacetates and dipivalates in high yields through a reaction of aldehydes with acetic anhydride or pivalic anhydride using Zirconium (W) chloride as a catalyst under solvent free conditions. Regeneration of aldehydes from the acylals was also achieved using the same catalyst in CH3OH. (C) 2003 Elsevier Ltd. All rights reserved.