3-chlorobicyclobutanecarbonitrile | 23745-75-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-chlorobicyclobutanecarbonitrile
• 英文别名: 3-Chlorobicyclo[1.1.0]butane-1-carbonitrile
• CAS: 23745-75-7
• 化学式: C₅H₄ClN
• 分子量: 113.546
• InChiKey: OVSLTIVJEFPORJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  3-chlorobicyclobutanecarbonitrile 在 potassium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 504.0h， 以60%的产率得到3-bromobicyclobutanecarbonitrile
  参考文献：
  名称：

  Cyclobutane-bicyclobutane systems. 5. Zwitterionic bicyclobutane: an intermediate in the course of nucleophilic vinylic-like substitution reaction on 3-halobicyclobutanecarbonitrile

  摘要：

  DOI：

  10.1021/ja00364a038
• 作为产物：
  描述：

  3,3-dichlorocyclobutanecarbonitrile 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 3-chlorobicyclobutanecarbonitrile
  参考文献：
  名称：

  Conversion of cyclobutane to bicyclobutane by base-catalyzed 1,3-dehydrohalogenation reaction: a mechanistic study

  摘要：

  DOI：

  10.1021/ja00258a038

文献信息

• An unusual case of proton removal from an oxacarbenium ion
  作者：Shmaryahu Hoz、Doron Aurbach

  DOI：10.1039/c39840000364

  日期：——

  Proton loss from an oxocarbenium moiety of ionic bicyclobutane is found to compete appreciably with the capture of the oxocarbenium by alcohol molecules.

  发现离子双环丁烷的氧碳鎓部分的质子损失与醇分子捕获氧碳鎓明显竞争。
• Bridgehead substituents effect on the reactivity of bicyclobutane in its reactions with nucleophiles. A comparison with olefinic systems
  作者：Carmela Azran、Shmaryahu Hoz

  DOI：10.1016/0040-4020(95)00706-e

  日期：1995.10

  The reactivity of bridgehead substituted bicyclobutanes towards nucleophilic attack was compared with that of the analogous vinylic compounds. Ab initio calculations suggest that the substituents exert nearly the same energetic effects on the ground state of the two systems. The observed difference in the reactivity of the two systems stems, therefore, from the different nature of corresponding transition

  将桥头取代的双环丁烷对亲核攻击的反应性与类似乙烯基化合物的反应性进行了比较。从头算计算表明，取代基对两个系统的基态几乎具有相同的能量效应。因此，观察到的两个系统反应性的差异源于相应过渡态的不同性质。
• Formation and stability of alkoxyimidates in the cyclobutane bicyclobutane system
  作者：S. Hoz、D. Aurbach

  DOI：10.1016/s0040-4020(01)96532-9

  日期：1985.1

  The reactions of CN- with methyl-3-chlorobicyclobutanecarboxylate and 3-chloro and 3-bromobicyclobutanecarbonitrile in MeOH were investigated. The MeO- present in the reaction mixture adds reversibly to the carbonitrile function of the various products. The equilibrium constants for the imidate formation were determined. The general notion that the imidate form is favored by an electron withdrawing

  CN的反应-用甲基-3- chlorobicyclobutanecarboxylate和3-氯和在MeOH 3- bromobicyclobutanecarbonitrile进行了研究。所述的MeO -存在于反应混合物中可逆地增加了各种产品的腈功能。确定亚氨酸酯形成的平衡常数。再次确认了亚氨酸酯形式受到吸电子基团的普遍支持。发现的顺序为CN> Cl≈Br> C（NH）OMe> CO 2 Me。还发现双环丁烷的中心键是电子效应的透射的良好介体。所述alkoxyimidates的独特的稳定性相比，用CN相应加合物的低稳定性-进行了讨论。
• Tuning carbanion reactivity by complexing with boranes: γ‐elimination reaction as a model
  作者：Uri Habusha、Esther Rozental、Shmaryahu Hoz

  DOI：10.1002/poc.814

  日期：2004.11

  γ-elimination reactions [Eqn (1)]. With highly acidic alcohols such as trifluoroethanol the protonation is diffusion controlled and the rate for the cross ring elimination reaction is greater by a factor of three (at an alcohol concentration of 1 M). However, in the presence of BH3 or Bu3B, the protonated product becomes dominant. This result is attributed to the binding of the carbanion by the boranes. Experimental

  3-氯-3-苯基硒代环丁烷甲腈的阴离子在乙醇中，竞争性质子化和γ消除反应中在DME中经历[等式（1）]。对于高酸性醇，例如三氟乙醇，质子化是受扩散控制的，并且消除环环的反应速率提高了三倍（在醇浓度为1  M时）。但是，在BH 3或Bu 3 B的存在下，质子化产物占主导地位。该结果归因于硼烷对碳负离子的结合。实验数据以及从头算计算表明，优选的络合位点是环碳而不是络合物的氰基氮。结果还表明，复杂的直接质子化不是可行的发现合理化。提出增强的质子化是由于在醇和氰基氮之间形成氢键，从而增加了质子给体的有效摩尔浓度，该质子给体在C-B键解离时迁移至α-碳。版权所有©2004 John Wiley＆Sons，Ltd.
• Cyclobutane-bicyclobutane system. 2. Ionic bicyclobutane as an intermediate in the reaction of PhS- with 3-halobicyclobutanecarbonitrile: comparison between thio- and oxycarbenium ions
  作者：Shmaryahu Hoz、Doron Aurbach

  DOI：10.1021/jo00192a008

  日期：1984.9