(4RS)-4,5-{[bis(1,1-dimethylethyl)silylene]dioxy}-3,4-dihydronaphthalen-1(2H)-one | 1172999-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (4RS)-4,5-{[bis(1,1-dimethylethyl)silylene]dioxy}-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: (3aRS)-2,2-bis(1,1-dimethylethyl)-4,5-dihydronaphtho[1,8-de]-1,3,2-dioxasilin-6(3aH)-one；3,3-Ditert-butyl-2,4-dioxa-3-silatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-trien-8-one
• CAS: 1172999-52-8
• 化学式: C₁₈H₂₆O₃Si
• 分子量: 318.488
• InChiKey: DHOMWLBUYJFDOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  di(tert-butyl)silylene ditriflate 、 (4RS)-4,5-{[bis(1,1-dimethylethyl)silylene]dioxy}-3,4-dihydronaphthalen-1(2H)-one 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.42h， 以92%的产率得到(1RS)-1,8-{[bis(1,1-dimethylethyl)silylene]dioxy}-4-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-1,2-dihydronaphthalene
  参考文献：
  名称：

  立体选择性合成顺式和反式-3,4-二氢-3,4,8-三羟基萘-1（2 H）-one

  摘要：

  Abstractmagnified imageA short and efficient protocol for the stereoselective synthesis of racemic trans‐ and cis‐3,4‐dihydro‐3,4,8‐trihydroxynaphthalen‐1(2H)‐one (1 and 2, resp.), is described, comprising nine and eight steps starting from commercial juglone (=5‐hydroxynaphthalene‐1,4‐dione; 12) (Scheme 4). Furthermore, an attempt to obtain 1 and 2 via phthalide annulation as the key step (Schemes 2 and 3) and a regioselective oxidation of the intermediate 1,2,3,4‐tetrahydronaphthalene‐1,2,4,5‐tetrols 27 and 28 with activated MnO2 were carried out (Scheme 4).

  DOI：

  10.1002/hlca.200800380
• 作为产物：
  描述：

  二叔丁基氯硅烷 、 4,5-dihydroxy-α-tetralone 在 1-羟基苯并三唑 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以83%的产率得到(4RS)-4,5-{[bis(1,1-dimethylethyl)silylene]dioxy}-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  立体选择性合成顺式和反式-3,4-二氢-3,4,8-三羟基萘-1（2 H）-one

  摘要：

  Abstractmagnified imageA short and efficient protocol for the stereoselective synthesis of racemic trans‐ and cis‐3,4‐dihydro‐3,4,8‐trihydroxynaphthalen‐1(2H)‐one (1 and 2, resp.), is described, comprising nine and eight steps starting from commercial juglone (=5‐hydroxynaphthalene‐1,4‐dione; 12) (Scheme 4). Furthermore, an attempt to obtain 1 and 2 via phthalide annulation as the key step (Schemes 2 and 3) and a regioselective oxidation of the intermediate 1,2,3,4‐tetrahydronaphthalene‐1,2,4,5‐tetrols 27 and 28 with activated MnO2 were carried out (Scheme 4).

  DOI：

  10.1002/hlca.200800380

文献信息

• Stereoselective Synthesis of<i>cis-</i>and<i>trans</i>-3,4-Dihydro-3,4,8-trihydroxynaphthalen-1(2<i>H</i>)-one
  作者：Emmanuel Couché、Abdellatif Fkyerat、Raffaele Tabacchi

  DOI：10.1002/hlca.200800380

  日期：2009.5

  Abstractmagnified imageA short and efficient protocol for the stereoselective synthesis of racemic trans‐ and cis‐3,4‐dihydro‐3,4,8‐trihydroxynaphthalen‐1(2H)‐one (1 and 2, resp.), is described, comprising nine and eight steps starting from commercial juglone (=5‐hydroxynaphthalene‐1,4‐dione; 12) (Scheme 4). Furthermore, an attempt to obtain 1 and 2 via phthalide annulation as the key step (Schemes 2 and 3) and a regioselective oxidation of the intermediate 1,2,3,4‐tetrahydronaphthalene‐1,2,4,5‐tetrols 27 and 28 with activated MnO2 were carried out (Scheme 4).