(S)-1,2-epoxytridecane | 59829-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (S)-1,2-epoxytridecane
• 英文别名: (S)-2-Undecyloxirane；(2S)-2-undecyloxirane
• CAS: 59829-82-2
• 化学式: C₁₃H₂₆O
• 分子量: 198.349
• InChiKey: ZKAPVLMBPUYKKP-ZDUSSCGKSA-N

物化性质

• 沸点：
  125 °C(Press: 0.15 Torr)
• 密度：
  0.860±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1,2-epoxytridecane 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (R)-2-tridecanyl acetate
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1021005517389
• 作为产物：
  描述：

  1-十三烯 在 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 3.5h， 生成 (S)-1,2-epoxytridecane
  参考文献：
  名称：

  (+)-Crambescin B 脱羧化物的合成新策略

  摘要：

  (+)-Crambescin B 脱羧化物采用新的合成策略合成，比之前报道的最短方法缩短了 9 个步骤。我们通过 MTS 测定确定了其对神经元 HT22 细胞的细胞毒性和保护作用。观察到细胞活力以浓度依赖性方式降低，而没有细胞脱离或收缩。此外，该化合物还可以保护谷氨酸诱导的细胞死亡。

  DOI：

  10.1002/ejoc.202400176

文献信息

• Stereochemistry of Δ⁴dehydrogenation catalyzed by an ivy (Hedera helix) Δ⁹desaturase homolog
  作者：Amy E. Tremblay、Edward Whittle、Peter H. Buist、John Shanklin

  DOI：10.1039/b617942h

  日期：——

  The stereochemistry of palmitoyl-ACP Delta(4) desaturase-mediated dehydrogenation has been examined by tracking the fate of deuterium atoms located on stereospecifically monodeuterated substrates-(4S)- and (4R)-[4-(2)H(1)]-palmitoyl-ACP and (5S)- and (5R)-[5-(2)H(1)]-palmitoyl-ACP. It was found that the introduction of the (Z)-double bond between C-4 and C-5 of a palmitoyl substrate occurs with pro-R

  棕榈酰-ACP Delta（4）脱氢酶介导的脱氢的立体化学已通过追踪位于立体特异性单氘化底物-（4S）-和（4R）-[4-（2）H（1）]上的氘原子的命运进行了检查。 -棕榈酰-ACP和（5S）-和（5R）-[5-（2）H（1）]-棕榈酰-ACP。发现在棕榈酰基底物的C-4和C-5之间引入（Z）-双键与pro-R对映选择性一起发生，该结果与密切相关的同源-castor硬脂酰-ACP Delta获得的结果相匹配。 （9）去饱和酶。这些数据表明，尽管两种酶之间的区域选择性不同，但氢去除的立体化学仍得以保留。
• Synthesis of the enantiomers of 5-hexadecanolide, the pheromone of the queen of the oriental hornet, vespa orientalis,employing enzymic resolution of (±)-2-aminotridecanoic acid as the key-step
  作者：Kenji Mori、Tatsuya Otsuka

  DOI：10.1016/s0040-4020(01)96498-1

  日期：1985.1

  Optical resolution of(±)-2-chloroacetylaminotridecanoic acid with amino acylase gave (S)-2-aminotridecanoic add, which was converted into highly optically pure (S)-5-hexadecanolide (the pheromone of Vespa orientalls). Similarly (R)-2-chloroacetylammotridecanoic acid recovered after the enzymic hydrolysis yielded (R)-5-hexadecanolide. The existing methods for the preparation of the enantiomers of 5-hexadecanolide

  （±）-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。
• Chemoselective reduction of 2,3-epoxy tosylates with DIBAL-H as a general route to enantiomerically-enriched 1-tosyloxy-2-alkanols
  作者：J. Michael Chong、James Johannsen

  DOI：10.1016/0040-4039(94)85359-2

  日期：1994.9

  2,3-Epoxy tosylates may be reduced with DIBAL-H in CH2Cl2 or ether at −40 °C to 1-tosyloxy-2-alkanols in high (94–98%) yields.

  用DIBAL-H的CH 2 Cl 2溶液或乙醚在-40°C下可将2,3-环氧甲苯磺酸酯还原为1-甲苯磺酰氧基-2-链烷醇，产率高（94-98％）。
• Asymmetric synthesis of 5-hexadecanolide, pheromone of the queen of the Oriental hornet, Vespa orientalis
  作者：Sushil Raina、Vinod K. Singh

  DOI：10.1016/0040-4020(96)00095-6

  日期：1996.3

  An efficient asymmetric synthesis of 5-hexadecanolide from a chiral epoxide is described. Both the enantiomeric forms of the chiral epoxide are easily available from mannitol and ascorbic acid. The key step in the synthesis is the formation of δ-lactone from δ-hydroxy acetal using m-CPBA and BF3·OEt2.

  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。
• Synthesis and biological investigation of the β-thiolactone and β-lactam analogs of tetrahydrolipstatin
  作者：Sylvain Aubry、Geneviève Aubert、Thierry Cresteil、David Crich

  DOI：10.1039/c2ob06976h

  日期：——

  The synthesis of β-thiolactone and β-lactam analogs of tetrahydrolipstatin is described from a common late-stage β-lactone derivative. These analogs, and a cis-disubstituted β-lactone analog of tetrahydrolipstatin, were screened for activity against porcine pancreatic lipase and for inhibition of cell growth of a panel of four human cancer lines.

  β-硫代内酯和β-内酰胺类似物的合成 四氢他汀从常见的后期β-内酯衍生物描述了β-内酯。这些类似物和顺式二取代的β-内酯类似物四氢他汀筛选了针对猪胰脂肪酶的活性，并抑制了一组四个人类癌症细胞系的细胞生长。