1,3,5-戊三醇三(三甲基甲硅烷基)醚 | 74685-20-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 1,3,5-戊三醇三(三甲基甲硅烷基)醚
• 英文名称: 1,3,5-pentanetriol tris(trimethylsilyl) ether
• 英文别名: 3,9-Dioxa-2,10-disilaundecane, 2,2,10,10-tetramethyl-6-[(trimethylsilyl)oxy]-；1,5-bis(trimethylsilyloxy)pentan-3-yloxy-trimethylsilane
• CAS: 74685-20-4
• 化学式: C₁₄H₃₆O₃Si₃
• 分子量: 336.695
• InChiKey: YNSMTYZBPODAGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,5-戊三醇三(三甲基甲硅烷基)醚 在 sodium sulfide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 1,3,5-戊三醇
  参考文献：
  名称：

  硫化钠作为温和的选择性甲硅烷基化试剂

  摘要：

  醇的二苯基叔丁氧基甲硅烷基（即DPTBOS）衍生物在乙醇中被非水合硫化钠选择性裂解，反应顺序为：伯̃磺酰胺onda叔胺。相应吨丁基二和二苯基吨-丁基衍生物保持在这些条件下不受影响。

  DOI：

  10.1016/0040-4039(95)01549-3
• 作为产物：
  描述：

  1,4-戊二烯-3-醇 在 咪唑 、 盐酸 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 三氟甲磺酸三甲基硅酯 、 双氧水 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.5h， 生成 1,3,5-戊三醇三(三甲基甲硅烷基)醚
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019

文献信息

• Enantiodifferentiating transformation of prochiral 1,3,5-pentanetriols controlled by intramolecular van der Waals attractions
  作者：Toshiro Harada、Isao Wada、Jun-ji Uchimura、Atsushi Inoue、Sachi Tanaka、Akira Oku

  DOI：10.1016/s0040-4039(00)92049-5

  日期：1991.2

  Acetalization of prochiral 1,3,5-pentanetriol derivatives (5) with l-menthone proceeded enantioselectively (3.0-4.6:1) to give chiral spiroacetals (6) which can be utilized as versatile chiral building blocks.
• Harada, Toshiro; Inoue, Atsushi; Wada, Isao, Journal of the American Chemical Society, 1993, vol. 115, # 17, p. 7665 - 7674
  作者：Harada, Toshiro、Inoue, Atsushi、Wada, Isao、Uchimura, Jun-Ji、Tanaka, Sachi、Oku, Akira

  DOI：——

  日期：——
• Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols
  作者：Toshiro Harada、Hideaki Kurokawa、Yasuhiro Kagamihara、Sachi Tanaka、Atsushi Inoue、Akira Oku

  DOI：10.1021/jo00031a019

  日期：1992.2

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.
• Sodium sulphide as a mild and selective desilylating reagent
  作者：T. Schmittberger、D. Uguen

  DOI：10.1016/0040-4039(95)01549-3

  日期：1995.10

  diphenyl-t-butoxysilyl (i.e. DPTBOS) derivatives of alcohols are selectively cleaved by nonahydrated sodium sulphide in ethanol, the order of reactivity being: primarys̃econdary⪢tertiary. The corresponding t-butyldimethylsilyl and diphenyl-t-butylsilyl derivatives remain unaffected in these conditions.

  醇的二苯基叔丁氧基甲硅烷基（即DPTBOS）衍生物在乙醇中被非水合硫化钠选择性裂解，反应顺序为：伯̃磺酰胺onda叔胺。相应吨丁基二和二苯基吨-丁基衍生物保持在这些条件下不受影响。