(R)-1-(2-methoxyphenyl)ethyl acetate | 875901-64-7

• 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: (R)-1-(2-methoxyphenyl)ethyl acetate
• 英文别名: [(1R)-1-(2-methoxyphenyl)ethyl] acetate
• CAS: 875901-64-7
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: ODNKPJFJNXZIFN-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (R)-1-(2-methoxyphenyl)ethyl acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成 (R)-1-(2-甲氧基苯基)乙醇
  参考文献：
  名称：

  Rapid, room-temperature acylative kinetic resolution of sec-alcohols using atropisomeric 4-aminopyridine/triphenylphosphine catalysis

  摘要：

  Two new atropisomeric 4-aminopyridine-based nucleophilic catalysts containing terphenyl 'blocking groups' have been prepared and evaluated for kinetic resolution (KR) of aryl alkyl sec-alcohols. One of these biaryls is shown to be the most selective atropisomeric catalyst yet prepared for several sec-alcohols but its low reactivity makes it non-optimal for use at room temperature (rt). Optimisation of the conditions for conducting KRs at rt using a previously described catalyst (containing a phenyl blocking group) at the 1 mol% level indicates that PPh3 (1 equiv) is beneficial for enantioselectivity and allows KR of (+/-)-1-(naphthyl)ethanol in less than 30 min with s > 15 (i.e. similar to 40% recovered alcohol with > 95% ee). These conditions constitute a convenient and practical method for rapid KR of sec-alcohols and are anticipated to facilitate a detailed kinetic study of this catalytic manifold by calorimetry. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.124
• 作为产物：
  描述：

  乙酸异丙烯酯 、 甲氧基二甲基苄甲醇 在 dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 9.0h， 以97%的产率得到(R)-1-(2-methoxyphenyl)ethyl acetate
  参考文献：
  名称：

  多种仲醇的动态动力学拆分：二羰基氯（戊苄基环戊二烯基）钌和 CAL-B 的合作

  摘要：

  在二羰基氯（戊苄基环戊二烯基）钌和南极念珠菌脂肪酶 B（Novozym435，CAL-B）存在下，在甲苯中使用 31 种结构不同的醇和乙酸异丙烯酯，研究了仲醇动态动力学拆分中的底物范围。酶和钌络合物显示出以高度相容的方式起作用，允许外消旋醇以实际理论产率转化为 (R)-乙酸酯，并且在大多数情况下，ee 值超过 99%。通过使用早期报道的最先进的钌基催化剂进行醇外消旋化，结果与之前发表的结果完全可比。二羰基氯（五苄基环戊二烯基）钌系统的明显优势，

  DOI：

  10.1002/ejoc.201001703

文献信息

• Single-Step Preparation of a 4-(Dimethylamino)pyridine Analogue Bearing a Sulfoxide as New Chiral Inducer. Preliminary Evaluation as Nucleophilic Catalyst
  作者：Vincent Levacher、Thomas Poisson、Maël Penhoat、Cyril Papamicaël、Georges Dupas、Vincent Dalla、Francis Marsais

  DOI：10.1055/s-2005-872256

  日期：——

  A one-step synthesis of a new chiral DMAP-1a equivalent is reported by bromine-magnesium exchange reaction of the 3-bromo-4-(dimethylamino)pyridine (2). The chiral sulfoxide appendage is introduced by trapping the resulting Grignard intermediate with (1R,2S,5R)-(-)-(S)-menthyl p-toluenesulfinate affording (S)-1a in 60% yield and high optical purity. A preliminary evaluation of 1a as nucleophilic catalyst has demonstrated promising selectivity (s = 4.5) during acylative kinetic resolution of various alcohols.

  报道了一种通过3-溴-4-(二甲基氨基)吡啶(2)的溴-镁交换反应，一步合成了新的手性DMAP-1a类似物。通过与(1R,2S,5R)-(-)-(S)-薄荷基对甲苯亚砜酸盐捕获生成的格氏中间体，引入了手性亚砜片段，以60%的产率和高度光学纯度得到了(S)-1a。初步评价1a作为亲核催化剂的效果表明，在各种醇的酰化动力学拆分过程中表现出有希望的选择性(s = 4.5)。
• Asymmetric Chemoenzymatic Reductive Acylation of Ketones by a Combined Iron-Catalyzed Hydrogenation-Racemization and Enzymatic Resolution Cascade
  作者：Osama El-Sepelgy、Aleksandra Brzozowska、Magnus Rueping

  DOI：10.1002/cssc.201700169

  日期：2017.4.22

  A general and practical process for the conversion of prochiral ketones into the corresponding chiral acetates has been realized. An iron carbonyl complex is reported to catalyze the hydrogenation–dehydrogenation–hydrogenation of prochiral ketones. By merging the iron‐catalyzed redox reactions with enantioselective enzymatic acylations a wide range of benzylic, aliphatic and (hetero)aromatic ketones

  已经实现了将前手性酮转化为相应的手性乙酸酯的通用且实用的方法。据报道，羰基铁络合物催化前手性酮的加氢-脱氢-氢化。通过将铁催化的氧化还原反应与对映选择性酶促酰化反应合并，可将各种苄基，脂肪族和（杂）芳族酮以及二酮还原性酰化。分离出高产率和对映选择性的相应产物。铁催化剂与分子氢一起用作氢供体，以及容易获得的乙酸乙酯作为酰基供体一起使用，使得这种级联方法在经济价值和环境信誉方面都非常令人感兴趣。
• CO2-expanded liquids as solvents to enhance activity of Pseudozyma antarctica lipase B towards ortho-substituted 1-phenylethanols
  作者：Moeko Otsu、Yuichi Suzuki、Afifa Ayu Koesoema、Hai Nam Hoang、Mayumi Tamura、Tomoko Matsuda

  DOI：10.1016/j.tetlet.2020.152424

  日期：2020.10

  Pseudozyma (Candida) antarctica lipase B (CAL-B, Novozym 435 (R)) is one of the most widely used and outstanding biocatalysts. However, CAL-B-catalyzed transesterification of ortho-substituted 1-phenylethanol analogs suffers low conversion. In this research, the reactions were accelerated by using CO2-expanded liquids, liquids expanded by dissolving pressurized CO2, such as CO2-expanded hexane or CO2-expanded MeTHF. (C) 2020 Elsevier Ltd. All rights reserved.