N-phenoxycarbonyl-1,2,5,6-tetrahydropyridine | 203259-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenoxycarbonyl-1,2,5,6-tetrahydropyridine
• 英文别名: phenyl 3,6-dihydro-2H-pyridine-1-carboxylate
• CAS: 203259-90-9
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: WXJMRMQMWQAFDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  55.9-56.7 °C
• 沸点：
  311.4±35.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenoxycarbonyl-1,2,5,6-tetrahydropyridine 在 palladium on activated charcoal 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 反应 48.0h， 以94%的产率得到phenyl 3,4-dihydro-1(2H)-pyridinecarboxylate
  参考文献：
  名称：

  Reactivity of 2-cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic acid esters towards various nucleophiles: Regio- and stereoselectivity of the attack

  摘要：

  The synthesis and reactivity of the title compounds towards nucleophiles are discussed. The regio-and diastereoselectivity of the attack is highly dependent on the carbamic ester and the type of nucleophile applied. Both Michael type addition across the activated double bond and S(N)2T reaction at the carbamate carbon atom were observed. Structure assignment of the adducts in solution and in the solid state was performed utilizing high temperature NMR techniques as well as single crystal X-ray diffraction.

  DOI：

  10.1007/bf00806971
• 作为产物：
  描述：

  1,2,3,6-四氢吡啶 、 氯甲酸苯酯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 以67.9%的产率得到N-phenoxycarbonyl-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Engineered P450pyr monooxygenase for asymmetric epoxidation of alkenes with unique and high enantioselectivity

  摘要：

  P450pyr单加氧酶的三重突变体（P450pyrTM）作为首个展现出高（R）对映选择性和高转化率的酶，催化了几种对位取代苯乙烯的环氧化反应，其底物范围广泛，并对非共轭的1,1-二取代烯烃——2-甲基-3-苯基-1-丙烯，以及环烯烃——N-苯氧羰基-1,2,5,6-四氢吡啶的环氧化反应表现出高对映选择性。

  DOI：

  10.1039/c3cc46675b

文献信息

• ISOQUINUCLIDINE DERIVATIVE AND METHOD FOR PRODUCING 1-CYCLOHEXENE-1-CARBOXYLIC ACID DERIVATIVE BY USING THE SAME
  申请人：The University of Tokyo

  公开号：EP2050752A1

  公开（公告）日：2009-04-22

  The present invention provides an isoquinuclidine derivative which can be used to easily synthesize oseltamivir or an analog thereof. In particular, the present invention provides an isoquinuclidine derivative represented by the following formula (1) or an enantiomer thereof: wherein in the formula (1), A represents a protective group for the nitrogen atom; R1 to R1 each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom; and X represents a halogen atom.

  本发明提供了一种异喹啉衍生物，可用于轻松合成奥司他韦或其类似物。具体而言，本发明提供了由以下式（1）表示的异喹啉衍生物或其对映体： 在式（1）中，A代表氮原子的保护基团；R1到R1分别独立地代表可能具有取代基的烷基基团，可能具有取代基的芳基基团，或氢原子；X代表卤素原子。
• Enantioselective Trans Dihydroxylation of Nonactivated C−C Double Bonds of Aliphatic Heterocycles with <i>Sphingomonas</i> sp. HXN-200
  作者：Dongliang Chang、Maarten F. Heringa、Bernard Witholt、Zhi Li

  DOI：10.1021/jo034628e

  日期：2003.10.1

  4-dihydroxypiperidines 3 and 3,4-dihydroxypyrrolidines 6, respectively, with high enantioselectivity and high activity. The trans dihydroxylation was sequentially catalyzed by a monooxygenase and an epoxide hydrolase in the strain with epoxide as intermediate. While both epoxidation and hydrolysis steps contributed to the overall enantioselectivity in trans dihydroxylation of 1, the enantioselectivity in trans dihydroxylation

