1-甲基-1-十二烷醇 | 59812-98-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-甲基-1-十二烷醇
• 英文名称: (R)-(-)-tridecan-2-ol
• 英文别名: (R)-2-tridecanol；tridecan-2-ol；(R)-tridecan-2-ol；(R)-(-)-2-Tridecanol；(2R)-tridecan-2-ol
• CAS: 59812-98-5
• 化学式: C₁₃H₂₈O
• 分子量: 200.365
• InChiKey: HKOLRKVMHVYNGG-CYBMUJFWSA-N

物化性质

• 沸点：
  257.3±3.0 °C(Predicted)
• 密度：
  0.831±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1-甲基-1-十二烷醇 在 吡啶 作用下， 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：

  (+/-)-1,2-epoxytridecane 在 lithium aluminium tetrahydride 、 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 水 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 72.0h， 生成 1-甲基-1-十二烷醇
  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

文献信息

• Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane
  作者：Jun Guo、Jianhui Chen、Zhan Lu

  DOI：10.1039/c5cc01084e

  日期：——

  The highly enantioselective cobalt-catalyzed hydroboration reaction of aryl ketones with HBpin was developed using iminopyridine oxazoline ligands. Halides, amines, ethers, sulfides, esters and amides are well tolerated under the mild reaction conditions, demonstrating its synthetic advantage. Substituted diaryl ketones could also be hydroborated with high enantioselectivity.

  使用亚氨基吡啶恶唑啉配体开发了芳基酮与HBpin的高对映选择性钴催化的硼氢化反应。在温和的反应条件下，卤化物，胺，醚，硫化物，酯和酰胺具有良好的耐受性，证明了其合成优势。取代的二芳基酮也可以高对映选择性进行硼氢化。
• ENANTIOFACE-DIFFERENTIATING HYDROGENATION OF 2-ALKANONES OVER MODIFIED RANEY NICKEL
  作者：Tsutomu Osawa

  DOI：10.1246/cl.1985.1609

  日期：1985.11.5

  2-Octanone was hydrogenated over tartaric acid-NaBr-modified Raney nickel in the presence of pivalic acid at various temperatures. The hydrogenation at 50–60 °C gave the best result with regard to the optical yield. Almost 80% of the optical yields were attained in the hydrogenations of various 2-alkanones.

  在新戊酸的存在下，在不同温度下，2-辛酮在酒石酸-溴化钠改性的阮内镍上氢化。就光学产率而言，50-60°C 下的氢化反应最佳。几乎 80% 的光学产率是在各种 2-烷酮的氢化中获得的。
• PARA AMINO BENZOIC ACID BASED NANOTUBES
  申请人：Yadav Jhillu S.

  公开号：US20130052137A1

  公开（公告）日：2013-02-28

  The invention relates to nanotubes and processes for making them and intermediates of a drug moiety or its derivative/s as a structural moiety with side chain/s capable of promoting self aggregation. The side chain/s are mono or a multiple of alkyl chain/s that are substituted or unsubstituted capable of creating self aggregating assemblies. A p-amino benzoic acid (PABA) moiety or derivative as a structural moiety of 4-alkylamido-N-pyridin-2yl-benzamide with a lauric or stearic side chain. 4-alkylamido-N-pyridin-2yl-benzamide and 4-Amino-N-pyridine-2 yl-benzamide, N-(Pyridine-2-yl)-4-dodecanamido-benzamide and N-(Pyridin-2-yl)-4-stearamidobenzamide are intermediates useful for in vivo Conjugation of an active ingredient, illustrated by Rhodamine B. With Rhodamine B as an active ingredient, nano-tubes prepared with lauric side chain, which show red fluorescence and is useful for in vivo tracking.

  该发明涉及纳米管及其制备方法，以及药物基团或其衍生物的中间体作为结构基团，具有能够促进自聚集的侧链。这些侧链是单个或多个烷基链，可以是取代或未取代的，能够形成自聚集的组装体。一种对氨基苯甲酸(PABA)基团或其衍生物作为4-烷基氨基-N-吡啶-2-基苯甲酰胺的结构基团，具有月桂酸或硬脂酸侧链。4-烷基氨基-N-吡啶-2-基苯甲酰胺和4-氨基-N-吡啶-2-基苯甲酰胺，N-(吡啶-2-基)-4-十二烷酰基苯甲酰胺和N-(吡啶-2-基)-4-硬脂酰胺基苯甲酰胺是用于体内活性成分共轭的有用中间体，以罗丹明B为例。以罗丹明B为活性成分，用具有月桂酸侧链的纳米管制备，显示红色荧光，适用于体内追踪。
• 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％）。
• Studies on PPL Catalyzed Acetylation of 2-Alkanols: Its Application for the Synthesis of 2-Dodecanol and 2-Tridecyl Acetate, the Pheromones of<i>Crematogaster</i>Ants and<i>Drosophila mulleri</i>Flies
  作者：Anubha Sharma、Archana S. Pawar、Subrata Chattopadhyay

  DOI：10.1080/00397919608003858

  日期：1996.1

  Several aliphatic 2-alkanols with varying chain length has been efficiently resolved by their acetylation using vinyl acetate/PPL in diisopropyl ether. The effect of solvent polarity, position and type of unsaturation and chain length has been probed. This has led to more convenient synthesis of some insect pheromones.