endo-6'-Carbomethoxyspiro<1,3-dioxolane-2,2'-bicyclo<2.2.1>heptane> | 70600-43-0

• 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: endo-6'-Carbomethoxyspiro<1,3-dioxolane-2,2'-bicyclo<2.2.1>heptane>
• 英文别名: endo-2-carbomethoxyspiro[1,3-dioxolane-2,2'-bicyclo[2.2.1]heptane]；methyl 6-oxonorbornane-2-endo-carboxylate 6-ethylene ketal；methyl (1'R,2'S,4'S)-spiro[1,3-dioxolane-2,6'-bicyclo[2.2.1]heptane]-2'-carboxylate
• CAS: 70600-43-0
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: YQIWDRUGUWMLNU-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  endo-6'-Carbomethoxyspiro<1,3-dioxolane-2,2'-bicyclo<2.2.1>heptane> 在 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 endo-6-formylspiro[1,3-dioxolane-2,2'-bicyclo[2.2.1]heptane]
  参考文献：
  名称：

  Monoamine oxidase-catalyzed oxidation of endo,endo -2-amino-6-[( Z )-2′-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate

  摘要：

  An 11-step synthesis of endo,endo-2-amino-6-[(E)-2'-phenyl]ethenylbicyclo[2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00094-8
• 作为产物：
  描述：

  (+/-)-6-oxobicyclo<2.2.1>heptane-endo-2-carboxylic acid 在 对甲苯磺酸 作用下， 以 甲醇 、 苯 为溶剂， 反应 8.0h， 生成 endo-6'-Carbomethoxyspiro<1,3-dioxolane-2,2'-bicyclo<2.2.1>heptane>
  参考文献：
  名称：

  Monoamine oxidase-catalyzed oxidation of endo,endo -2-amino-6-[( Z )-2′-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate

  摘要：

  An 11-step synthesis of endo,endo-2-amino-6-[(E)-2'-phenyl]ethenylbicyclo[2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00094-8

文献信息

• Photochemistry of alkyl halides. 8. Formation of a bridgehead alkene
  作者：Paul J. Kropp、Paul R. Worsham、Robert I. Davidson、Tappey H. Jones

  DOI：10.1021/ja00378a033

  日期：1982.7
• Chemical Consequences of Long-Range Orbital Interactions in Norbornane-Based 1,4-Diol Monosulfonate Esters
  作者：Petrus M. F. M. Bastiaansen、Joannes B. P. A. Wijnberg、Aede de Groot

  DOI：10.1021/jo00118a046

  日期：1995.6

  Seven monotosylated 1,4-diols with the rigid norbornane skeleton were treated with a strong base in refluxing benzene to find out whether these compounds react by initial heterolysis of the tosylate ester bond induced by long-range orbital interactions. The tosylates 1-7 were designed to investigate the influence of the sigma-relay (U-, sickle-, or W-shaped) between the donor and acceptor end of the system, to check whether primary carbocationic ion pairs could act as intermediates, and to study conformational influences on reactivity and product formation. Tosylate 1 with a U-like arrangement of the sigma-relay reacted relatively slowly and followed reaction pathways in which no long-range orbital interactions are involved. The reaction outcome of tosylate 2 which possesses a sickle-like arrangement of the sigma-relay indicates two competitive processes with and without the involvement of long-range orbital interactions. The secondary tosylates 3, 6, and 7 which all possess a W-like arrangement reacted relatively fast and showed predominantly homofragmentation. Although an ideal W-like arrangement is present in the primary tosylates 4 and 5, no reactions in which long-range orbital interactions are involved were observed. The tosylates 6 and 7 in which the tosylate group is conformationally mobile can give rise to mixtures of products. The ratio in which these products are formed can be rationalized by using the Curtin-Hammett principle.
• Monoamine oxidase-catalyzed oxidation of endo,endo -2-amino-6-[( Z )-2′-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate
  作者：Xueqing Wang、Richard B Silverman

  DOI：10.1016/s0968-0896(00)00094-8

  日期：2000.7

  An 11-step synthesis of endo,endo-2-amino-6-[(E)-2'-phenyl]ethenylbicyclo[2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.