5-acetoxymethyl-2-methoxyphenyl acetate | 63866-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 5-acetoxymethyl-2-methoxyphenyl acetate
• 英文别名: Isovanillinalkoholdiacetat；Acetic acid 5-acetoxymethyl-2-methoxy-phenyl ester；(3-acetyloxy-4-methoxyphenyl)methyl acetate
• CAS: 63866-99-9
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: SRSODAZXLUDDDY-UHFFFAOYSA-N

物化性质

• 沸点：
  282.3±25.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)
• 保留指数：
  1746

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-acetoxymethyl-2-methoxyphenyl acetate 在 phosphate buffer 、 Pseudomonas cepacia PS lipase 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 3-乙酰氧基-4-甲氧基苄醇
  参考文献：
  名称：

  脂肪酶催化羟烷基酚的化学选择性单乙酰化，并从其二乙酸酯化学选择性去除单个乙酰基

  摘要：

  已证明，吸附在硅藻土上的洋葱假单胞菌PS脂肪酶具有催化各种羟烷基酚的化学选择性单乙酰化或从相应的乙酸盐中化学选择去除单个乙酰基的能力。

  DOI：

  10.1016/s0957-4166(98)00285-7
• 作为产物：
  描述：

  胡椒醛 、 二异丁基氢化铝 生成 5-acetoxymethyl-2-methoxyphenyl acetate
  参考文献：
  名称：

  TAKANO, SEIICHI;AKIYAMA, MASASHI;OGASAWARA, KUNIO, HETEROCYCLES, 1983, 20, N 11, 2237-2238

  摘要：

  DOI：

文献信息

• Selective acylation of the phenolic hydroxyl of (hydroxyalkyl)phenols by using vinyl carboxylates as acyl donors in the presence of rubidium fluoride
  作者：Toshifumi Miyazawa、Masato Yamamoto、Hiroshi Danjo

  DOI：10.1007/s00706-013-1019-2

  日期：2013.9

  AbstractHighly selective acylation of the phenolic hydroxy group can be achieved with (hydroxyalkyl)phenols carrying both alcoholic and phenolic hydroxyls by the use of vinyl carboxylates as acyl donors in the presence of rubidium fluoride. Graphical Abstract

  摘要在氟化carrying存在下，通过使用羧酸乙烯酯作为酰基供体，可以同时携带醇羟基和酚羟基的（羟烷基）酚实现酚羟基的高度选择性酰化。 图形概要
• Twisted Amides as Selective Acylating Agents for Hydroxyl Groups under Neutral Conditions:  Models for Activated Peptides during Enzymatic Acyl Transfer Reaction
  作者：Shinji Yamada、Takayuki Sugaki、Kazuhiro Matsuzaki

  DOI：10.1021/jo9522015

  日期：1996.1.1

  The highly twisted amide 2 served as a selective acylating agent; for dials under neutral conditions. The reaction of primary-secondary dials with 2 led to the corresponding primary alkyl monopivalates. For dials containing alcoholic and phenolic hydroxyl groups, alcoholic hydroxyl groups were selectively acylated under neutral conditions, whereas, the opposite selectivity was observed under basic conditions, similar to the cases using acyl halides or acid anhydrides. Although 1 and 3 were unreactive to alcohols, 5-10 having substituent groups at C-4 were reactive to alcohols to give the corresponding acetates or benzoates.
• Takano, Seiichi; Akiyama, Masashi; Ogasawara, Kunio, Heterocycles, 1983, vol. 20, # 11, p. 2237 - 2238
  作者：Takano, Seiichi、Akiyama, Masashi、Ogasawara, Kunio

  DOI：——

  日期：——
• Enzyme-Catalyzed Chemoselective Transesterification Reactions on Hydroxymethylated Phenolic Compounds
  作者：Virinder S. Parmar、Ashok K. Prasad、Hari N. Pati、Rajesh Kumar、Abul Azim、Sucharita Roy、William Errington

  DOI：10.1006/bioo.1998.1117

  日期：1999.4

  The chemoselective capabilities of porcine pancreatic lipase (PPL) in tetrahydrofuran and Candida rugosa lipase (CRL) in diisopropyl ether have been investigated for selective acetylation and deacetylation of hydroxymethylated phenols and hydroxyaryl alkyl ketones and their peracetylated derivatives. Both PPL and CRL exhibited exclusive selectivity for the acetylation of alcoholic hydroxyl group over the phenolic hydroxyl group(s) of the hydroxymethylated phenols 1-5 and aryl alkyl ketones 6-9, and for the deacetylation of ester group involving the phenolic hydroxyl group over the ester group involving alcoholic hydroxyl of the peracetates 19-24. The preliminary results indicate that this strategy of chemoselective acetylation can also be used in the enantiomeric resolution of racemic ketones 6-9. Single crystal X-ray diffraction studies have confirmed the structures of compounds 4, 15, and 17. (C) 1999 Academic Press.
• The acetyl function as a protecting group for phenols
  作者：James Quick、J. Kenneth Crelling

  DOI：10.1021/jo00395a035

  日期：1978.1