(1S,2S,4R)-3-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (1S,2S,4R)-3-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: ZZQYFYSMSNWWNS-HNACHXKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  环戊二烯 、 巴豆醛 在 硼烷四氢呋喃络合物 、 monacylated (2R,3R)-tartaric acid (1a) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (1S,2S,4R)-3-methylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde 、 3-methylbicyclo[2.2.1]oct-5-ene-2-carboxaldehyde
  参考文献：
  名称：

  Chiral (acyloxy)borane (CAB): a powerful and practical catalyst for asymmetric Diels-Alder reactions

  摘要：

  DOI：

  10.1021/jo00268a001

文献信息

• Design of chiral tin(IV) aryloxide as a mild Lewis acid catalyst for enantioselective Diels–Alder reaction
  作者：Taichi Kano、Teppei Konishi、Shunsuke Konishi、Keiji Maruoka

  DOI：10.1016/j.tetlet.2005.12.001

  日期：2006.2

  A novel Sn(IV) aryloxide Lewis acid has been designed and prepared from SnCl4 and (S)-3,3′-bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-bi-2-naphthol. The chiral Sn(IV) Lewis acid has been successfully applied to the enantioselective Diels–Alder reaction.

  由SnCl 4和（S）-3,3'-双（3,5-双（三氟甲基）苯基）-1,1'-bi-2-萘酚设计并制备了新型的Sn（IV）芳氧基路易斯酸。手性Sn（IV）路易斯酸已成功应用于对映选择性Diels-Alder反应。
• Enantioselective catalysts based on the chiral fragment (η5-C5Me5)Ir(Prophos) for Diels–Alder reactions
  作者：Daniel Carmona、Fernando Viguri、Ainara Asenjo、Fernando J. Lahoz、Pilar García-Orduña、Luis A. Oro

  DOI：10.1016/j.molcata.2014.01.021

  日期：2014.4

  The aqua complex (S-Ir,R-C)-[(eta(5)-C5Me5)Ir(Prophos)(H2O)][SbF6](2) [Prophos = (R)-propane-1,2-diyl-bis(diphenylphosphane)] is an active precursor for the asymmetric Diels-Alder reaction of acyclic enals with cyclopentadiene, 2,3-dimethylbutadiene and isoprene. Enantioselectivities up to 78% ee are achieved. The intermediate Lewis acid-dienophile complex (S-Ir,R-C)-[(eta(5)-C5Me5)Ir(Prophos)(ethyl acrolein)][SbF6](2) has been isolated and completely characterized, including the X-ray crystal structure determination. Structural parameters indicate that the disposition of the coordinated dienophile is controlled by CH/pi attractive interactions established between a phenyl group of the Prophos ligand and the aldehyde proton of the coordinated enal. Proton NMR data indicate that these interactions are maintained in solution. From diffractometric and spectroscopic data, the origin of the enantioselectivity is discussed. (C) 2014 Elsevier B.V. All rights reserved.
• Reusable montmorillonite-entrapped organocatalyst for asymmetric Diels–Alder reaction
  作者：Takato Mitsudome、Kenta Nose、Tomoo Mizugaki、Koichiro Jitsukawa、Kiyotomi Kaneda

  DOI：10.1016/j.tetlet.2008.07.011

  日期：2008.9

  A chiral organocatalyst was successfully entrapped by montmorillonite clay using the cation-exchange method. The mont-entrapped organocatalyst acted as a highly efficient and reusable heterogeneous catalyst for the asymmetric Diels-Alder reaction, without loss of its initial activity. (C) 2008 Elsevier Ltd. All rights reserved.