(endo-methyl-2 bicyclo<2.2.1>heptene-5) yl-2 ethyl cetone | 51789-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (endo-methyl-2 bicyclo<2.2.1>heptene-5) yl-2 ethyl cetone
• 英文别名: endo-2-methyl-bicyclo<2.2.1>hept-5-en-2-yl ethyl ketone；endo-2-Methylbicyclo<2.2.1>hept-5-enyl ethyl ketone；(endo-methyl-2 bicyclo[2.2.1]heptene-5) yl-2 ethyl cetone；1-[(1R,2S,4R)-2-methyl-2-bicyclo[2.2.1]hept-5-enyl]propan-1-one
• CAS: 51789-57-2；51789-59-4；82815-02-9；119030-94-3
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: SSVNCQMQMXCFFR-YWVKMMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (endo-methyl-2 bicyclo<2.2.1>heptene-5) yl-2 ethyl cetone 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 exo (anti 1,2 syn-2,3 methyl-2 phenyl-3 propanediol-1,3 yl-1)-5 endo methyl-5 bicyclo<2.2.1>heptene-2
  参考文献：
  名称：

  Aldolisation stereocontrolee par un groupe thermolabile. Synthese stereoselective de composes possedant trois carbones asymetriques consecutifs

  摘要：

  DOI：

  10.1016/s0040-4020(01)81704-x
• 作为产物：
  描述：

  endo-bicyclo[2.2.1]hept-5-ene-2-methyl-2-carboxaldehyde 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 15.42h， 生成 (endo-methyl-2 bicyclo<2.2.1>heptene-5) yl-2 ethyl cetone
  参考文献：
  名称：

  Aldolisation stereocontrolee par un groupe thermolabile. Synthese stereoselective de composes possedant trois carbones asymetriques consecutifs

  摘要：

  DOI：

  10.1016/s0040-4020(01)81704-x

文献信息

• Mellor,J.M.; Webb,C.F., Journal of the Chemical Society. Perkin transactions II, 1974, p. 17 - 22
  作者：Mellor,J.M.、Webb,C.F.

  DOI：——

  日期：——
• Efficient and highly stereoselective syntheses of enantiomerically enriched C(1)-C(7) subunits of erythronolides
  作者：Mohammed Ahmar、Isabelle Romain、Robert Bloch

  DOI：10.1021/jo00063a009

  日期：1993.5

  Stereocontrolled efficient syntheses of the C(1)-C(7) fragments of deoxyerythronolide and erythronolide seco acids are described. The key step of these syntheses involves a highly stereoselective aldol condensation between an enantiomerically enriched 2-arylpropanal and the lithium enolate of the racemic 2-methyl-5-norbornenyl ethyl ketone, which establishes in one operation the relative and absolute configurations of the three stereocenters C(2), C(3), and C(4). After syn-selective reductions of the carbonyl group, the configuration required at carbon C(6) was introduced by highly selective reactions carried out on the double bond regenerated by a thermal cycloreversion.
• Endo-2-methyl-bicyclo[2.2.1]-hept-5enyl ethyl ketone: an useful and highly stereoselective synthon for aldol reactions
  作者：Mohammed Ahmar、Robert Bloch、Gérard Mandville、Isabelle Romain

  DOI：10.1016/s0040-4039(00)92225-1

  日期：1992.4

  An excellent aldehyde diastereofacial selectivity has been observed during the aldol condensation between the lithium enolate of endo-2-methyl-bicyclo[2.2.1]-hept-5-enyl ethyl ketone 1 and a variety of alpha-methyl chiral aldehydes. 2-Aryl- and 2-vinyl-propionaldehyde gave rise to the predicted syn, syn "Felkin-Anh" diastereoisomers. In contrast beta-alkoxy or beta-silyloxy alpha-methyl aldehydes lead to the syn, anti aldols arising from an apparent chelation control.
• BLOCH R.; GILBERT L., TETRAHEDRON LETT., 27,(1986) N 30, 3511-3514
  作者：BLOCH R.、 GILBERT L.

  DOI：——

  日期：——
• BLOCH, R.;GILBERT, L., TETRAHEDRON, 44,(1988) N 9, 2523-2539
  作者：BLOCH, R.、GILBERT, L.

  DOI：——

  日期：——