(S)-(+)-tridecan-2-ol | 1653-31-2

• 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)-(+)-tridecan-2-ol
• 英文别名: (S)-(+)-2-tridecanol；(2S)-Tridecan-2-ol；(S)-tridecan-2-ol；(S)-2-Tridecanol；tridecan-2-ol
• CAS: 1653-31-2；59812-98-5；112711-14-5；101186-18-9
• 化学式: C₁₃H₂₈O
• 分子量: 200.365
• InChiKey: HKOLRKVMHVYNGG-ZDUSSCGKSA-N

物化性质

• 熔点：
  29-30°C
• 沸点：
  156-157°C 11mm
• 密度：
  0.83
• 闪点：
  156-157°C/11mm
• LogP：
  5.268 (est)

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

安全信息

• 安全说明：
  S24/25
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (S)-(+)-tridecan-2-ol 在 吡啶 作用下， 生成 (S)-(+)-1-methyldodecyl 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：

  (S)-(-)-5-p-toluenesulfonylpentane-2-ol 在 disodium hydrogenphosphate 、 正丁基锂 、 sodium amalgam 作用下， 生成 (S)-(+)-tridecan-2-ol
  参考文献：
  名称：

  Synthesis of (S)-(+)-parasorbic acid and (S)-(+)-2-tridecanol acetate: Bakers' yeast reductions of γ and δ ketosulfones

  摘要：

  DOI：

  10.1016/s0040-4039(00)97900-0

文献信息

• Chiral Surfactant-Type Catalyst for Asymmetric Reduction of Aliphatic Ketones in Water
  作者：Jiahong Li、Yuanfu Tang、Qiwei Wang、Xuefeng Li、Linfeng Cun、Xiaomei Zhang、Jin Zhu、Liangchun Li、Jingen Deng

  DOI：10.1021/ja308357y

  日期：2012.11.14

  A novel chiral surfactant-type catalyst is developed. Micelles formed in water by association of the catalysts themselves, and this was confirmed by TEM analyses. Asymmetric transfer hydrogenation of aliphatic ketones catalyzed by the chiral metallomicellar catalyst gave good to excellent conversions and remarkable stereoselectivities (up to 95% ee). Synergistic effects between the metal-catalyzed

  开发了一种新型手性表面活性剂型催化剂。通过催化剂本身的结合在水中形成胶束，这通过 TEM 分析得到证实。由手性金属胶束催化剂催化的脂肪族酮的不对称转移氢化具有良好到优异的转化率和显着的立体选择性（高达 95% ee）。金属催化中心与金属胶束中核心的疏水微环境之间的协同作用导致高对映选择性。
• 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。
• Enantioselective Synthesis of (<i>S</i>)-1-Methyldodecyl Acetate, a Pheromone of<i>Drosophila mulleri</i>, via (-)-Sparteine-Assisted Deprotonation of 1-Dodecanol
  作者：Folker Hintze、Dieter Hoppe

  DOI：10.1055/s-1992-26340

  日期：——

  The title compound was synthesized with 98 % ee by enantioselective lithiation and methylation of 1-dodecanol, employing a new protection/activation method for primary alcohols, followed by asymmetric deprotonation of the carbamate.

  该化合物通过对1-十二醇进行对映选择性锂化和甲基化合成，得到了98%的对映体过量，采用了一种新的初级醇保护/活化方法，随后进行了氨基甲酸酯的非对称去质子化反应。
• BETA-LACTONE COMPOUNDS
  申请人：Smith Jeffrey W.

  公开号：US20090124681A1

  公开（公告）日：2009-05-14

  The present invention provides compounds having the general structure A, or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and R 1 comprises at least one moiety selected from a group consisting of an alkyl, an alkenyl, an aryl, a heterocycle, hydroxyl, ester, amido, aldehyde, and a halogen.

  本发明提供具有一般结构A的化合物，或其药学上可接受的衍生物：其中R是烷基基团，R1包括至少一种从烷基、烯基、芳基、杂环、羟基、酯、酰胺、醛基和卤素组成的基团。