(±)-2-hydroxydecyl tosylate | 111221-83-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (±)-2-hydroxydecyl tosylate
• 英文别名: 2-hydroxydecyl p-toluenesulfonate；2-Hydroxydecyl 4-methylbenzenesulfonate
• CAS: 111221-83-1
• 化学式: C₁₇H₂₈O₄S
• 分子量: 328.473
• InChiKey: UHMUNXMEITYUKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-2-hydroxydecyl tosylate 在 吡啶 、 lipase PS from Burkholderia cepacia 作用下， 以 aq. phosphate buffer 为溶剂， 反应 53.0h， 生成 (S)-2-acetoxydecyl tosylate
  参考文献：
  名称：

  Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion

  摘要：

  We have succeeded in accomplishing the deracemization of (+/-)-2-acetoxydecyl and (+/-)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-gamma-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.023
• 作为产物：
  描述：

  正癸烯 在 四氧化锇 、 水 、 二正丁基氧化锡 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.5h， 生成 (±)-2-hydroxydecyl tosylate
  参考文献：
  名称：

  Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion

  摘要：

  We have succeeded in accomplishing the deracemization of (+/-)-2-acetoxydecyl and (+/-)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-gamma-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.11.023

文献信息

• Montmorillonite Clay Catalyzed Tosylation of Alcohols and Selective Monotosylation of Diols with p-Toluenesulfonic Acid: An Enviro-Economic Route
  作者：Boyapati M. Choudary、Naidu S. Chowdari、Mannepalli L. Kantam

  DOI：10.1016/s0040-4020(00)00626-8

  日期：2000.9

  enviro-economic route for tosylation of alcohols and selective monotosylation of diols in good yield directly using p-toluenesulfonic acid together with metal-exchanged montmorillonite instead of p-toluenesulfonyl chloride or p-toluenesulfonic anhydride is described. The Fe3+-montmorillonite clay is the most effective catalyst among metal-exchanged montmorillonites for such tosylation reactions. The activity

  描述了直接使用对甲苯磺酸与金属交换的蒙脱石代替对甲苯磺酰氯或对甲苯磺酸酐以高产率直接进行醇的甲苯磺酸化和二醇的选择性单甲苯磺酸酯化的经济经济路线。Fe 3+-蒙脱石粘土是金属交换蒙脱石中对于这种甲苯磺酸化反应最有效的催化剂。活性遵循以下顺序：Fe 3+ > Zn 2+ > Cu 2+ > Al 3+-蒙脱石> K10蒙脱石。可以高纯度实现二醇的区域选择性甲苯磺酸化成单甲苯基化的衍生物。在同时具有伯羟基和仲羟基的二醇中，甲苯磺酰化仅在伯羟基上发生。固体催化剂在环己醇甲苯磺酸化中举例说明的几个循环中显示出一致的活性。
• [EN] PHEROMONES AND METHOD OF PREVENTING INFESTATION OF CONTARINIA NASTURTII<br/>[FR] PHEROMONES ET PROCEDE DE PREVENTION CONTRE L'INFESTATION DE CONTARINIA NASTURTII
  申请人：FORSKARPATENT I SYD AB

  公开号：WO2005077174A1

  公开（公告）日：2005-08-25

  The present invention relates to a pheromone mixture comprising 2,9­diacetoxyundecane, 2,10-diacetoxyundecane and 2-acetoxyundecane, as a racemate or, biologically active stereoisomers thereof, as well as a method for monitoring and/or mating disruption of swede midge, Contarinia nasturtii, in Brassica vegetables, in particular Brussels sprouts, cauliflower and broccoli.

  本发明涉及一种信息素混合物，包括2,9-双乙酰氧基十一烷、2,10-双乙酰氧基十一烷和2-乙酰氧基十一烷，作为其外消旋体或具有生物活性的立体异构体，以及一种用于监测和/或干扰甘蓝蚜虫Contarinia nasturtii在十字花科蔬菜，特别是花椰菜、西兰花和青花菜中的交配的方法。
• Reaction of Terminal Oxiranes With Arenesulfonic Acid
  作者：Kazuo Ogawa、Shunsaku Ohta、Masao Okamoto

  DOI：10.1055/s-1987-27918

  日期：——

  The reaction of oxiranes 1 with arenesulfonic acids under phase transfer catalyst system (water/dichloromethane) or without catalyst (dry dichloromethane) affords regioisomeric arylsulfonyloxy primary and secondary alcohols. The latter is oxidized to 1-arylsulfonyloxy-2-alkanones 5 in good yield.

  氧杂环1与芳基磺酸在相转移催化剂体系（水/二氯甲烷）或无催化剂（干二氯甲烷）条件下反应，生成区域异构的芳基磺酸氧烷基初级和次级醇。后者被氧化生成良好产率的1-芳基磺酸氧烷基-2-烷酮5。
• Pheromones and method of preventing infestation of Contarinia nasturtii
  申请人：Hillbur Ylva

  公开号：US20070122376A1

  公开（公告）日：2007-05-31

  The present invention relates to pheromone mixture comprising 2,9 diacetoxyundecane, 2,10-diacetoxyundecane and 2-acetoxyundecane, as a racemate or, biologically active stereoisomers thereof, as well as a method for monitoring and/or mating disruption of swede midge, Contarinia nasturtii, in Brassica vegetables, in particular Brussels sprouts, cauliflower and broccoli.

  本发明涉及一种信息素混合物，包括2,9-二乙酰氧基十一烷、2,10-二乙酰氧基十一烷和2-乙酰氧基十一烷，作为外消旋体或其生物活性立体异构体，以及一种用于监测和/或干扰芥菜蔬菜中的芥蚜（Contarinia nasturtii）交配的方法，特别是在芽甘蓝、花椰菜和西兰花中。
• PHEROMONES AND METHOD OF PREVENTING INFESTATION OF CONTARINIA NASTURTII
  申请人：Hillbur Ylva

  公开号：US20080219945A1

  公开（公告）日：2008-09-11

  The present invention relates to pheromone mixture comprising 2,9 diacetoxyundecane, 2,10-diacetoxyundecane and 2-acetoxyundecane, as a racemate or, biologically active stereoisomers thereof, as well as a method for monitoring and/or mating disruption of swede midge, Contarinia nasturtii , in Brassica vegetables, in particular Brussels sprouts, cauliflower and broccoli.

  本发明涉及一种信息素混合物，包括2,9-二乙酰氧基十一烷、2,10-二乙酰氧基十一烷和2-乙酰氧基十一烷，作为外消旋体或其生物活性立体异构体，以及一种用于监测和/或破坏甘蓝类蔬菜中的欧洲油蝇（Contarinia nasturtii）交配的方法，特别是在球芽甘蓝、花椰菜和西兰花中。