phenyl (1S,4S,7R)-7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate | 1333309-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: phenyl (1S,4S,7R)-7-formyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate
• CAS: 1333309-65-1
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: CQMDRPQVBUWHIS-DYEKYZERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(phenoxycarbonyl)-1,2-dihydropyridine 、 丙烯醛 在 (S)-1,3-dihydroxy-1,1-diphenylpropan-2-aminium trifluoroacetate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以83%的产率得到
  参考文献：
  名称：

  Enantioselective Diels–Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst

  摘要：

  The enantioselective Diels Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active beta-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.

  DOI：

  10.1021/jo501433c

文献信息

• A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine
  作者：Hiroto Nakano、Kenichi Osone、Mitsuhiro Takeshita、Eunsang Kwon、Chigusa Seki、Haruo Matsuyama、Nobuhiro Takano、Yoshihito Kohari

  DOI：10.1039/c0cc00110d

  日期：——

  Enantioselective Diels–Alder reactions of 1,2-dihydropyridines with acroleins using a novel chiral oxazolidine organocatalyst afforded chiral isoquinuclidines that is an efficient synthetic intermediate of oseltamivir, with fairly good chemical yield and excellent enantioselectivity (90%, up to >99% ee).

  使用一种新型手性噁唑啉有机催化剂，通过1,2-二氢吡啶与丙烯醛的对映选择性Diels-Alder反应，合成了作为奥司他韦高效合成中间体的对映选择性异喹啉化合物，具有相当好的化学产率和极高的对映选择性（90%，高达>99% 对映体过量）。
• CHIRAL PRIMARY AMINO SILYL ETHER ORGANOCATALYST FOR THE ENANTIOSELECTIVE DIELS-ALDER REACTION OF 1,2-DIHYDROPYRIDINES WITH AlDEHYDES
  作者：Hiroto Nakano、Yuki Sakuta、Yoshihito Kohari、N. D. M. Romauli Hutabarat、Koji Uwai、Eunsang Kwon、Yuko Okuyama、Chigusa Seki、Haruo Matsuyama、Nobuhiro Takano、Michio Tokiwa、Mitsuhiro Takeshita

  DOI：10.3987/com-12-s(n)93

  日期：——

  The enantioselective Diels-Alder reactions of 1,2-dihydropyridines with acroleins using a chiral primary amino silyl ether organocatalyst afforded chiral isoquinuclidines with good chemical yields and excellent enantioselectivities (up to 70% and up to 99% ee).
• Enantioselective Diels–Alder Reaction of 1,2-Dihydropyridines with Aldehydes Using β-Amino Alcohol Organocatalyst
  作者：Yoshihito Kohari、Yuko Okuyama、Eunsang Kwon、Taniyuki Furuyama、Nagao Kobayashi、Teppei Otuki、Jun Kumagai、Chigusa Seki、Koji Uwai、Gang Dai、Tatsuo Iwasa、Hiroto Nakano

  DOI：10.1021/jo501433c

  日期：2014.10.17

  The enantioselective Diels Alder reaction of 1,2-dihydropyridines with aldehydes using an easily prepared optically active beta-amino alcohol catalyst was found to provide optically active isoquinuclidines, an efficient synthetic intermediate of pharmaceutically important compounds such as oseltamivir phosphate, with a satisfactory chemical yield and enantioselectivity (up to 96%, up to 98% ee). In addition, the obtained highly optically pure isoquinuclidine was easily converted to an optically active piperidine having four successive carbon centers.