(1R,8S,9S,13R)-11-methyl-14-oxa-11-azatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6-triene-10,12-dione | 32427-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (1R,8S,9S,13R)-11-methyl-14-oxa-11-azatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6-triene-10,12-dione
• CAS: 32427-43-3
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: LMUSZMPVOYVNRL-CKIJPRSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,4-dihydro-1,4-epoxy-3-phenylisoquinoline 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (1R,8S,9S,13R)-11-methyl-14-oxa-11-azatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6-triene-10,12-dione
  参考文献：
  名称：

  Benzyne-oxazole cycloadducts: isolation and retro-Diels-Alder reactions

  摘要：

  DOI：

  10.1021/jo00290a025

文献信息

• Approaches to Open Fullerenes:  Synthesis and Kinetic Stability of Diels−Alder Adducts of Substituted Isobenzofurans and C₆₀
  作者：Shih-Ching Chuang、Michael Sander、Thibaut Jarrosson、Scott James、Eugene Rozumov、Saeed I. Khan、Yves Rubin

  DOI：10.1021/jo061986j

  日期：2007.4.1

  examined the reactions of 1,3-disubstituted isobenzofurans with the fullerene C60 in the context of an approach to open a large orifice on the fullerene framework. A variety of substituted isobenzofurans (6a−h), generated from the reaction of 1,4-substituted 1,4-epoxynaphthalenes 3a−h with 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine (4a) or 1,2,4,5-tetrazine (4b), were added to C60 to afford the Diels−Alder adducts

  我们已经研究了在富勒烯骨架上开大孔的方法中1，3-二取代异苯并呋喃与富勒烯C 60的反应。1,4-取代的1,4-环氧萘3a - h与3,6-双（2-吡啶基）-1,2,4,5-四嗪反应生成的各种取代的异苯并呋喃（6a - h）将（4a）或1,2,4,5-四嗪（4b）添加到C 60中以提供Diels-Alder加合物7a - h。这些加合物对逆Diels-Alder碎裂的热稳定性在溶液中与固态有很大不同。在溶液中，单加成物的相对容易的逆狄尔斯-阿尔德碎裂7A和图7C，得到C，60和自由isobenzofurans 6A和6C，具有速率常数（和活化障碍）ķ = 9.29×10 - 5个小号- 1在70℃（Ë一个= 32.6千卡摩尔- 1）和ķ = 1.36×10 - 4个小号- 1在40℃下（Ëa = 33.7 kcal mol - 1），表明在这些温度下向C 60中添加异苯并呋喃很容易可逆。在
• Rigid Alicyclic Molecules from Bicyclo[2.2.1]hept-2-enes (=8,9,10-Trinorbornenes) and 1,4-Dipyridin-2-ylphthalazines as Stereoselective Coupling Agents
  作者：Davor Margetić、Yasujiro Murata、Koichi Komatsu、Željko Marinić

  DOI：10.1002/hlca.200800205

  日期：2009.2

  Abstractmagnified imageFor the preparation of rigid polycyclic molecules from 8,9,10‐trinorbornenes (=bicyclo[2.2.1]hept‐2‐enes), 1,4‐dipyridin‐2‐ylphthalazines were used. Cycloaddition reactions with trinorbornenes gave coupled products in a stereoselective manner. In these reactions, the phthalazines delivered a new bicyclo[2.2.2] moiety at the junction of two trinorbornene units, which could bear appropriate functional groups (Schemes 4and5). The crystal structure of a key cycloadduct,i.e., of18was also determined (Fig. 2). Relative reactivities for a series of phthalazines (Fig. 3) were estimated by density‐functional‐theory (DFT) calculations at the B3LYP/6‐31G* level (Table). The calculations indicated an increase of reactivity when the aromaticity of the phthalazine moiety is decreased. Finally, experimentally observed stereoselectivities of the phthalazine reactions with trinorbornenes were readily predicted by DFT calculations (Fig. 4).
• WHITNEY, S. E.;RICKBORN, B., J. ORG. CHEM., 53,(1988) N 23, C. 5595-5596
  作者：WHITNEY, S. E.、RICKBORN, B.

  DOI：——

  日期：——