1-(2-Nitroethyl)-2-phenylmethoxybenzene | 908292-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(2-Nitroethyl)-2-phenylmethoxybenzene
• CAS: 908292-04-6
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: MLAWLVIAULGSQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-Nitroethyl)-2-phenylmethoxybenzene 在 镍 氢气 、 硼酸 、 异氰酸苯酯 、 三乙胺 作用下， 以 甲醇 、 水 、 苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 1,4-bis(2-benzyloxyphenyl)-4-hydroxybutan-2-one
  参考文献：
  名称：

  紫杉醇双酚螺酮的聚合途径：螺酮缩合立体化学的氢键控制

  摘要：

  温和有效的[3 + 2]氧化氮/烯烃环加成反应使双酚灵酮的前体迅速收敛，这是天然产品红霉素家族独有的结构类型。另外，实现来自C4-OH的氢键控制紫霉素核心的立体化学的前提导致在螺缩酮化中适度的非对映异构控制。这些系统的光谱和X射线数据首次提供了紫霉素相对构型的信息。

  DOI：

  10.1016/j.tetlet.2006.05.044
• 作为产物：
  描述：

  2-苄氧基苯甲醛 在 sodium tetrahydroborate 、 ammonium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 1-(2-Nitroethyl)-2-phenylmethoxybenzene
  参考文献：
  名称：

  紫杉醇双酚螺酮的聚合途径：螺酮缩合立体化学的氢键控制

  摘要：

  温和有效的[3 + 2]氧化氮/烯烃环加成反应使双酚灵酮的前体迅速收敛，这是天然产品红霉素家族独有的结构类型。另外，实现来自C4-OH的氢键控制紫霉素核心的立体化学的前提导致在螺缩酮化中适度的非对映异构控制。这些系统的光谱和X射线数据首次提供了紫霉素相对构型的信息。

  DOI：

  10.1016/j.tetlet.2006.05.044

文献信息

• Investigation of a Convergent Route to Purpuromycin:  Benzofuran Formation vs Spiroketalization
  作者：Stephen P. Waters、Michael W. Fennie、Marisa C. Kozlowski

  DOI：10.1021/ol061112j

  日期：2006.7.1

  A mild and efficient [3+2] nitrile oxide/olefin cycloaddition allows coupling of the highly functionalized naphthalene and isocoumarin hemispheres of purpuromycin. A rationale of the inability of advanced keto alcohols to spirocyclize is presented based upon a systematic examination of the electronic factors present in these systems and suggests that the biosynthesis of purpuromycin does not proceed through open-chain intermediates.
• Preparation of β-phenylnitroethanes having electron-donating aryl substitution
  作者：Frederick A. Luzzio、Marek T. Wlodarczyk、Damien Y. Duveau、Juan Chen

  DOI：10.1016/j.tetlet.2007.07.098

  日期：2007.9

  beta-Phenyl-beta-hydroxynitroethanes having activating aryl substituents are treated with triethylsilane/trifluoroacetic acid under solventless conditions to give the corresponding phenyinitroethanes. Substrates having no aryl substituents or substituents that are only mildly activating or deactivating do not result in appreciable conversion to the title compounds. (c) 2007 Elsevier Ltd. All rights reserved.
• Alternative Spiroketalization Methods toward Purpuromycin: A Hemiketal Conjugate Addition Strategy and Use of an Electron-Rich Isocoumarin Precursor
  作者：Rakeshwar Bandichhor、Andrew N. Lowell、Marisa C. Kozlowski

  DOI：10.1021/jo200398v

  日期：2011.8.19

  Two methods are presented that were designed to circumvent the persistent problem of benzofuran formation and instead yield a spiroketal of the rubromycin family type. First, using an alternative disconnection, a hemiketal conjugate addition to a naphthaquinone electrophile was investigated. Synthesis of the requisite electrophile provided insight into the selective oxidation and functionalization of the naphthalene portion. Second, the electronic features of the isocoumarin ring system were adjusted, and the corresponding reactivity further supports the hypothesis that electron-rich isocoumarins are capable of spiroketalization. Robust, flexible syntheses from simple precursors were developed that allowed multiple reduced isocoumarins to be generated. Combined, the data presented herein give insight into the sensitivities of this family and illuminate other potential methods of spiroketalization. In addition, the convergent assembly of substrates containing different naphthaquinone and isocoumarin subunits highlights the utility of our 1,3-dipolar cycloaddition approach to generate analogs of these structures for SAR, as well as chemical reactivity studies.