exo-2-(methoxycarbonyl)norbornane | 16646-41-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: exo-2-(methoxycarbonyl)norbornane
• 英文别名: (1R)-norbornane-2exo-carboxylic acid methyl ester；(1R)-Norbornan-2exo-carbonsaeure-methylester；2-exo-Carbomethoxy-norbornan；N-(1-Ethyl-4-[(2-oxo-1,2-dihydro[1,5]naphthyridin-4-yl)amino]butyl)acetamide；methyl (1R,2R,4S)-bicyclo[2.2.1]heptane-2-carboxylate
• CAS: 16646-41-6；23057-38-7；35520-81-1；61967-04-2；78392-10-6
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: BWGIKEUGPCOETD-XLPZGREQSA-N

物化性质

• 沸点：
  42 °C(Press: 1.7 Torr)
• 密度：
  1.0393 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (1'S,2'R,4'R)-spiro[1,3-dithiolane-2,3'-bicyclo[2.2.1]hept-5-ene]-2'-carboxylate 生成 exo-2-(methoxycarbonyl)norbornane
  参考文献：
  名称：

  CHAMBERLAIN P.; ROONEY A., TETRAHEDRON LETT., 1979, NO 4, 383-386

  摘要：

  DOI：

文献信息

• [EN] INDOLES FOR USE IN INFLUENZA VIRUS INFECTION<br/>[FR] INDOLES POUVANT ÊTRE UTILISÉS DANS L'INFECTION PAR LE VIRUS INFLUENZA
  申请人：JANSSEN SCIENCES IRELAND UC

  公开号：WO2016020526A1

  公开（公告）日：2016-02-11

  The invention relates to compounds having the structure of formula (I) which can be used for the treatment of or against influenza infections.

  这项发明涉及具有式（I）结构的化合物，可用于治疗或预防流感感染。
• Room temperature asymmetric Pd-catalyzed methoxycarbonylation of norbornene: highly selective catalysis and HP-NMR studies
  作者：Carolina Blanco、Cyril Godard、Ennio Zangrando、Aurora Ruiz、Carmen Claver

  DOI：10.1039/c2dt30267e

  日期：——

  Palladium complexes bearing monodentate and bidentate phosphine ligands (1–7) were synthesised and used as catalyst precursors in the methoxycarbonylation of norbornene. The catalytic systems bearing ligands 1, 3 and 4 afforded excellent conversions (>99%) and selectivity of the ester (>99%). NMR investigations showed that using complex 1a as the precursor resulted in the protonated phosphine, 1-H+, being formed under catalytic conditions and thus the addition of acid is not required for the activation of this system since the reaction involving the precursor with methanol under CO pressure produces 2 equivalents of HCl and leads to the formation of the active species. The protonation of ligand 4 under methoxycarbonylation conditions was also observed and the diprotonated diphosphine was isolated and characterised. This compound was tested as a ligand and acid source in a catalysis and provided excellent conversion and high selectivity to the ester.

  合成了带有单齿和双齿膦配体（1-7）的钯配合物，并将其用作降冰片烯甲氧基羰基化反应的催化剂前体。含有配体 1、3 和 4 的催化体系具有优异的酯转化率（大于 99%）和选择性（大于 99%）。核磁共振研究表明，使用配合物 1a 作为前体，在催化条件下会形成质子化的膦 1-H+，因此该体系的活化不需要添加酸，因为在 CO 压力下，前体与甲醇反应会产生 2 个当量的 HCl，从而形成活性物质。此外，还观察到配体 4 在甲氧基羰基化条件下发生质子化，并分离和鉴定了二质子化的二膦。该化合物作为配体和酸源在催化反应中进行了测试，并提供了极佳的酯转化率和高选择性。
• Unprecedent Chemo- and Stereoselective Palladium-Catalysed Methoxycarbonylation of Norbornene
  作者：Carolina Blanco、Aurora Ruiz、Cyril Godard、Nicolas Fleury-Brégeot、Angela Marinetti、Carmen Claver

  DOI：10.1002/adsc.200900025

  日期：——

  Catalytic systems able to control chemo- and stereoselectivity have been tested in the palladium-catalysed methoxycarbonylation of norbornene. An enantioselectivity of up to 40% was obtained.

  在钯催化的降冰片烯的甲氧基羰基化反应中已经测试了能够控制化学和立体选择性的催化体系。获得高达40％的对映选择性。
• Stapersma, J.; Kuipers, P.; Klumpp, G. W., Recueil des Travaux Chimiques des Pays-Bas, 1982, vol. 101, # 6, p. 213 - 218
  作者：Stapersma, J.、Kuipers, P.、Klumpp, G. W.

  DOI：——

  日期：——
• Resolution, Stereochemial Correlation and Maximum Rotations of the Norbornane- and 5-Norbornene-2-carboxylic Acids. Isotope Dilution as an Aid in the Determination of Optical Purity¹
  作者：Jerome A. Berson、David A. Ben-Efraim

  DOI：10.1021/ja01524a066

  日期：1959.8