(S)-2-甲氧基丙酸甲酯 | 54656-65-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (S)-2-甲氧基丙酸甲酯
• 英文名称: methyl (S)-2-methoxypropanoate
• 英文别名: (S)-2-Methoxypropionic acid methyl ester；methyl (2S)-2-methoxypropanoate
• CAS: 54656-65-4
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: VABBJJOSOCPYIT-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (S)-2-甲氧基丙酸甲酯 在 Nishimura catalyst <(45.9% Rh/19.9% Pt) oxide> 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、10.0 MPa 条件下， 生成 2-甲氧基丙醇
  参考文献：
  名称：

  Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

  摘要：

  The hydrogenation or carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various alpha-amino and alpha-hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields or tire desired amino alcohols and diols were obtained without racemization. The most suitable alpha-substituents were NH2, NHR, and 011, whereas beta-NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was round for alpha-NR2, alpha-OR, and unfunctionalized esters; acids and amides, were also not reduced under these conditions. A working hypothesis for the mode or action of the catalyst is presented.

  DOI：

  10.1002/1615-4169(20011231)343:8<802::aid-adsc802>3.0.co;2-t
• 作为产物：
  描述：

  溴甲烷 、 L-乳酸甲酯 在 silver(l) oxide 作用下， 以 乙醚 为溶剂， 以70%的产率得到(S)-2-甲氧基丙酸甲酯
  参考文献：
  名称：

  手性四苯基乙烯作为cal族和盘状液晶的新型掺杂剂

  摘要：

  制备了三种新的手性四苯基乙烯系列：香茅醛衍生的醚1a，b，乳酸酯衍生的醚2d，g，h，i和乳酸酯衍生的酯3a - c，e - h。螺旋扭转功率（高毒农药）中对这些衍生物确定13，这是足以与所述向列型主体5CB混溶13或盘状向列型主体hexayne 14。对于二元溶液，13 / 1的HTP值为5.7–10.4 µm -1，12.8-16.5微米-1为13 / 2，8.0-28.7微米-1为13 / 3和2.1-2.9微米-1为hexayne 14 / 3进行测定，表明℃之间的更强的相互作用4 -symmetrical propeller-成形tetraphenylethenes 13与calamitc主机5CB 13比具有盘状ç 6 -symmetrical螺旋桨形主机hexayne 14。版权所有©2009 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.1506

文献信息

• The Efficient Synthesis of Alkoxy-esters from Hydroxy Carboxylic Acids Using Dimsyllithium in Dimethylsulfoxide Followed by Alkylation with an Alkyl Halide
  作者：Harry Heaney、Philip Page、Yohan Chan、Matthew McGrath、Eduardo Moreno

  DOI：10.1055/s-2004-834827

  日期：——

  Hydroxy acids are converted directly into the related alkyl ether-alkyl esters in high yields in a single operation by ­double deprotonation using dimsyllithium in dimethylsulfoxide ­followed by treatment with an alkyl halide.

  在单次操作中，通过使用二甲亚砜中的二甲基锂进行双重去质子化，随后用烷基卤处理，羟基酸可以高效地直接转化为相关的烷基醚-烷基酯。
• Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
  作者：Florence Malmedy、Thomas Wirth

  DOI：10.1002/chem.201603022

  日期：2016.11.2

  The first stereoselective version of an iodine(III)‐mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α‐arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid‐based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.

  描述了在原酸酯存在下碘（III）介导的芳基酮重排的第一个立体选择性形式。反应产物α-芳基化酯是生物活性化合物（如布洛芬）合成中非常有用的中间体。使用基于手性乳酸的碘（III）试剂，产品选择性高达73％  ee。
• Preparation of chiral enantiopure 2-(hydroxyalkyl)pyridine derivatives. Use of the chiral pool
  作者：Fredrik Rahm、Robert Stranne、Ulf Bremberg、Kerstin Nordström、Magnus Cernerud、Emmanuel Macedo、Christina Moberg

  DOI：10.1039/b000269k

  日期：——

  Enantiomerically pure 2-(1-hydroxyalkyl)pyridines were prepared via reaction of 2-lithiopyridine with (R)-2,3-O-isopropylideneglyceraldehyde, methyl (S)-2-methoxypropionate and methyl (S)-2-methoxy-2-phenylacetate, obtained from D-mannitol, L-lactic acid and L-mandelic acid, respectively. 6,6′-Bis(1-hydroxyalkyl)-2,2′-bipyridines were obtained from the same naturally occurring chiral compounds and 2-bromo-6-lithiopyridine with subsequent Ni-catalysed coupling.

  通过 2-硫代吡啶与(R)-2,3-O-异亚丙基甘油醛、(S)-2-甲氧基丙酸甲酯和(S)-2-甲氧基-2-苯基乙酸甲酯的反应，制备了对映体纯度较高的 2-(1-羟基烷基)吡啶，这些对映体分别来自 D-甘露醇、L-乳酸和 L-扁桃酸。6,6′-双（1-羟基烷基）-2,2′-联吡啶是由相同的天然手性化合物和 2-溴-6-硫代吡啶经 Ni 催化偶联得到的。
• Hydrophilic Oligo(lactic acid)s Captured by a Hydrophobic Polyaromatic Cavity in Water
  作者：Shunsuke Kusaba、Masahiro Yamashina、Munetaka Akita、Takashi Kikuchi、Michito Yoshizawa

  DOI：10.1002/anie.201800432

  日期：2018.3.26

  owing to effective hydration. Nevertheless, herein we report that the hydrophobic cavity of a polyaromatic capsule, formed through coordination‐driven self‐assembly, can encapsulate hydrophilic oligo(lactic acid)s in water with relatively high binding constants (up to Ka=3×105 m−1). X‐ray crystallographic and ITC analyses revealed that the unusual host–guest behavior is caused by enthalpic stabilization

  由于有效的水合作用，与生物有关的亲水性分子很少与水中的疏水性化合物和表面相互作用。然而，本文我们报道通过配位驱动的自组装形成的聚芳族胶囊的疏水腔可以以较高的结合常数（高达K a = 3×10 5  m）包封亲水性低聚乳酸。-1）。X射线晶体学和ITC分析表明，不寻常的主客体行为是由CH-π和氢键相互作用引起的焓稳定作用引起的。所述多芳族腔稳定可水解的环状二（乳酸），并且即使在水中也优先从低聚（乳酸）的混合物中捕获四（乳酸）。
• Ether-directed diastereoselectivity in catalysed Overman rearrangement: comparative studies of metal catalysts
  作者：Ieva Jaunzeme、Aigars Jirgensons

  DOI：10.1016/j.tet.2008.03.099

  日期：2008.6

  Ether-directed diastereoselectivity in Overman rearrangement of delta-methoxy and delta-TBDMSO substituted allylic trichloroacetimidates has been explored using PtCl2, PtCl4, AuCl and AuCl3 catalysts in comparison with commonly used Pd(II) catalysts. For both substrates the use of PtCl2 catalyst gave notably improved anti/syn-ratio of 1,2-aminoalcohol derivatives (anti/syn=11:1 for 5-methoxy; 6:1 for delta-TBDMSO) compared to all metal catalysts known to promote Overman rearrangement. Formation of 2-trichloromethyloxazoline was observed as a dominant side reaction in the metal catalysed rearrangement of a-methoxy substituted allylic trichloroacetimidates considerably reducing the yield of the desired product. This side reaction was suppressed when delta-TBDMS-ether was used as a directing group. (C) 2008 Elsevier Ltd. All rights reserved.