[2R]-Benzyl 2-methyl-4-penten-1-yl ether | 190005-22-2

• 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: [2R]-Benzyl 2-methyl-4-penten-1-yl ether
• 英文别名: {[(2-Methylpent-4-EN-1-YL)oxy]methyl}benzene；2-methylpent-4-enoxymethylbenzene
• CAS: 190005-22-2
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: VHNLFGSJUMRTMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [2R]-Benzyl 2-methyl-4-penten-1-yl ether 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 氢气 、 叔丁基锂 、 potassium carbonate 、 戴斯-马丁氧化剂 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 生成 1,11,16-Trihydroxy-3,7,11,15-tetramethylhexadecan-4-one
  参考文献：
  名称：

  Synthesis and biological activity of a stereoisomeric mixture of the mating hormone of Phytophthora

  摘要：

  The first synthesis of a stereoisomeric mixture of hormone alpha 1 the mating hormone of Phytophthora, was achieved, and the synthetic mixture was confirmed to be hormonally active. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.109
• 作为产物：
  描述：

  ((1R,2R)-2-Vinyl-cyclopropylmethoxymethyl)-benzene 在 zirconocene dichloride 、 正丁基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以56%的产率得到[2R]-Benzyl 2-methyl-4-penten-1-yl ether
  参考文献：
  名称：

  Complexation of Vinylcyclopropanes with Zirconocene−1-butene Complex:  Application to the Stereocontrolled Synthesis of Steroidal Side Chains

  摘要：

  Reactions of vinylcyclopropane derivatives with a zirconocene-1-butene complex (''Cp2Zr'') caused regioselective cleavage of the cyclopropyl bond to give eta(3) pi-allylic and/or eta(1) sigma-allylic complexes. The regioselectivity of the bond cleavage and the formation of a eta(3) pi-allylic or eta(1) sigma-allylic complex depend on the bulkiness of the substituents on the cyclopropyl group and the presence of leaving functionality. A catalytic use of ''Cp2Zr'' in the presence of excess Grignard reagent also caused a ring opening of the vinylcyclopropane derivatives with the same sense of regiochemical selectivity. The reaction of the thermally equilibrated ''Cp2Zr''-propenylcyclopropane complex with acetone indicated the possibility for the synthesis of the steroidal side chain in either natural or unnatural forms. The synthetic utility of the present ''Cp2Zr''-vinylcyclopropane chemistry was ascertained by the stereocontrolled preparation of the C-20, C-24 dimethylated steroidal side chain which is identical to the active metabolite of vitamin D-2.

  DOI：

  10.1021/jo962064r

文献信息

• In Situ Generated Bulky Palladium Hydride Complexes as Catalysts for the Efficient Isomerization of Olefins. Selective Transformation of Terminal Alkenes to 2-Alkenes
  作者：Delphine Gauthier、Anders T. Lindhardt、Esben P. K. Olsen、Jacob Overgaard、Troels Skrydstrup

  DOI：10.1021/ja9108424

  日期：2010.6.16

  enriched substrates provided products without epimerization at the allylic stereogenic carbon centers. Finally, some mechanistic investigations were undertaken to understand the nature of the active in situ generated Pd-H catalyst. These studies revealed that the catalytic system is highly dependent on the large steric demand of the P(tBu)(3) ligand. The use of an alternative ligand, cataCXium PinCy, also

  应用从 Pd(dba)(2)、P(tBu)(3) 和异丁酰氯的 1:1:1 混合物中获得的原位生成的大块钯 (II) 氢化物催化剂为异构化和多种烯烃的迁移。除了 (Z)- 到 (E)-烯烃的异构化之外，烯丙基苯、烯丙基醚和胺的共轭迁移以接近定量的产率和优异的官能团耐受性有效实现。通常使用 0.5-1.0 mol% 的催化剂负载量，但当反应在纯净条件下进行时，甚至可以实现低至 0.25 mol% 的负载量。更有趣的是，所研究的催化剂证明对将末端烯烃转化为 2-烯烃具有选择性。这种单取代烯烃的单碳迁移过程提供了一种替代催化剂，它弥合了烯丙基化和丙烯酰化/乙烯基化协议之间的差距。几种底物，包括高烯丙醇和胺，被选择性地转化为它们相应的 2-烯烃，使用对映体富集底物的例子提供了在烯丙基立体碳中心没有差向异构化的产物。最后，进行了一些机理研究以了解活性原位生成的 Pd-H 催化剂的性质。这些研究表明，催化系统高度依赖于
• [EN] SUBSTITUTED PYRAZOLOAZEPIN-8-ONES AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS<br/>[FR] PYRAZOLOAZÉPIN-8-ONES SUBSTITUÉES, ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA PHOSPHODIESTÉRASE
  申请人：LEO PHARMA AS

  公开号：WO2018108231A1

  公开（公告）日：2018-06-21

  The present invention relates to novel pyrazoloazepin-8-ones with phosphodiesterase inhibitory activity, as well as to their use as therapeutic agents in the treatment of inflammatory diseases and conditions.

  本发明涉及具有磷酸二酯酶抑制活性的新型吡唑啉-8-酮化合物，以及它们作为治疗炎症性疾病和症状的治疗剂的用途。
• FK-506 C10-C18 process intermediates
  申请人：Merck & Co., Inc.

  公开号：US05155228A1

  公开（公告）日：1992-10-13

  A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.18 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.

  本文描述了一种改进的合成过程，用于合成免疫抑制剂FK-506的大环内酯结构的光学纯C.sub.10-C.sub.18片段。该化合物还可用作制备FK-506衍生物的中间体。
• Process for synthesis of FK-506 C10-C18 intermediates
  申请人：Merck & Co., Inc.

  公开号：US04940797A1

  公开（公告）日：1990-07-10

  A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.18 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.

  描述了一种改进的合成过程，用于合成免疫抑制剂FK-506的大环结构中的光学纯度为C.sub.10 -C.sub.18的片段。该化合物还可作为制备FK-506衍生物的中间体。
• Oxazole derivatives and intermediates for their preparation
  申请人：MERCK & CO. INC.

  公开号：EP0398474A2

  公开（公告）日：1990-11-22

  A process is described for the improved synthesis of the optically pure C₁₀-C₁₈ fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.

  本研究描述了一种改进的工艺，用于合成免疫抑制剂 FK-506 的大环内酯结构的光学纯 C₁₀-C₁₈ 片段。该化合物还可用作制备 FK-506 衍生物的中间体。