4-(2'-norbornadienyl)butanal | 166988-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2'-norbornadienyl)butanal
• 英文别名: 4-(2-Bicyclo[2.2.1]hepta-2,5-dienyl)butanal
• CAS: 166988-96-1
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: XCJRGOUESVNCLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  261.1±19.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2'-norbornadienyl)butanal 在 吡啶 、 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 84.0h， 生成 (1S,2R,6R,9R,10R)-7-methyl-8-oxa-7-azatetracyclo[8.2.1.02,6.02,9]tridec-11-ene
  参考文献：
  名称：

  Intramolecular 1,3-Dipolar Cycloadditions of Norbornadiene-Tethered Nitrones

  摘要：

  Efficient routes to the synthesis of norbornadiene-tethered nitrones have been developed, and their intramolecular 1,3-dipolar cycloadditions were studied. The cycloadditions occurred in moderate to good yields for a variety of substrates and were found to be highly regio- and stereoselective, giving single regio- and stereoisomers in most cases.

  DOI：

  10.1021/jo015610b
• 作为产物：
  描述：

  4-(2'-norbornadienyl)butan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到4-(2'-norbornadienyl)butanal
  参考文献：
  名称：

  Intramolecular 1,3-dipolar cycloadditions of 2-substituted norbornadiene-tethered nitrones

  摘要：

  高效率的合成途径已被开发用于制备以降冰片二烯为连接基的硝酮，并发现其分子内的1,3-偶极环加成反应具有高度区域选择性和立体选择性。

  DOI：

  10.1039/b001543l

文献信息

• Intramolecular 1,3-Dipolar Cycloadditions of Norbornadiene-Tethered Nitrile Oxides
  作者：Carol Yip、Sean Handerson、Geoffrey K. Tranmer、William Tam

  DOI：10.1021/jo005611o

  日期：2001.1.1

  Efficient routes to the synthesis of norbornadiene-tethered nitrile oxides have been developed, and their intramolecular 1,3-dipolar cycloadditions were studied. The cycloadditions occurred in good yields for a variety of substrates and were found to be highly regio- and stereoselective, giving single regio- and stereoisomers in most cases.

  已经开发了合成降冰片二烯系氮氧化物的有效途径，并且研究了它们的分子内1，3-偶极环加成反应。对于多种底物，环加成反应的收率很高，并且被发现具有很高的区域和立体选择性，在大多数情况下可得到单一的区域和立体异构体。
• Highly Regio- and Stereoselective Intramolecular 1,3-Dipolar Cycloadditions of Norbornadiene-Tethered Nitrile Oxides
  作者：Carol Yip、Sean Handerson、Robert Jordan、William Tam

  DOI：10.1021/ol990765f

  日期：1999.9.1

  [reaction: see text] Intramolecular cycloadditions with high regio- and stereocontrol are important methods for the efficient assembly of complex molecular structures. Efficient routes to the synthesis of norbornadiene-tethered nitrile oxides have been developed, and their intramolecular 1,3-dipolar cycloadditions were studied. The cycloadditions occurred in good yields for a variety of substrates

  [反应：见正文]具有高度区域控制和立体控制的分子内环加成是有效组装复杂分子结构的重要方法。已经开发了合成降冰片二烯系链的腈氧化物的有效途径，并且研究了它们的分子内1，3-偶极环加成。对于多种底物，环加成反应的收率很高，并且被发现具有很高的区域选择性和立体选择性。
• Lautens, Mark; Tam, William; Lautens, Julia Craig, Journal of the American Chemical Society, 1995, vol. 117, # 26, p. 6863 - 6879
  作者：Lautens, Mark、Tam, William、Lautens, Julia Craig、Edwards, Louise G.、Crudden, Cathleen M.、Smith, A. Catherine

  DOI：——

  日期：——
• Lautens, Mark; Edwards, Louise G.; Tam, William, Journal of the American Chemical Society, 1995, vol. 117, # 41, p. 10276 - 10291
  作者：Lautens, Mark、Edwards, Louise G.、Tam, William、Lough, Alan J.

  DOI：——

  日期：——
• New norbornadiene-tethered fulleropyrrolidines
  作者：Arslan R. Akhmetov、Airat R. Tuktarov、Zarema R. Sadretdinova、Leonard M. Khalilov、Usein M. Dzhemilev

  DOI：10.1016/j.mencom.2020.05.031

  日期：2020.5

  N-Methyl-3,4-fulleropyrrolidine-norbornadiene conjugates with or without (CH2)(n) (n = 0-3) spacers were synthesized by the Prato reaction from the corresponding norbornadiene aldehydes. The influence of the spacer length on the diastereomer composition of the conjugates with two chiral centres studied by C-13 NMR revealed a pronounced diastereotopic splitting of the fullerene carbon signals relating to four diastereomers in the case when the norbornadiene substituent was directly attached to the pyrrolidine moiety. When norbornadiene moiety was separated from the pyrrolidine one by three methylene units, the diastereotopic difference was lower and some of the signals were grouped.