Methyl-S-lactate acrylate | 912823-85-9

• 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
• 英文名称: Methyl-S-lactate acrylate
• 英文别名: S-methyl lactate acrylate；methyl (2R)-2-prop-2-enoyloxypropanoate
• CAS: 912823-85-9
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: CPZUGEVUVTWMRE-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-hydroxy-o-quinodimethane 、 Methyl-S-lactate acrylate 以55%的产率得到(S)-Methyl lactate (-)-1-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  Thermal generation of alpha-hydroxy-orthoquinodimethane and reaction with the fumarate, maleate and acrylate of S-methyl lactate

  摘要：

  DOI：

  10.1016/s0040-4039(00)99221-9
• 作为产物：
  描述：

  D-(+)-乳酸甲酯 、 丙烯酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以86%的产率得到Methyl-S-lactate acrylate
  参考文献：
  名称：

  Azomethine Ylides 与衍生自 (S)-和 (R)-乳酸甲酯的手性丙烯酸酯之间的非对映选择性 1,3-偶极环加成反应——丙型肝炎病毒 RNA 依赖性 RNA 聚合酶抑制剂的合成

  摘要：

  描述了衍生自 (R)-和 (S)-乳酸甲酯的丙烯酸酯之间的高度内非对映选择性 1,3-偶极环加成，作为手性偶极亲和物，以及衍生自甘氨酸和 α-取代氨基酸的偶氮甲碱叶立德。观察到的优秀立体控制的起源是在对模型系统的计算研究的基础上解释的。该方法已成功用于首次不对称合成两种对映异构体及其外消旋形式，即包含亮氨酸残基和 2-噻吩基的生物活性吡咯烷（丙型肝炎病毒抑制剂）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  DOI：

  10.1002/ejoc.200700267

文献信息

• 1,3-Dipolar cycloadditions of azomethine ylides with chiral acrylates derived from methyl (S)- and (R)-lactate: diastereo- and enantioselective synthesis of polysubstituted prolines
  作者：Carmen Nájera、M. de Gracia Retamosa、José M. Sansano

  DOI：10.1016/j.tetasy.2006.07.006

  日期：2006.8

  The 1,3-dipolar cycloaddition of acrylates derived from methyl (R)- and (S)-lactate, as chiral dipolarophiles, with glycine and alanine derived azomethine ylides is described for the first time. By using the corresponding silver metallo-azomethine ylides polysubstituted endo-prolines were obtained with high diastereo- and enantioselectivity. The process occurs at room temperature in toluene with 10 mol % of AgOAc by using either KOH or Et3N as bases, also in substoichiometric amounts. Under these mild reaction conditions, enantiomerically enriched polysubstituted prolines resulting from an endo approach were obtained in general in high yields and de (86-99%). The absolute configuration of the resulting prolinates can be determined on the basis of X-ray diffraction analysis. (c) 2006 Elsevier Ltd. All rights reserved.
• Methyl (S)-Lactate as a Chiral Auxiliary in the Asymmetric Synthesis of Bao Gong Teng A
  作者：Vinh C. Pham、James L. Charlton

  DOI：10.1021/jo00129a053

  日期：1995.12

  The asymmetric synthesis of Bao Gong Teng A, (-)-1, a natural product that shows strong antiglaucoma properties, is described. The synthesis begins with an asymmetric 1,3-dipolar cycloaddition of the acrylate of methyl (S)-lactate to the betaine of N-benzyl-3-hydroxypyridinium chloride giving cycloadduct 59 as a major product. The crude cycloadduct was reduced by catalytic hydrogenation to produce 6 in 61% yield. The ketone 6 was reduced with LiAl(OtBu)(3)H to give exo alcohol 7b in 62% yield. Protection of the alcohol group followed by replacement of the benzyl group on the nitrogen with a Boc group gave 12, which was then hydrolyzed to the acid 13 in 91% yield for the three steps. The acid 13 was converted to the ketone 14 in 82% yield via the acid chloride. Baeyer-Villiger oxidation converted 14 to 15 in 52% yield. Optically pure Bao Gong Teng A was obtained in 9% overall yield by the removal of both the Boc and the TBDMS groups using 1% HCl-EtOH.
• Diastereoselective 1,3-Dipolar Cycloaddition Reactions between Azomethine Ylides and Chiral Acrylates Derived from Methyl (S)- and (R)-Lactate – Synthesis of Hepatitis C Virus RNA-Dependent RNA Polymerase Inhibitors
  作者：Carmen Nájera、M. de Gracia Retamosa、José M. Sansano、Abel de Cózar、Fernando P. Cossío

  DOI：10.1002/ejoc.200700267

  日期：2007.10

  Highly endo-diastereoselective 1,3-dipolar cycloadditions between acrylates derived from methyl (R)- and (S)-lactate, as chiral dipolarophiles, and azomethine ylides derived from glycine and α-substituted amino acids are described. The origins of the observed excellent stereocontrol are interpreted on the basis of computational studies on model systems. This methodology was successfully employed for

  描述了衍生自 (R)-和 (S)-乳酸甲酯的丙烯酸酯之间的高度内非对映选择性 1,3-偶极环加成，作为手性偶极亲和物，以及衍生自甘氨酸和 α-取代氨基酸的偶氮甲碱叶立德。观察到的优秀立体控制的起源是在对模型系统的计算研究的基础上解释的。该方法已成功用于首次不对称合成两种对映异构体及其外消旋形式，即包含亮氨酸残基和 2-噻吩基的生物活性吡咯烷（丙型肝炎病毒抑制剂）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Thermal generation of alpha-hydroxy-orthoquinodimethane and reaction with the fumarate, maleate and acrylate of S-methyl lactate
  作者：James L. Charlton、Kevin Koh、Guy L. Plourde

  DOI：10.1016/s0040-4039(00)99221-9

  日期：1989.1