2-bromospiro<5.5>undec-1-ene | 135615-93-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-bromospiro<5.5>undec-1-ene
• 英文别名: 2-bromospiro[5.5]undec-1-ene；4-bromospiro[5.5]undec-4-ene
• CAS: 135615-93-9
• 化学式: C₁₁H₁₇Br
• 分子量: 229.16
• InChiKey: PENTWHWEDBVCSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  Spiro[5.5]undec-1-ene-2-carboxylic acid 4-methyl-2-thioxo-thiazol-3-yl ester 在 偶氮二异丁腈 、 三氯溴甲烷 作用下， 以74%的产率得到2-bromospiro<5.5>undec-1-ene
  参考文献：
  名称：

  Regioselective conversion of cycloalkanones to vinyl bromides with 1,2-functionality transposition. A general stratagem

  摘要：

  Cyclic beta-keto esters, available by regioselective acylation of cycloalkanone enolates, are rapidly transformed to alpha,beta-unsaturated acids. This functionality transposition allows the derived 3-hydroxy-4-methylthiazole-2-(3H)-thione derivatives to serve as precursors to synthetically useful vinyl bromides. The process involves heating the hydroxamate ester with AIBN in bromotrichloromethane solution. Alkylative and ring contractive variants of the methodology are highlighted. The short sequence makes available precursors to vinyl anions that are not otherwise conveniently accessible.

  DOI：

  10.1021/jo00021a044

文献信息

• Synthesis of Spirocyclic Compounds by a Ring-Expansion/Cationic Cyclization Cascade Reaction of Chlorosulfate Derivatives
  作者：Lara Cala、Rubén Rubio-Presa、Olaya García-Pedrero、Francisco J. Fañanás、Félix Rodríguez

  DOI：10.1021/acs.orglett.0c01101

  日期：2020.5.15

  A novel cascade reaction to prepare spirocarbocyclic compounds from chlorosulfate derivatives has been developed. The process involves an unusual thermal elimination of the chlorosulfate moiety, a ring-expansion reaction, and a subsequent cationic cyclization reaction. Despite the relatively complex skeletal rearrangement, the reaction described here is featured by its operational simplicity, being

  已经开发了一种新的级联反应，可以从氯硫酸盐衍生物制备螺碳环化合物。该方法涉及不寻常的热消除氯硫酸盐部分，环扩环反应和随后的阳离子环化反应。尽管骨架重排相对复杂，但此处描述的反应仍具有操作简便的特点，这只是一个不需要额外试剂，催化剂或添加剂的热处理过程。