3-(6-methyl-2-pyridyl)-2-oxa-3-aza-bicyclo[2.2.1]hept-5-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(6-methyl-2-pyridyl)-2-oxa-3-aza-bicyclo[2.2.1]hept-5-ene
• 英文别名: (1R,4S)-3-(6-methylpyridin-2-yl)-2-oxa-3-azabicyclo[2.2.1]hept-5-ene
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: IOAHNRANARYQAB-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-(6-methyl-2-pyridyl)-2-oxa-3-aza-bicyclo[2.2.1]hept-5-ene 在 indium(III) triflate 作用下， 反应 6.5h， 以32%的产率得到1-(N-(6-methyl-2-pyridyl)-N-hydroxyamino)-2-methoxycyclopent-3-ene
  参考文献：
  名称：

  Regio- and Stereoselective Indium Triflate-Mediated Nucleophilic Ring-Opening Reactions of 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene Systems

  摘要：

  Indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems with alcohols and water were investigated. Reactions of [2.2.1] bicyclic systems gave anti-1,2-,anti-1,4- and syn-1.4-ring-opened products with moderate to excellent regio- and stereoselectivity. When [2.2.2] bicyclic systems were subjected to similar reaction conditions, only anti-1.2 and anti-1,4-ring-opened products were obtained.

  DOI：

  10.1021/jo9016343
• 作为产物：
  描述：

  2-氨基-6-甲基吡啶 在 (S)-(-)-5,5-双(二苯膦基)-4,4-双-1,3-苯并间二氧杂环戊烯 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 N-chlorosuccinimide-dimethylsulfide complex 作用下， 以 二氯甲烷 为溶剂， 反应 9.17h， 生成 3-(6-methyl-2-pyridyl)-2-oxa-3-aza-bicyclo[2.2.1]hept-5-ene
  参考文献：
  名称：

  催化、高度对映和非对映选择性亚硝基 Diels-Alder 反应

  摘要：

  本通讯介绍了使用亚硝基吡啶作为底物和铜作为催化剂以一致的高产率和高对映选择性提供亚硝基 Diels-Alder 加合物的研究。获得的 Diels-Alder 加合物很容易转化为相应的手性氨基醇，而不会损失对映选择性。

  DOI：

  10.1021/ja049849w

文献信息

• [EN] CATALTYTIC ASYMMETRIC HETERO DIELS-ALDER REACTION OF A HETEROAROMATIC C-NITROSO DIENOPHILE: A NOVEL METHOD FOR SYNTHESIS OF CHIRAL NON-RACEMIC AMINO ALCOHOLS<br/>[FR] REACTION HETERO DIELS-ALDER IMPLIQUANT UN DIENOPHILE C-NITROSO HETEROAROMATIQUE : NOUVEAU PROCEDE DE SYNTHESE D'AMINO-ALCOOLS NON RACEMIQUES CHIRAUX
  申请人：UNIV CHICAGO

  公开号：WO2005068457A1

  公开（公告）日：2005-07-28

  The present invention is directed to a catalytic asymmetric C-nitroso Diels-Alder reaction.

  本发明涉及一种催化不对称C-亚硝基Diels-Alder反应。
• Copper(<scp>i</scp>)/TF-BiphamPhos catalyzed asymmetric nitroso Diels–Alder reaction
  作者：Jun Li、Hai-Yan Tao、Chun-Jiang Wang

  DOI：10.1039/c6cc09587a

  日期：——

  A highly efficient enantioselective Nitroso Diels-Alder reactions of 6-methyl-2-nitroso pyridine with various 1,3-dienes were successfully developed with Cu(I)/(S)-TF-BiphamPhos complex as the catalyst. For most of the cyclic dienes, the synthetically...

  以Cu（I）/（S）-TF-BiphamPhos络合物为催化剂，成功开发了6-甲基-2-亚硝基吡啶与各种1,3-二烯的高效对映选择性亚硝基Diels-Alder反应。对于大多数环状二烯，合成...
• Retro iminonitroso Diels–Alder reactions: interconversion of nitroso cycloadducts
  作者：Baiyuan Yang、Weimin Lin、Viktor Krchnak、Marvin J. Miller

  DOI：10.1016/j.tetlet.2009.07.121

  日期：2009.10

  Retro iminonitroso Diels-Alder reactions were investigated in both solution and solid phase. In thermal or Cu(I)-mediated reactions, interconversion of various nitroso cycloadducts occurred in the presence of separate dienes. Up to 99% of conversion was observed. Use of chiral ligands in the Cu(I)-mediated reactions gave new cycloadducts enantioselectively. (C) 2009 Elsevier Ltd. All rights reserved.
• Catalytic, Highly Enantio, and Diastereoselective Nitroso Diels−Alder Reaction
  作者：Yuhei Yamamoto、Hisashi Yamamoto

  DOI：10.1021/ja049849w

  日期：2004.4.1

  This communication presents studies that nitroso Diels-Alder adduct has been furnished in uniformly high yield and high enantioselectivity using nitrosopyridine as a substrate and copper as a catalyst. The obtained Diels-Alder adduct was easily transformed to corresponding chiral amino alcohols without loss of enantioselectivity.

  本通讯介绍了使用亚硝基吡啶作为底物和铜作为催化剂以一致的高产率和高对映选择性提供亚硝基 Diels-Alder 加合物的研究。获得的 Diels-Alder 加合物很容易转化为相应的手性氨基醇，而不会损失对映选择性。
• Regio- and Stereoselective Indium Triflate-Mediated Nucleophilic Ring-Opening Reactions of 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene Systems
  作者：Baiyuan Yang、Marvin J. Miller

  DOI：10.1021/jo9016343

  日期：2009.10.16

  Indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems with alcohols and water were investigated. Reactions of [2.2.1] bicyclic systems gave anti-1,2-,anti-1,4- and syn-1.4-ring-opened products with moderate to excellent regio- and stereoselectivity. When [2.2.2] bicyclic systems were subjected to similar reaction conditions, only anti-1.2 and anti-1,4-ring-opened products were obtained.