1-norborn-2-en-2-yl-propan-1-one | 233769-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-norborn-2-en-2-yl-propan-1-one
• 英文别名: 1-Norborn-2-en-2-yl-propan-1-on；1-(2-Bicyclo[2.2.1]hept-2-enyl)propan-1-one
• CAS: 233769-23-8
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: VIOFUBMBFQFVIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  1-norborn-2-en-2-yl-propan-1-one 、 甲氧苯胺 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 1.0h， 以65%的产率得到
  参考文献：
  名称：

  Synthesis, immunomodulating activity and 1H NMR studies of 7-oxo-9,11-ethano-13-azaprostanoids

  摘要：

  Novel 9,11-ethano analogues of prostaglandin endoperoxides with a nitrogen in position 13 were synthesized. H-1 NMR spectra of the obtained compounds were studied. All prostanoids administered perorally at doses of 2.5-10.0 mug kg(-1) had specific dose-dependent effects on the B-cellular immunity estimated under in vivo conditions on the model of the B-cellular immune response. In terms of the direction of their activities, eight of the studied compounds were found to be immunostimulators, whereas other three compounds displayed immunosuppressing effect. Two of the compounds increased the amount of antibody-forming cells (AFC) per 10(6) spleen cells by 1.9 times in comparison with the respective parameter of control group. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.11.015
• 作为产物：
  描述：

  α-chloronorbornene 在 三氯化铝 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 80.25h， 生成 1-norborn-2-en-2-yl-propan-1-one
  参考文献：
  名称：

  2-三甲基甲硅烷基降冰片烯的Friedel-Crafts酰化。酰基对攻击位置的影响

  摘要：

  2-三甲基甲硅烷基降冰片烯1在氯化铝存在下的酰化作用可得到少量的预期2-降冰片烯基酮4。作为主要产物的3和5的形成表明，主要取决于酰基的性质而发生α攻击或β攻击，而β硅效应不是决定性因素。β-甲硅烷基阳离子中间体2主要通过1，3-去质子化产生正三环基酮3，并且α-甲硅烷基阳离子8经历重排以产生新颖的桥头甲硅烷基化产物5。

  DOI：

  10.1016/s0040-4020(99)00402-0

文献信息

• Oxidative decyanation of secondary nitriles to ketones
  作者：Robert W. Freerksen、Sandra J. Selikson、Randall R. Wroble、Keith S. Kyler、David S. Watt

  DOI：10.1021/jo00170a043

  日期：1983.11
• Kotschetkow; Chorlin, Zhurnal Obshchei Khimii, 1957, vol. 27, p. 3182,3186; engl. Ausg. S. 3217, 3220
  作者：Kotschetkow、Chorlin

  DOI：——

  日期：——
• FREERKSEN, R. W.;SELIKSON, S. J.;WROBLE, R. R.;KYLER, K. S.;WATT, D. S., J. ORG. CHEM., 1983, 48, N 22, 4087-4096
  作者：FREERKSEN, R. W.、SELIKSON, S. J.、WROBLE, R. R.、KYLER, K. S.、WATT, D. S.

  DOI：——

  日期：——
• Friedel-Crafts acylation of 2-trimethylsilylnorbornene. Effect of acyl group on the position of attack
  作者：Gopalpur Nagendrappa、Noor Shahina Begum

  DOI：10.1016/s0040-4020(99)00402-0

  日期：1999.6

  The acylation of 2-trimethylsilylnorbornene 1 in the presence of aluminium chloride gives minor quantities of the expected 2-norbornenyl ketones 4. The formation of 3 and 5 as major products indicates that either α-or β-attack takes place predominantly depending on the nature of the acyl group, and the β-silicon effect is not a decisive factor. The β-silyl cation intermediate 2 mainly leads to nortricyclyl

  2-三甲基甲硅烷基降冰片烯1在氯化铝存在下的酰化作用可得到少量的预期2-降冰片烯基酮4。作为主要产物的3和5的形成表明，主要取决于酰基的性质而发生α攻击或β攻击，而β硅效应不是决定性因素。β-甲硅烷基阳离子中间体2主要通过1，3-去质子化产生正三环基酮3，并且α-甲硅烷基阳离子8经历重排以产生新颖的桥头甲硅烷基化产物5。
• Synthesis, immunomodulating activity and 1H NMR studies of 7-oxo-9,11-ethano-13-azaprostanoids
  作者：Natalia F. Bondar、Marina B. Golubeva、Lyudmila P. Isaenya、Nicolay A. Konoplya、Boleslav B. Kuzmitsky、Gennadi S. Lyubin

  DOI：10.1016/j.ejmech.2003.11.015

  日期：2004.5

  Novel 9,11-ethano analogues of prostaglandin endoperoxides with a nitrogen in position 13 were synthesized. H-1 NMR spectra of the obtained compounds were studied. All prostanoids administered perorally at doses of 2.5-10.0 mug kg(-1) had specific dose-dependent effects on the B-cellular immunity estimated under in vivo conditions on the model of the B-cellular immune response. In terms of the direction of their activities, eight of the studied compounds were found to be immunostimulators, whereas other three compounds displayed immunosuppressing effect. Two of the compounds increased the amount of antibody-forming cells (AFC) per 10(6) spleen cells by 1.9 times in comparison with the respective parameter of control group. (C) 2004 Elsevier SAS. All rights reserved.