(1aS,2S,5S,7aR)-2-(tert-butyldimethylsiloxy)-5-propyl-1a,5,6,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione | 805325-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1aS,2S,5S,7aR)-2-(tert-butyldimethylsiloxy)-5-propyl-1a,5,6,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione
• 英文别名: (1aS,2S,5S,7aR)-2-[tert-butyl(dimethyl)silyl]oxy-5-propyl-2,5,6,7a-tetrahydro-1aH-oxireno[2,3-g]isochromene-3,7-dione
• CAS: 805325-80-8
• 化学式: C₁₈H₂₈O₅Si
• 分子量: 352.503
• InChiKey: BAQYYZHXMHOKHR-BLQKSXIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1aS,2S,5S,7aR)-2-(tert-butyldimethylsiloxy)-5-propyl-1a,5,6,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione 在 甲醇 、 DOWEX 50W-X₄ 作用下， 反应 24.0h， 以86%的产率得到(1aR,2S,5S,7aR)-2-hydroxy-5-propyl-1a,5,6,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione
  参考文献：
  名称：

  Stereoselective Total Synthesis of ent-EI-1941-2 and Epi-ent-EI-1941-2

  摘要：

  The first asymmetric total syntheses of ent-EI-1941-2 and epi-ent-EI-1941-2 have been accomplished, starting from a chiral epoxy iodoquinone 6, a key intermediate in our total syntheses of epoxyquinols A and B. A key step in the preparation of ent-EI-1941-2 is an intramolecular carboxypalladation via a 6-endo cyclization mode, followed by beta-hydride elimination, while carboxymercuration is a key step in the synthesis of epi-ent-EI-1941-2.

  DOI：

  10.1021/ol0481479
• 作为产物：
  描述：

  (1aS,2S,7S,7aS)-2-(tert-butyldimethylsiloxy)-7-hydroxy-5-propyl-1a,2,5,6,7,7a-hexahydro-3H-1,4-dioxa-cyclopropa[b]naphthalen-3-one 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 (1aS,2S,5S,7aR)-2-(tert-butyldimethylsiloxy)-5-propyl-1a,5,6,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione 、 (1aS,2S,5R,7aR)-2-(tert-butyldimethylsiloxy)-5-propyl-1a,5,6,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione
  参考文献：
  名称：

  Stereoselective Total Synthesis of ent-EI-1941-2 and Epi-ent-EI-1941-2

  摘要：

  The first asymmetric total syntheses of ent-EI-1941-2 and epi-ent-EI-1941-2 have been accomplished, starting from a chiral epoxy iodoquinone 6, a key intermediate in our total syntheses of epoxyquinols A and B. A key step in the preparation of ent-EI-1941-2 is an intramolecular carboxypalladation via a 6-endo cyclization mode, followed by beta-hydride elimination, while carboxymercuration is a key step in the synthesis of epi-ent-EI-1941-2.

  DOI：

  10.1021/ol0481479