(5S)-5-({[Tri(propan-2-yl)silyl]oxy}methyl)oxolan-2-one | 189516-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5S)-5-({[Tri(propan-2-yl)silyl]oxy}methyl)oxolan-2-one
• 英文别名: (5S)-5-[tri(propan-2-yl)silyloxymethyl]oxolan-2-one
• CAS: 189516-38-9
• 化学式: C₁₄H₂₈O₃Si
• 分子量: 272.46
• InChiKey: LJAJSNNKLUOKPV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  (5S)-5-({[Tri(propan-2-yl)silyl]oxy}methyl)oxolan-2-one 在 Wilkinson's catalyst 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Study of butyrolactones related to sub-type 3 annonaceous acetogenins. Structure revision of itrabin, jetein, laherradurin and otivarin

  摘要：

  Starting from 5(S)-hydroxymethyl-gamma-butyrolactone 1, lactones related to title acetogenins have been prepared in few steps. This study leads to a structure revision of the lactone configurations of these acetogenins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01786-9
• 作为产物：
  描述：

  (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 、 三异丙基氯硅烷 以91%的产率得到(5S)-5-({[Tri(propan-2-yl)silyl]oxy}methyl)oxolan-2-one
  参考文献：
  名称：

  Study of butyrolactones related to sub-type 3 annonaceous acetogenins. Structure revision of itrabin, jetein, laherradurin and otivarin

  摘要：

  Starting from 5(S)-hydroxymethyl-gamma-butyrolactone 1, lactones related to title acetogenins have been prepared in few steps. This study leads to a structure revision of the lactone configurations of these acetogenins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01786-9

文献信息

• Novel synthesis of the indolizidine alkaloid skeleton with appropriate functionality and stereochemistry for use as a ‘chiral scaffold’
  作者：Elizabeth Farrant、John Mann

  DOI：10.1039/a701193h

  日期：——

  A stereocontrolled synthesis of the indolizidine alkaloid skeleton has been achieved via an intramolecular, photoinduced reaction of (5S)-5-triisopropylsilyloxymethyl-3-2′ -[(3″S)-3″ -methoxypyrrolidinyl]ethyl}furan-2-(5H)-one, which can be obtained in a highly convergent fashion from (5S)-5-triisopropylsilyloxymethyltetrahydrofuran-2-one and (3S)-3-methoxypyrrolidine.

  通过（5S）-5-三异丙基硅氧甲基-3-2²-[(3S)-3-甲氧基吡咯烷基]乙基}呋喃-2-(5H)-酮的分子内光诱导反应，实现了吲哚生物碱类分子骨架的立体控制合成，该反应可通过高度聚合的方式从（5S）-5-三异丙基硅氧甲基四氢呋喃-2-酮和（3S）-3-甲氧基吡咯烷获得。
• Study of butyrolactones related to sub-type 3 annonaceous acetogenins. Structure revision of itrabin, jetein, laherradurin and otivarin
  作者：Erwin Warmerdam、Isabelle Tranoy、Brigitte Renoux、Jean-Pierre Gesson

  DOI：10.1016/s0040-4039(98)01786-9

  日期：1998.10

  Starting from 5(S)-hydroxymethyl-gamma-butyrolactone 1, lactones related to title acetogenins have been prepared in few steps. This study leads to a structure revision of the lactone configurations of these acetogenins. (C) 1998 Elsevier Science Ltd. All rights reserved.