  细菌菌株鞘氨醇单胞菌（Sphingomonas sp。）。HXN-200用于催化N-取代的1,2,5,6-四氢吡啶1和3-吡咯啉4的反二羟基化反应，从而分别以高对映体选择性得到相应的3,4-二羟基哌啶3和3,4-二羟基吡咯烷6。和高活动。在菌株中以环氧化物为中间体，通过单加氧酶和环氧化物水解酶顺序地催化反式二羟基化。尽管环氧化步骤和水解步骤都对1的反式二羟基化反应的总体对映选择性有所贡献，但对称底物4的反式二羟基化反应的对映选择性仅在中环氧化物5的水解中产生。生物产物（+）-3的绝对构型通过化学相关将（+）-6确定为（3R，4R）。用鞘氨醇单胞菌属物种的冷冻/解冻细胞制备1a和4b的反式二羟基化反应。HXN-200在96％ee和60％ee中分别提供了相应的（+）-（3R，4R）-3,4-二羟基哌啶3a和（+）-（3R，4R）-3,4-二羟基吡咯烷6b产率分别为80％。这些结果代表了用非萜底
• ISOQUINUCLIDINE DERIVATIVE AND METHOD FOR MANUFACTURING 1-CYCLOHEXENE-1-CARBOXYLIC ACID DERIVATIVE USING THE SAME
  申请人：Fukuyama Tohru

  公开号：US20100010225A1

  公开（公告）日：2010-01-14

  The present invention provides an isoquinuclidine derivative which can be used to easily synthesize oseltamivir or an analog thereof. In particular, the present invention provides an isoquinuclidine derivative represented by the following formula (1) or an enantiomer thereof: wherein in the formula (1), A represents a protective group for the nitrogen atom; R 1 to R 1 each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent, or a hydrogen atom; and X represents a halogen atom.

  本发明提供了一种异喹啉衍生物，可用于轻松合成奥司他韦或其类似物。特别地，本发明提供了以下公式（1）或其对映体所表示的异喹啉衍生物：其中，在公式（1）中，A代表氮原子的保护基；R1至R4各自独立地表示可以具有取代基的烷基，可以具有取代基的芳基或氢原子；X表示卤素原子。
• Engineered P450pyr monooxygenase for asymmetric epoxidation of alkenes with unique and high enantioselectivity
  作者：Aitao Li、Ji Liu、Son Q. Pham、Zhi Li

  DOI：10.1039/c3cc46675b

  日期：——

  A triple mutant of P450pyr monooxygenase (P450pyrTM) catalysed the epoxidation of several para-substituted styrenes as the first enzyme showing high (R)-enantioselectivity and high conversion, demonstrated a broad substrate range, and showed high enantioselectivity for the epoxidation of an unconjugated 1,1-disubstituted alkene, 2-methyl-3-phenyl-1-propene, and a cyclic alkene, N-phenoxycarbonyl-1,2,5,6-tetrahydropyridine, respectively.

  P450pyr单加氧酶的三重突变体（P450pyrTM）作为首个展现出高（R）对映选择性和高转化率的酶，催化了几种对位取代苯乙烯的环氧化反应，其底物范围广泛，并对非共轭的1,1-二取代烯烃——2-甲基-3-苯基-1-丙烯，以及环烯烃——N-苯氧羰基-1,2,5,6-四氢吡啶的环氧化反应表现出高对映选择性。
• Reactivity of 2-cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic acid esters towards various nucleophiles: Regio- and stereoselectivity of the attack
  作者：P. Stanetty、M. D. Mihovilovic、K. Mereiter

  DOI：10.1007/bf00806971

  日期：1997.10

  The synthesis and reactivity of the title compounds towards nucleophiles are discussed. The regio-and diastereoselectivity of the attack is highly dependent on the carbamic ester and the type of nucleophile applied. Both Michael type addition across the activated double bond and S(N)2T reaction at the carbamate carbon atom were observed. Structure assignment of the adducts in solution and in the solid state was performed utilizing high temperature NMR techniques as well as single crystal X-ray diffraction.