Triethyl-[1,4,5,7,8-pentamethoxy-3-[[5-(2-phenylmethoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]methyl]naphthalen-2-yl]oxysilane | 908338-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Triethyl-[1,4,5,7,8-pentamethoxy-3-[[5-(2-phenylmethoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]methyl]naphthalen-2-yl]oxysilane
• 英文别名: triethyl-[1,4,5,7,8-pentamethoxy-3-[[5-(2-phenylmethoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]methyl]naphthalen-2-yl]oxysilane
• CAS: 908338-99-8
• 化学式: C₃₈H₄₇NO₈Si
• 分子量: 673.879
• InChiKey: VZNAXLCREMPHQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.91
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  86.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Triethyl-[1,4,5,7,8-pentamethoxy-3-[[5-(2-phenylmethoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]methyl]naphthalen-2-yl]oxysilane 在 盐酸 、 甲醇 作用下， 反应 3.0h， 以51 mg的产率得到3-[5-(2-benzyloxy-phenyl)-4,5-dihydro-isoxazol-3-ylmethyl]-1,4,5,7,8-pentamethoxy-naphthalen-2-ol
  参考文献：
  名称：

  Investigation of a Convergent Route to Purpuromycin:  Benzofuran Formation vs Spiroketalization

  摘要：

  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.

  DOI：

  10.1021/ol061112j
• 作为产物：
  描述：

  1,4-dihydroxy-5,6,8-trimethoxy-naphthalene-2,3-dicarboxylic acid dimethyl ester 在 咪唑 、 盐酸 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 硫酸 、 ammonium acetate 、 双氧水 、 硼酸 、 silica gel 、 potassium carbonate 、 戴斯-马丁氧化剂 、 异氰酸苯酯 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 、 丙酮 、 苯 为溶剂， 反应 86.75h， 生成 Triethyl-[1,4,5,7,8-pentamethoxy-3-[[5-(2-phenylmethoxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]methyl]naphthalen-2-yl]oxysilane
  参考文献：
  名称：

  Investigation of a Convergent Route to Purpuromycin:  Benzofuran Formation vs Spiroketalization

  摘要：

  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.

  DOI：

  10.1021/ol061112j

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.