(S)-1,2-tridecanediol

• 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)-1,2-tridecanediol
• 英文别名: (2S)-tridecane-1,2-diol
• 化学式: C₁₃H₂₈O₂
• 分子量: 216.364
• InChiKey: IOYXJNDDBALLFR-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1,2-tridecanediol 在 palladium on activated charcoal 吡啶 、 正丁基锂 、 三氟化硼乙醚 、 氢气 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 49.5h， 生成 戊基糖三乙酸酯
  参考文献：
  名称：

  不对称合成的5-十六烷醇，东方大黄蜂，Vespa Orientalis女王的信息素

  摘要：

  描述了一种从手性环氧化物有效地不对称合成5-十六烷化物的方法。手性环氧化物的两种对映体形式均可容易地从甘露醇和抗坏血酸获得。合成的关键步骤是使用m-CPBA和BF 3 ·OEt 2从δ-羟基乙缩醛形成δ-内酯。

  DOI：

  10.1016/0040-4020(96)00095-6
• 作为产物：
  描述：

  1-溴十一烷 在 盐酸 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 Aspergillus amino acylase 、 硫酸 、 sodium ethanolate 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 83.0h， 生成 (S)-1,2-tridecanediol
  参考文献：
  名称：

  以（±）-2-氨基十三烷酸的酶促拆分为主要原料，合成大黄蜂女王信息素5-十六烷内酯对映体。

  摘要：

  （±）-2-氯乙酰氨基十三烷酸与氨基酰基酶的光学拆分得到（S）-2-氨基十三烷酸添加物，其被转化为高度光学纯的（S）-5-十六烷化物（Vespa Orientalls的信息素）。类似地，酶水解后回收的（R）-2-氯乙酰基氨基十三烷酸产生（R）-5-十六烷醇化物。严格调查了现有的5-己醇内酯对映体的制备方法，指出了有效手性合成的基本要求。

  DOI：

  10.1016/s0040-4020(01)96498-1

文献信息

• ALDIMINES ET LEURS UTILISATIONS
  申请人：BOSTIK SA

  公开号：EP3838891A1

  公开（公告）日：2021-06-23

  La présente invention concerne des composé ayant l'une des formules (I) ou (II) suivantes : ainsi que leurs utilisations.

  本发明涉及具有下式（I）或（II）之一的化合物： 的化合物及其用途。
• Nandanan; Phukan, Prodeep; Sudalai, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 8, p. 893 - 896
  作者：Nandanan、Phukan, Prodeep、Sudalai

  DOI：——

  日期：——
• Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation
  作者：Gabriella Egri、Eszter Baitz-Gács、László Poppe

  DOI：10.1016/0957-4166(96)00161-9

  日期：1996.5

  Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzyme and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions. Copyright (C) 1996 Elsevier Science Ltd
• Formal synthesis of tetrahydrolipstatin and tetrahydroesterastin
  作者：Divya Tripathi、Pradeep Kumar

  DOI：10.1016/j.tetasy.2012.05.025

  日期：2012.6

  A versatile and efficient approach to (3.5,5R)-methyl 3-(benzyloxy)-5-(methoxymethoxy)hexadecanoate, a key chiral building block and a common polyol fragment of the anti-tumor and anti-obesity agents tetrahydrolipstatin 3 and tetrahydroesterastin 4 using both hydrolytic kinetic resolution (HKR) and proline catalyzed sequential alpha-aminoxylation, followed by HWE-olefination reaction is described. (c) 2012 Elsevier Ltd. All rights reserved.
• ——
  作者：Regine Gries、Grigori Khaskin、Gerhard Gries、Robb G. Bennett、G. G. Skip King、Petra Morewood、Keith N. Slessor、W. Dean Morewood

  DOI：10.1023/a:1021005517389

  日期：——

  Our objectives were to identify and field test the sex pheromone of female Douglas-fir cone gall midge, Contarinia oregonensis (Diptera: Cecidomyiidae). Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses of pheromone extract revealed a single compound (A) that elicited responses from male antennae. Hydrogenation of pheromone extract, followed by renewed GC-EAD analysis, revealed a new EAD-active compound with chromatographic characteristics identical to those of tridecan-2-yl acetate on five fused silica columns (DB-5, DB-210, DB-23, SP-1000, and Cyclodex-B). Syntheses, chromatography, and retention index calculations of all possible tridecen-2-yl acetates suggested that the candidate pheromone A was a tridecadien-2-yl acetate with nonconjugated double bonds. Synthetic candidate pheromone component (Z,Z)-4,7-tridecadien-2-yl acetate (Z4Z7) cochromatographed with A on all analytical columns and elicited comparable antennal activity. In GC-EAD analyses that separated the enantiomers (Z,Z)4,7-tridecadien-(S)-2-yl acetate (2S-Z4Z7) and (Z,Z)-4,7-tridecadien-(R)-2-yl acetate (2R-Z4Z7) with baseline resolution, only 2S-Z4Z7 as a component in a racemic standard or in pheromone extract elicited antennal responses. In Douglas-fir seed orchards, sticky traps baited with 2S-Z4Z7 captured male C. oregonensis, whereas 2R-Z4Z7 was behaviorally benign. Comparable catches of males in traps baited with racemic Z4Z7 (50 mug) or virgin female C. oregonensis suggested that synthetic pheromone baits could be developed for monitoring C. oregonensis populations in commercial Douglas-fir seed orchards.