(1S,4S,7S)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester | 1239475-08-1

• 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: (1S,4S,7S)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester
• 英文别名: (1S,4S,7S)-phenyl 7-(hydroxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate；phenyl (1S,4S,7S)-7-(hydroxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate
• CAS: 1239475-08-1
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: IOJBFTNTEJJGRD-BZPMIXESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  氯甲酸苯酯 在 sodium tetrahydroborate 、 (5R)-2,2,3-三甲基-5-苯基甲基-4-咪唑啉酮盐酸盐 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 29.0h， 生成 (1S,4S,7S)-7-hydroxymethyl-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylic acid phenyl ester
  参考文献：
  名称：

  三溴化硼辅助手性磷酸催化剂用于 1,2-二氢吡啶的高对映选择性 Diels-Alder 反应

  摘要：

  BBr3-手性磷酸配合物是一种高效实用的路易斯酸辅助布朗斯台德酸 (LBA) 催化剂，用于促进 α-取代丙烯醛和 α-CF3 丙烯酸酯的对映选择性 Diels-Alder (DA) 反应。特别是，α-取代的丙烯醛与 1,2-二氢吡啶的 DA 反应得到了相应的具有高对映选择性的光学活性异奎宁环。此外，还展示了向吲哚生物碱、长春花碱和别花红素的关键中间体的转化。

  DOI：

  10.1021/jacs.5b08693

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）。
• A highly enantioselective Diels–Alder reaction of 1,2-dihydropyridine using a simple β-amino alcohol organocatalyst for a practical synthetic methodology of oseltamivir intermediate
  作者：Chonticha Suttibut、Yoshihito Kohari、Ko Igarashi、Hiroto Nakano、Masafumi Hirama、Chigusa Seki、Haruo Matsuyama、Koji Uwai、Nobuhiro Takano、Yuko Okuyama、Kenichi Osone、Mitsuhiro Takeshita、Eunsang Kwon

  DOI：10.1016/j.tetlet.2011.06.109

  日期：2011.9

  An easily prepared chiral amino alcohol catalyst was found to provide an efficient synthetic intermediate of oseltamivir with excellent chemical yield and enantioselectivity (up to 98% yield and up to 98% ee) in enantioselective Diels-Alder reactions of 1,2-dihydropylidines with acroleins. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.