(2S,10S)-undecane-2,10-diol | 862503-00-2

• 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: (2S,10S)-undecane-2,10-diol
• CAS: 862503-00-2
• 化学式: C₁₁H₂₄O₂
• 分子量: 188.31
• InChiKey: DCWOAQHULIMVPB-QWRGUYRKSA-N

物化性质

• 沸点：
  300.7±10.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  8
• 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：

  (2S,10S)-undecane-2,10-diol 在 polyacrylamide-bound Novozyme 435(R) 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 (2S,10S)-2,10-diacetoxyundecane
  参考文献：
  名称：

  Furanyl spiroketals as stereochemical relays in the synthesis of 1,9-anti diols: synthesis of insect pheromones

  摘要：

  A suite of spiroketal insect pheromones (15 and 17a-d) has been synthesised in good yield and with very high levels of diastereoselectivity via furanyl spiroketals. Remote asymmetric induction is achieved under thermodynamic control. The use of furanyl spiroketals as temporary scaffolds in the synthesis of 1,9-anti diols has been demonstrated with the synthesis of the swede midge pheromone (2S, 10S)-2, 10-diacetoxyundecane 1. The enzymatic resolution of a C-2 symmetric 1,9-anti diol was used as a confirmation of diastereomeric purity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.004
• 作为产物：
  描述：

  丁位己内酯 在 ruthenium trichloride 、 镍 sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 生成 (2S,10S)-undecane-2,10-diol
  参考文献：
  名称：

  Furanyl spiroketals as stereochemical relays in the synthesis of 1,9-anti diols: synthesis of insect pheromones

  摘要：

  A suite of spiroketal insect pheromones (15 and 17a-d) has been synthesised in good yield and with very high levels of diastereoselectivity via furanyl spiroketals. Remote asymmetric induction is achieved under thermodynamic control. The use of furanyl spiroketals as temporary scaffolds in the synthesis of 1,9-anti diols has been demonstrated with the synthesis of the swede midge pheromone (2S, 10S)-2, 10-diacetoxyundecane 1. The enzymatic resolution of a C-2 symmetric 1,9-anti diol was used as a confirmation of diastereomeric purity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.004

文献信息

• [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。
• Palladium(II)-Catalyzed Enantioselective Hydrooxygenation of Unactivated Terminal Alkenes
  作者：Xintuo Yang、Xiang Li、Pinhong Chen、Guosheng Liu

  DOI：10.1021/jacs.2c02753

  日期：2022.5.11

  A novel Pd(II)-catalyzed enantioselective Markovnikov hydrooxygenation of unactivated terminal alkenes using a substituted pyridinyl oxazoline (Pyox) ligand has been developed. Herein it was discovered that the (EtO)2MeSiH/BQ redox system is vital for the highly selective and efficient hydrooxygenation, where the alkylpalladium(II) species generated from enantioselective oxypalladation step is reduced

  已经开发了一种使用取代的吡啶基恶唑啉 (Pyox) 配体对未活化末端烯烃进行新型 Pd(II) 催化的对映选择性马尔科夫尼科夫加氢氧化反应。在此发现 (EtO) 2 MeSiH/BQ 氧化还原系统对于高选择性和高效的加氢氧化至关重要，其中对映选择性氧化钯化步骤产生的烷基钯 (II) 物质被硅烷还原。该方法提供了从易于获得的烯烃中高效获得光学纯醇酯的方法，具有优异的对映选择性，并具有广泛的底物范围。
• 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。
• US7608254B2
  申请人：——

  公开号：US7608254B2

  公开（公告）日：2009-10-27