(1aR,2S,5R,7aR)-2-hydroxy-5-propyl-1a,2a,5,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione | 805325-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: (1aR,2S,5R,7aR)-2-hydroxy-5-propyl-1a,2a,5,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione
• CAS: 805325-83-1
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: LTZUXAJMSGNXOP-MHVFZMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  76.13
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1aR,2S,5R,7aR)-2-hydroxy-5-propyl-1a,2a,5,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以3.5 mg的产率得到(1aR,2S,5R,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,5R,6S,7aR)-2-(tert-butyldimethylsiloxy)-6-chloromercurio-5-propyl-1a,5,6,7a-tetrahydro-2H-1,4-dioxa-cyclopropa[b]naphthalene-3,7-dione 在 氟化氢吡啶 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.17h， 生成 (1aR,2S,5R,7aR)-2-hydroxy-5-propyl-1a,2a,5,7a-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