丁酸,3-羟基-2-亚甲基-,甲基酯,(3S)- | 112572-93-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 中文名称: 丁酸,3-羟基-2-亚甲基-,甲基酯,(3S)-
• 英文名称: methyl (S)-(-)-3-hydroxy-2-methylenebutanoate
• 英文别名: methyl (S)-3-hydroxy-2-methylenebutanoate；(S)-methyl 3-hydroxy-2-methylenebutanoate；methyl (3S)-3-hydroxy-2-methylidenebutanoate
• CAS: 112572-93-7
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: VLCAYQIMSMPEBW-YFKPBYRVSA-N

物化性质

• 沸点：
  190.4±23.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丁酸,3-羟基-2-亚甲基-,甲基酯,(3S)- 在 Ru(OAc)2((R)-BINAP) 、 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl (2S,3S)-3-hydroxy-2-methylbutanoate
  参考文献：
  名称：

  Kinetic resolution of racemic allylic alcohols by BINAP-ruthenium(II) catalyzed hydrogenation

  摘要：

  DOI：

  10.1021/jo00238a048
• 作为产物：
  描述：

  3-羟基-2-亚甲基丁酸甲酯 生成 丁酸,3-羟基-2-亚甲基-,甲基酯,(3S)-
  参考文献：
  名称：

  Kinetic resolution of racemic allylic alcohols by BINAP-ruthenium(II) catalyzed hydrogenation

  摘要：

  DOI：

  10.1021/jo00238a048

文献信息

• Chiral Lewis Acid-Catalyzed Asymmetric Baylis−Hillman Reactions
  作者：Kung-Shuo Yang、Wei-Der Lee、Jia-Fu Pan、Kwunmin Chen

  DOI：10.1021/jo026318m

  日期：2003.2.1

  acid-catalyzed asymmetric Baylis-Hillman reaction is described. Good to high enantioselectivities were obtained using 3 mol % chiral catalyst. Novel camphor-derived dimerized ligands were prepared from the condensation of (+)-ketopinic acid with the corresponding diamines and hydrazine under acidic conditions. When alpha-naphthyl acrylate was used as a Michael acceptor, the reaction is complete within

  描述了有效的手性路易斯酸催化的不对称Baylis-Hillman反应。使用3mol％的手性催化剂获得良好至高的对映选择性。由（+）-酮酸与相应的二胺和肼在酸性条件下的缩合反应制得了新的樟脑衍生的二聚配体。当使用丙烯酸α-萘基酯作为迈克尔受体时，反应在20分钟内以高的立体选择性和合理的化学收率完成。
• Chiral cheating agent and chiral catlyst
  申请人：——

  公开号：US20040176243A1

  公开（公告）日：2004-09-09

  Chiral chelating agents and chiral catalysts, which are formed from the chiral chelating agents and metal, are described. One chiral chelating agent has a general formula (1) as illustrated below: 1 wherein R represents H, methyl, ethyl, a primary, secondary or tertiary straight, branched or cyclic alkyl group having 3-7 carbon atoms, a heterocyclic or aromatic group, an aromatic group substituted at the 2-, 3- or 4-position, an aromatic-like group, or a naphthyl or naphthyl-derived group, and n is an integer between 0 and 4.

  手性螯合剂和手性催化剂是由手性螯合剂和金属形成的。其中一种手性螯合剂具有如下所示的一般式（1）： 1 其中R代表H、甲基、乙基、具有3-7个碳原子的一级、二级或三级直链、支链或环烷基基团、杂环或芳香基团、在2-、3-或4-位取代的芳香基团、类芳香基团，或者萘基或萘基衍生基团，n为0到4之间的整数。
• Synthesis of Optically Active α-Methylene β-Lactams through Lipase-Catalyzed Kinetic Resolution
  作者：Waldemar Adam、Peter Groer、Hans-Ulrich Humpf、Chantu R. Saha-Möller

  DOI：10.1021/jo0003089

  日期：2000.8.1

  is reported. The optically active alpha-methylene beta-lactams 5a-c, and their corresponding amino acids 6a-c have been readily made available through lipase-catalyzed kinetic resolution in high enantiomeric purity (up to 99% ee). The N-substituted beta-lactam derivatives 4a, b and 10 are not accepted by the lipases and were prepared in optically active form by chemical transformation.

  据报道，一种方便的方法用于制备迄今未知的手性α-亚甲基β-内酰胺衍生物5a，b。光学活性的α-亚甲基β-内酰胺5a-c及其相应的氨基酸6a-c已经可以通过脂肪酶催化的动力学拆分以高对映体纯度（至多99％ee）容易地获得。N-取代的β-内酰胺衍生物4a，b和10不被脂肪酶接受，并且通过化学转化以光学活性形式制备。
• Resolution of α-methylene-β-hydroxy esters catalyzed by free and immobilized Pseudomonas sp. lipase
  作者：M.G. Nascimento、Sandra P. Zanotto、Sı́lvia P. Melegari、Luciano Fernandes、Marcus Mandolesi Sá

  DOI：10.1016/j.tetasy.2003.08.015

  日期：2003.10

  Kinetic resolutions of α-methylene-β-hydroxy esters (Baylis–Hillman products) have been performed via enzymatic enantioselective transesterification with Pseudomonas sp. lipase (PSL), free or immobilized in poly(ethylene) oxide (PEO), silica gel and montmorillonite K10, under different reaction conditions. The corresponding (R)-(+)-acetates from alkyl-substituted racemic alcohols were obtained with

  α-亚甲基-β-羟基酯（Baylis–Hillman产品）的动力学拆分已通过假单胞菌属酶的酶促对映选择性酯交换进行。脂肪酶（PSL），在不同的反应条件下游离或固定在聚环氧乙烷（PEO），硅胶和蒙脱土K10中。使用己烷中的PSL / PEO系统和乙酸乙烯酯作为酰化剂，得到ee> 99％且具有优异至中等转化率的烷基取代的外消旋醇，相应的（R）-（+）-乙酸酯。在这些实验条件下，萘基取代的羟基酯是惰性的。
• A Comparative Study on the Diastereofacial Control in the [4+2] Cycloaddition of Sorbates and the Ene Reaction of Tiglates with Singlet Oxygen and PTAD by a Variety of Chiral Auxiliaries
  作者：Waldemar Adam、Sara G. Bosio、Hans-Georg Degen、Oliver Krebs、Dietmar Stalke、Dirk Schumacher

  DOI：10.1002/1099-0690(200212)2002:23<3944::aid-ejoc3944>3.0.co;2-4

  日期：2002.12

  The auxiliary-induced diastereoselectivities of [4+2] cycloaddition and the ene reaction of singlet oxygen and PTAD through a variety of auxiliaries is studied. The different trends in the diastereoselectivities that are observed for the diverse auxiliaries, which include 2,2-dimethyloxazolidines, a menthol derivative, several related cyclohexanes, and the Oppolzer sultam, are compared and backed by

  研究了 [4+2] 环加成的辅助诱导非对映选择性以及单线态氧和 PTAD 通过各种助剂的烯反应。对不同助剂（包括 2,2-二甲基恶唑烷、薄荷醇衍生物、几种相关的环己烷和 Oppolzer sultam）观察到的非对映选择性的不同趋势进行了比较，并得到了机械解释的支持。通过对两种亲电子试剂和四种不同类型助剂的两种反应模式的概述，单个助剂的优势变得明显和可理解。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)