(1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-[(E)-pent-1-enyl]-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid | 805325-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-[(E)-pent-1-enyl]-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid
• 英文别名: (1S,2S,6R)-2-[tert-butyl(dimethyl)silyl]oxy-5-oxo-4-[(E)-pent-1-enyl]-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid
• CAS: 805325-65-9
• 化学式: C₁₈H₂₈O₅Si
• 分子量: 352.503
• InChiKey: XLNUIFFTBSAAMU-KYCPFSKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-[(E)-pent-1-enyl]-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid 在 二(氰基苯)二氯化钯 sodium tetrahydroborate 、 对苯醌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.33h， 生成 (1aS,2S,7R,7aS)-2-(tert-butyldimethylsiloxy)-7-hydroxy-5-propyl-1a,2,7,7a-tetrahydro-3H-1,4-dioxa-cyclopropa[b]naphthalen-3-one
  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：

  1-戊烯基硼酸 在 二(氰基苯)二氯化钯 三苯胂 、 三氟乙酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 (1S,2S,6R)-2-(tert-butyldimethylsiloxy)-5-oxo-4-[(E)-pent-1-enyl]-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid
  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

文献信息

• Stereoselective Total Synthesis of <i>ent</i>-EI-1941-2 and Epi-<i>ent</i>-EI-1941-2
  作者：Mitsuru Shoji、Takao Uno、Yujiro Hayashi

  DOI：10.1021/ol0481479

  日期：2004.11.1

  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.