3-萘-2-基氧基丙烷-1,2-二醇 | 34646-56-5

• 物质功能分类: 分析化学 - 对照品
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-萘-2-基氧基丙烷-1,2-二醇
• 英文名称: 3-(naphthalen-2-yloxy)propane-1,2-diol
• 英文别名: 3-[2]naphthyloxy-propane-1,2-diol；3-[2]Naphthyloxy-propan-1,2-diol；Glycerin-mono-β-naphthylaether；Dioxy-β-naphthoxy-propan；1,2-Propanediol, 3-(2-naphthyloxy)-；3-naphthalen-2-yloxypropane-1,2-diol
• CAS: 34646-56-5
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: VKXGYKMQYZFKAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-萘-2-基氧基丙烷-1,2-二醇 在 吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 1-acetoxy-3-(2-naphthyloxy)propan-2-one
  参考文献：
  名称：

  Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones

  摘要：

  A series of 1-acetoxy-3-aryloxypropan-2-ones la-m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00626-5
• 作为产物：
  描述：

  3-氯-1,2-丙二醇 、 2-萘酚 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以79%的产率得到3-萘-2-基氧基丙烷-1,2-二醇
  参考文献：
  名称：

  Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones

  摘要：

  A series of 1-acetoxy-3-aryloxypropan-2-ones la-m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00626-5

文献信息

• 1,2,3-Trimethoxypropane and Glycerol Ethers as Bio-Sourced Solvents from Glycerol. Synthesis by Solvent-Free Phase-Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations
  作者：Marc Sutter、Wissam Dayoub、Estelle Métay、Yann Raoul、Marc Lemaire

  DOI：10.1002/cctc.201300458

  日期：2013.10

  phase‐transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150 g scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95 %. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol

  1,2,3-三甲氧基丙烷（2），1-烷氧基-2,3-二甲氧基丙烷和1-芳氧基-2,3-二甲氧基丙烷在固相转移催化中得到了良好的收率和选择性。无机碱和铵盐作为相转移催化剂，无需其他溶剂。不需要加热，并且容易在大气压下以150g规模进行合成。准备2，甘油的转化完成，并且预期的甘油三甲醚的选择性高于95％。该产品在有机反应中用作溶剂，例如甘油和植物油之间的酯交换反应，有机金属反应（格氏和巴比尔型反应），碳-碳偶联反应（Suzuki，Sonogashira，Heck）以及在脱氢反应中的醚化反应中烷基化。溶剂显示出有趣的聚合物增溶性能。
• Heterogeneous Palladium-Catalyzed Synthesis of Aromatic Ethers by Solvent-Free Dehydrogenative Aromatization: Mechanism, Scope, and Limitations Under Aerobic and Non-Aerobic Conditions
  作者：Marc Sutter、Romain Lafon、Yann Raoul、Estelle Métay、Marc Lemaire

  DOI：10.1002/ejoc.201300485

  日期：2013.9

  derivatives and alcohols, both non-aromatic precursors, aryl ethers could be synthesized in good yields and with good selectivities in the presence of a catalytic amount of Pd/C, in one step, without added solvent, in a reaction vessel open to air. For less reactive substrates, the addition of 1-octene in a closed system under non-aerobic conditions improved the conversion. In addition, the catalyst could

  以环己酮衍生物和醇为原料，这两种非芳香族前体，芳醚可以在催化量的 Pd/C 存在下以良好的产率和良好的选择性在一个步骤中合成，无需添加溶剂，在打开的反应容器中空气。对于反应性较低的底物，在非有氧条件下在封闭系统中添加 1-辛烯可提高转化率。此外，催化剂可以循环多次使用，芳醚收率没有下降。该方法也用于四氢萘酮衍生物和多元醇。进行了几个反应以提出这种转化的机制。形成烯醇醚，然后进行脱氢反应似乎是该反应的关键步骤。
• n-Butyllithium-promoted regioselective elimination of vicinal bis-triflate having an adjacent ether oxygen
  作者：Noriki Kutsumura、Kota Shibuya、Hitoshi Yamaguchi、Takao Saito

  DOI：10.1016/j.tetlet.2017.09.036

  日期：2017.10

  Regioselective elimination of a vicinal bis-triflate having an adjacent ether oxygen functional group has been developed. Considered in the context of our studies of the regioselective elimination of vicinal dibromide, the key to the mechanism involves the electron-withdrawing inductive effect of the neighboring oxygen functional group. Aliphatic vinyl triflate was shown to be effective in Suzuki–Miyaura

  已经开发了区域选择性消除具有相邻的醚氧官能团的邻位双三氟甲磺酸酯。在我们关于选择性选择性去除邻位二溴化物的研究背景下考虑，该机制的关键涉及相邻氧官能团的吸电子诱导作用。与相应的脂肪族乙烯基溴化物相比，脂肪族三氟甲磺酸乙烯酯在Suzuki-Miyaura交叉偶联中被证明是有效的。
• Straightforward heterogeneous palladium catalyzed synthesis of aryl ethers and aryl amines via a solvent free aerobic and non-aerobic dehydrogenative arylation
  作者：Marc Sutter、Nicolas Sotto、Yann Raoul、Estelle Métay、Marc Lemaire

  DOI：10.1039/c2gc36776a

  日期：——

  Aryl ethers have been prepared from cyclohexanone derivatives and various alcohols in the presence of a catalytic amount of palladium on charcoal. The formation of an enol ether followed by an aerobic or non-aerobic dehydrogenation reaction, seem to be the key steps of this transformation. In addition, this new method was also adapted for the synthesis of arylamines.

  在催化量的炭上钯的存在下，环己酮衍生物和各种醇被制备成芳基醚。烯醇醚的形成以及随后的有氧或无氧脱氢反应似乎是这种转化的关键步骤。此外，这种新方法还可用于合成芳胺。
• Highly Regioselective Ring Opening of Epoxides with Polymer Supported Phenoxide and Naphthoxide Anions
  作者：B. Tamami、N. Iranpoor、R. Rezaei

  DOI：10.1081/scc-200026220

  日期：2004.1

  Abstract Amberlite IRA‐400 supported phenoxide and naphthoxide anions are easily prepared. These polymer supported reagents that are highly air stable are used for the regioselective ring opening reactions of different epoxides to give aryl ether alcohols in high yields under mild reaction conditions.

  摘要 Amberlite IRA-400 负载的苯氧化物和萘氧化物阴​​离子很容易制备。这些高度空气稳定的聚合物负载试剂用于不同环氧化物的区域选择性开环反应，在温和的反应条件下以高产率得到芳醚醇。