4-[Tert-butyl(dimethyl)silyl]oxyoxane-2,6-diol | 459870-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-[Tert-butyl(dimethyl)silyl]oxyoxane-2,6-diol
• CAS: 459870-97-4
• 化学式: C₁₁H₂₄O₄Si
• 分子量: 248.395
• InChiKey: UMBDREJNEQODLI-UHFFFAOYSA-N

物化性质

• 沸点：
  313.7±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[Tert-butyl(dimethyl)silyl]oxyoxane-2,6-diol 在 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到3-((tert-butyldimethylsilyl)oxy)pentanedial
  参考文献：
  名称：

  Desymmetrisation of dialdehydes: (+)-(S) and (−)-(R) nor-methyl mevaldate as versatile synthetic intermediates

  摘要：

  DOI：

  10.1016/s0040-4039(02)00533-6
• 作为产物：
  描述：

  1,6-庚二烯-4-醇 在 咪唑 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 64.42h， 生成 4-[Tert-butyl(dimethyl)silyl]oxyoxane-2,6-diol
  参考文献：
  名称：

  nor-Mevaldic acid surrogates as selective antifungal agent leads against Botrytis cinerea. Enantioselective preparation of 4-hydroxy-6-(1-phenylethoxy)tetrahydro-2H-pyran-2-one

  摘要：

  Solvent-free desymmetrisation of meso-dialdehyde 1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one (+)-3a with a 96: 4 dr Deprotected lactone (+)-19a and the related racemic lactones 16a-18a present a lactone moiety resembling the natural substrate of HMG-CoA reductase and their antifungal properties have been evaluated against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides. These compounds were selectively active against B. cinerea, while inactive against C. gloeosporioides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.048

文献信息

• Desymmetrisation of dialdehydes: (+)-(S) and (−)-(R) nor-methyl mevaldate as versatile synthetic intermediates
  作者：Shirley L.J. Buckley、Michael G.B. Drew、Laurence M. Harwood、Antonio J. Macı́as-Sánchez

  DOI：10.1016/s0040-4039(02)00533-6

  日期：2002.5
• nor-Mevaldic acid surrogates as selective antifungal agent leads against Botrytis cinerea. Enantioselective preparation of 4-hydroxy-6-(1-phenylethoxy)tetrahydro-2H-pyran-2-one
  作者：José Manuel Botubol-Ares、María Jesús Durán-Peña、Rosario Hernández-Galán、Isidro G. Collado、Laurence M. Harwood、Antonio J. Macías-Sánchez

  DOI：10.1016/j.bmc.2015.04.048

  日期：2015.7

  Solvent-free desymmetrisation of meso-dialdehyde 1 with chiral 1-phenylethan-1-ol, led to preparation of 4-silyloxy-6-alkyloxytetrahydro-2H-pyran-2-one (+)-3a with a 96: 4 dr Deprotected lactone (+)-19a and the related racemic lactones 16a-18a present a lactone moiety resembling the natural substrate of HMG-CoA reductase and their antifungal properties have been evaluated against the phytopathogenic fungi Botrytis cinerea and Colletotrichum gloeosporioides. These compounds were selectively active against B. cinerea, while inactive against C. gloeosporioides. (C) 2015 Elsevier Ltd. All rights reserved.