anti-7-tert-butoxybicyclo[2.2.1]hept-2-ene | 3391-05-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: anti-7-tert-butoxybicyclo[2.2.1]hept-2-ene
• 英文别名: anti-7-tert.-Butyloxy-norbornen；7anti-tert-Butyloxy-norbornen-(2)；anti-7-t-Butoxynorbornen
• CAS: 3391-05-7
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: UMDQECVVQDRXIA-MYJAWHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  anti-7-tert-butoxybicyclo[2.2.1]hept-2-ene 以80%的产率得到
  参考文献：
  名称：

  WILT, J. W.;CURTIS, V. A.;CONGSON, L. N.;PALMER, R., J. ORG. CHEM., 1984, 49, N 16, 2937-2942

  摘要：

  DOI：
• 作为产物：
  描述：

  降冰片烯 在 吡啶 、 一氯化碘 作用下， 生成 anti-7-tert-butoxybicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Addition of ICl to Norbornene. The Preparation and Photochemical Isomerization of syn-7-Iodonorbornene

  摘要：

  在吡啶存在下，将 ICl 加到去氢莰烯会生成主要产物：去氢三环碘化物 (1c)、内-2-氯-外-3-碘去氢莰烷 (2c) 和 同向-7-碘-外-2-氯去氢莰烷 (3b)。对 3b 进行碱催化的 HCl 消除会生成同向-7-碘去氢莰烯 (6a)，该化合物经光化学异构化反应得到反向-7-碘去氢莰烯 (6b)。

  DOI：

  10.1139/v72-042

文献信息

• Ruthenium(II)-Catalyzed [2+2] Cycloadditions ofanti 7-Substituted Norbornenes
  作者：Robert W. Jordan、Paul Le Marquand、William Tam

  DOI：10.1002/ejoc.200700706

  日期：2008.1

  The ruthenium(II)-catalyzed [2+2] cycloadditions of anti 7-substituted norbornenes with an alkyne were investigated. The cycloadditions were found to proceed with a high degree of stereoselectivity, giving only the exo stereoisomers in moderate to good yields using an improved protocol. Comparative rate studies between a variety of anti 7-substituted norbornenes and an alkyne revealed that the reactivity

  研究了钌 (II) 催化的反 7-取代降冰片烯与炔烃的 [2+2] 环加成反应。发现环加成以高度的立体选择性进行，使用改进的方案仅以中等至良好的产率给出外立体异构体。各种反 7-取代降冰片烯和炔烃之间的速率比较研究表明，随着烯烃变得更加缺电子，烯烃组分的反应性急剧下降。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国， 2008)
• Butler,D.N., Synthetic Communications, 1977, vol. 7, p. 441 - 448
  作者：Butler,D.N.

  DOI：——

  日期：——
• Stereoselectivity in the Rhodium-Catalysed Reductions of Non-Conjugated Dienes
  作者：Bao Nguyen、John M. Brown

  DOI：10.1002/adsc.200900013

  日期：2009.6

  Abstractmagnified imageThe stereochemical course of rhodium‐catalysed addition of hydrogen and catecholborane to bicyclo[2.2.1]heptadiene, and of hydrogen to a range of cyclic dienes has been analysed. For hydroboration, the overall catalytic reaction possesses exo‐selectivity, but the initial step is endo‐selective. For hydrogenation (deuteration), the first step may occur with either exo‐ or endo‐ selectivity, depending on the structure of the diene. This enables a distinction to be made between pathways involving prior dissociation of the diene, and direct addition to the complexed diene without full dissociation. The relative ease of hydrogenation of the first and second double bonds varies markedly with reactant structure, and also depends on the choice of catalyst ligands. For dicyclopentadiene, hydrogenation of the cyclopentene double bond is accompanied by rapid alkene isomerisation, as revealed by deuterium addition. The asymmetric hydrogenation of acyclic skipped meso‐dienes is reported, demonstrating control of relative rates of the two sequential steps, with ees of up to 53% after the first reduction.
• GASSMAN, P. G.;HALL, J. B., J. AMER. CHEM. SOC., 1984, 106, N 15, 4267-4269
  作者：GASSMAN, P. G.、HALL, J. B.

  DOI：——

  日期：——
• Klumpp,G.W. et al., Justus Liebigs Annalen der Chemie, 1967, vol. 706, p. 47 - 67
  作者：Klumpp,G.W. et al.

  DOI：——

  日期：——