[(2R)-2-(4-methoxyphenyl)propyl] acetate | 460323-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2R)-2-(4-methoxyphenyl)propyl] acetate
• CAS: 460323-57-3
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: NFWGDUCSQFVCGA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  [(2R)-2-(4-methoxyphenyl)propyl] acetate 在 吡啶 、 氢氧化钾 、 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Total synthesis of sporochnols, fish deterrents from a marine alga

  摘要：

  Sporochnols, fish deterrents from a marine alga. were synthesized. using intramolecular C H insertion of alkylidenecarbene as a key step to construct the chiral quaternary center. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00857-2
• 作为产物：
  描述：

  2-(4-methoxyphenyl)propane-1,3-diol 在 4-二甲氨基吡啶 sodium hydroxide 、 sodium tetrahydroborate 、 phosphate buffer 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 [(2R)-2-(4-methoxyphenyl)propyl] acetate
  参考文献：
  名称：

  Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity

  摘要：

  DOI：

  10.1016/s0040-4020(01)87892-3

文献信息

• Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes
  作者：Stefano Serra

  DOI：10.1016/j.tetasy.2011.03.012

  日期：2011.3

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.
• Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity
  作者：Giuseppe Guanti、Enrica Narisano、Tadeusz Podgorski、Sergio Thea、Andrew Williams

  DOI：10.1016/s0040-4020(01)87892-3

  日期：1990.1
• Total synthesis of sporochnols, fish deterrents from a marine alga
  作者：Susumu Ohira、Atsuhito Kuboki、Taisuke Hasegawa、Takato Kikuchi、Tatsuhiko Kutsukake、Maki Nomura

  DOI：10.1016/s0040-4039(02)00857-2

  日期：2002.5

  Sporochnols, fish deterrents from a marine alga. were synthesized. using intramolecular C H insertion of alkylidenecarbene as a key step to construct the chiral quaternary center. (C) 2002 Elsevier Science Ltd. All rights reserved.