tert-butyl-[1-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-2-nitroethoxy]dimethylsilane | 1315508-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl-[1-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-2-nitroethoxy]dimethylsilane
• 英文别名: Tert-butyl-dimethyl-[2-nitro-1-[5,6,8-trimethoxy-3,4-bis(phenylmethoxy)naphthalen-2-yl]ethoxy]silane
• CAS: 1315508-02-1
• 化学式: C₃₅H₄₃NO₈Si
• 分子量: 633.814
• InChiKey: GVTMIHZHSATSBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.36
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl-[1-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-2-nitroethoxy]dimethylsilane 在 氢气 、 硼酸 、 异氰酸对硝基苯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 15.0h， 生成 Methyl 6-[4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxy-3-oxo-4-[5,6,8-trimethoxy-3,4-bis(phenylmethoxy)naphthalen-2-yl]butyl]-1-oxo-7,8-bis(phenylmethoxy)isochromene-3-carboxylate
  参考文献：
  名称：

  Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation

  摘要：

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.

  DOI：

  10.1021/jo200399z
• 作为产物：
  描述：

  ethyl 3,4-dihydro-5,6,8-trimethoxy-3,4-dioxonaphthalene-2-carboxylate 在 lithium aluminium tetrahydride 、 正丁基锂 、 sodium dithionite 、 水 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 75.58h， 生成 tert-butyl-[1-(3,4-dibenzyloxy-5,6,8-trimethoxynaphthalen-2-yl)-2-nitroethoxy]dimethylsilane
  参考文献：
  名称：

  Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation

  摘要：

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.

  DOI：

  10.1021/jo200399z

文献信息

• Alternative Spiroketalization Methods toward Purpuromycin: A Diketone Approach To Prevent Benzofuran Formation
  作者：Andrew N. Lowell、Michael W. Fennie、Marisa C. Kozlowski

  DOI：10.1021/jo200399z

  日期：2011.8.19

  The central portion of purpuromycin has been assembled via a classical spiroketalization reaction. Key to promoting this reaction mode versus benzofuran formation was the oxidation state of the spiroketal core. With a higher oxidation state, even the electron-deficient isocoumarin found in purpuromycin could be employed directly in the spiroketalization. The two halves of the spiroketalization precursor were joined via a nitrile oxide/styrene 1,3-dipolar cycloaddition. A very mild selenium dioxide oxidation was used to introduce the required oxidation state of the spiroketal core.