Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate | 147849-60-3

• 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: Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate
• 英文别名: (S)-Methyl 4-benzyloxy-3-hydroxybutanoate；methyl (S)-4-benzyloxy-3-hydroxybutanoate；methyl (S)-4-benzyloxy-3-hydroxybutyrate；methyl 3-hydroxy-4-benzyloxybutanoate；Methyl 3S-4-benzyloxy-3-hydroxybutyrate；methyl (3S)-3-hydroxy-4-phenylmethoxybutanoate
• CAS: 147849-60-3
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: CCZLIOHIMSFAIF-NSHDSACASA-N

物化性质

• 沸点：
  350.0±32.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate 在 氢氧化钾 作用下， 反应 18.0h， 以97%的产率得到(S)-4-(Benzyloxy)-3-hydroxybutanoic acid
  参考文献：
  名称：

  Hoffmann, Torsten; Seebach, Dieter, Liebigs Annalen, 1996, # 8, p. 1277 - 1282

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-苄氧甲基环氧乙烷 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 0.92h， 生成 Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate
  参考文献：
  名称：

  三（甲硫基）甲烷与环氧化物的改进反应：在高效合成 β-羟基酯中的应用

  摘要：

  摘要 三（甲硫基）甲基锂在低温下与环氧化物在 THF:HMPA (5:1) 中有效反应，生成 β-羟基邻三硫代羧酸盐，并以高产率转化为 β-羟基酯。

  DOI：

  10.1080/00397919308009842

文献信息

• Macrocyclic compounds as metalloprotease inhibitors
  申请人：DuPont Pharmaceuticals Company

  公开号：US06281352B1

  公开（公告）日：2001-08-28

  This invention relates to macrocyclic molecules which inhibit metalloproteinases, including aggrecanase, and the production of tumor necrosis factor (TNF). In particular, the compounds are inhibitors of metalloproteinases involved in tissue degradation and inhibitors of the release of tumor necrosis factor. The present invention also relates to pharmaceutical compositions comprising such compounds and to methods of using these compounds for the treatment of inflammatory diseases.

  这项发明涉及抑制金属蛋白酶（包括聚集素酶）和肿瘤坏死因子（TNF）产生的大环分子。具体来说，这些化合物是涉及组织降解的金属蛋白酶的抑制剂，也是肿瘤坏死因子释放的抑制剂。本发明还涉及包括这些化合物的药物组合物，以及使用这些化合物治疗炎症性疾病的方法。
• A New Class of Tunable Dendritic Diphosphine Ligands: Synthesis and Applications in the Ru-Catalyzed Asymmetric Hydrogenation of Functionalized Ketones
  作者：Baode Ma、Tingting Miao、Yihua Sun、Yanmei He、Ji Liu、Yu Feng、Hui Chen、Qing-Hua Fan

  DOI：10.1002/chem.201402709

  日期：2014.8.4

  dendritic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β‐ketoesters, α‐ketoesters, and α‐ketoamides to reveal the effects of dendron size on the catalytic properties. The second‐ and third‐generation catalysts exhibited excellent

  一系列可调的G 0 –G 3树枝状2,2'-双（二苯基膦基）-1,1'-联萘（BINAP）配体是通过将聚芳基醚树枝状分子连接到P原子上的四个苯环上而制备的。他们的钌配合物用于β-酮酸酯，α-酮酸酯和α-酮酰胺的不对称氢化反应，揭示了树枝状分子大小对催化性能的影响。第二代和第三代催化剂表现出优异的对映选择性，明显高于从小分子催化剂和第一代催化剂获得的对映选择性。分子模型表明，大的树枝状楔形物的结合会影响金属中心周围的空间环境。此外，
• Enantio- and diastereoselective hetero-Diels–Alder reactions between 2-aza-3-silyloxy-1,3-butadienes and aldehydes catalyzed by chiral dirhodium(ii) carboxamidates
  作者：Yudai Watanabe、Takuya Washio、Janagiraman Krishnamurthi、Masahiro Anada、Shunichi Hashimoto

  DOI：10.1039/c2cc32876c

  日期：——

  The first catalytic asymmetric hetero-Diels–Alder reaction between 2-aza-3-silyloxy-1,3-butadienes and aldehydes is described. With dirhodium(II) tetrakis[N-benzene-fused-phthaloyl-(S)-piperidinonate], Rh2(S-BPTPI)4, the cycloaddition reaction proceeded exclusively in an endo mode to give all-cis-substituted 1,3-oxazinan-4-ones in high yields with up to 98% ee.

  描述了一种首次催化不对称异核Diels–Alder反应，该反应涉及2-氮-3-硅氧基-1,3-丁二烯和醛。在二铑(II)四羧酸盐[N-苯基-融合邻苯二甲酰胺-(S)-哌啶酮]催化下，Rh2(S-BPTPI)4，环加成反应仅以内消旋的方式进行，获得了全顺-取代的1,3-氧杂哌嗪-4-酮，产率高达98%光学纯度。
• An Improved Asymmetric Reformatsky Reaction Mediated by (−)-<i>N</i>,<i>N</i>-Dimethylaminoisoborneol
  作者：Ralf J. Kloetzing、Tobias Thaler、Paul Knochel

  DOI：10.1021/ol0531381

  日期：2006.3.1

  (-)-N,N-Dimethylaminoisoborneol ((-)-DAIB) was found to be an excellent ligand for the enantioselective addition of Reformatsky reagents to aromatic and aliphatic aldehydes. Enantioselectivities up to 93% ee were obtained with sulfur-containing aldehydes.

  (-)-N,N-二甲基氨基异薄荷醇 ((-)-DAIB) 被发现是一种非常适合用于芳香族和脂肪族醛与Reformatsky 试剂进行手性选择性加成的配体。使用含硫的醛类时，获得了高达93% ee的手性选择性效果。
• Organocatalytic Preparation of Simple β-Hydroxy and β-Amino Esters: Low Catalyst Loadings and Gram-Scale Synthesis
  作者：Hao Jiang、Björn Gschwend、Łukasz Albrecht、Karl Anker Jørgensen

  DOI：10.1021/ol102164y

  日期：2010.11.5

  A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence for the synthesis of simple enantioenriched beta-hydroxy and beta-amino esters using commercially available catalysts at low catalyst loadings has been developed. The desired products were obtained in high yield and excellent enantiopurity. The generation of quaternary stereocenters and application in gram-scale synthesis were also realized, with no requirements of inert or anhydrous reaction conditions, thus making this transformation a highly practical protocol.