(S)-methyl 6,7-dihydroxyheptanoate | 1216785-74-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-methyl 6,7-dihydroxyheptanoate
• 英文别名: methyl (S)-6,7-dihydroxyheptanoate；methyl (6S)-6,7-dihydroxyheptanoate
• CAS: 1216785-74-8
• 化学式: C₈H₁₆O₄
• 分子量: 176.213
• InChiKey: RWZWKDZUQKGJFV-ZETCQYMHSA-N

物化性质

• 沸点：
  288.1±30.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲基脂肪酰氯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 dimethyl sulfide borane 、 臭氧 、 N,N-二异丙基乙胺 、 tricyclohexylphosphine tetrafluoroborate 、 (S)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 0.75h， 生成 (S)-methyl 6,7-dihydroxyheptanoate
  参考文献：
  名称：

  anti-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from Dracontium loretense

  摘要：

  Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.

  DOI：

  10.1021/ol501263y

文献信息

• Scope and Mechanism of the Pt-Catalyzed Enantioselective Diboration of Monosubstituted Alkenes
  作者：John R. Coombs、Fredrik Haeffner、Laura T. Kliman、James P. Morken

  DOI：10.1021/ja4041016

  日期：2013.7.31

  The Pt-catalyzed enantioselective diboration of terminal alkenes can be accomplished in an enantioselective fashion in the presence of chiral phosphonite ligands. Optimal procedures and the substrate scope of this transformation are fully investigated. Reaction progress kinetic analysis and kinetic isotope effects suggest that the stereodefining step in the catalytic cycle is olefin migratory insertion

  Pt 催化的末端烯烃的对映选择性二硼化可以在手性亚膦酸酯配体存在下以对映选择性方式完成。对这种转化的最佳程序和底物范围进行了充分研究。反应进程动力学分析和动力学同位素效应表明催化循环中的立体定义步骤是烯烃迁移插入 Pt-B 键。密度泛函理论分析与其他实验数据相结合，表明插入反应将铂定位在基板的内部碳上。该反应的立体化学模型得到了改进，该模型既符合这些特征又符合 Pt-配体复合物的晶体结构。
• l-Threonine-catalysed asymmetric α-hydroxymethylation of cyclohexanone: application to the synthesis of pharmaceutical compounds and natural products
  作者：Anqi Chen、Jin Xu、Winnie Chiang、Christina L.L. Chai

  DOI：10.1016/j.tet.2009.11.100

  日期：2010.2

  L-Threonine has been found to be an efficient catalyst for the asymmetric alpha-hydroxymethylation of cyclohexanone with formalin. Reducing the amount of water in the reaction by the addition of magnesium sulfate as a dehydrating additive significantly improves the yield. Applications of (S)-2-hydroxymethyl cyclohexanone and the chiral building blocks derived therefrom for the synthesis of pharmaceutical compounds and natural products have been explored. (C) 2009 Elsevier Ltd. All rights reserved.
• METHOD OF TREATING DRY EYE DISORDERS AND UVEITIS
  申请人：Alcon, Inc.

  公开号：EP1744736B1

  公开（公告）日：2009-11-18
• [EN] METHOD OF TREATING ASTHMA, ALLERGIC RHINITIS, AND SKIN DISORDERS<br/>[FR] PROCÉDÉ DE TRAITEMENT DE L'ASTHME, DE LA RHINITE ALLERGIQUE ET DE TROUBLES CUTANÉS
  申请人：ALCON MFG LTD

  公开号：WO2008058098A2

  公开（公告）日：2008-05-15

  [EN] The use of 5,6,7-trihydroxyheptanoic acid and analogs is disclosed for the treatment of asthma, allergic rhinitis, and skin disorders such as allergic dermatitis, contact hypersensitivity, urticaria (hives), rosacea, or psoriasis.
  [FR] La présente invention concerne l'utilisation de l'acide 5,6,7-trihydroxyheptanoïque et de ses analogues pour le traitement de l'asthme, de la rhinite allergique, et de troubles cutanés tels qu'une dermatite allergique, une hypersensibilité de contact, un urticaire, une rosacée, ou le psoriasis.
• <i>anti</i>-Diols from α-Oxyaldehydes: Synthesis and Stereochemical Assignment of Oxylipins from <i>Dracontium loretense</i>
  作者：Gayan A. Abeykoon、Shreyosree Chatterjee、Jason S. Chen

  DOI：10.1021/ol501263y

  日期：2014.6.20

  Differentially protected 1,2-diols were synthesized by enantioselective aldehyde α-oxygenation followed by organomagnesium or -lithium addition. Contrary to a previous report, the resultant diols possess an anti configuration. Good selectivity was achieved regardless of the hybridization state of the nucleophile or the presence or absence of branching. This method was applied to short syntheses of all possible stereoisomers of two oxylipins from Dracontium loretense with incomplete stereochemical assignments. Spectroscopic comparisons between the synthetic and natural oxylipins led to unambiguous assignments.