(Z)-2-(bromoiodomethylidene)-6-methylcyclohexanone | 147727-79-5

• 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: (Z)-2-(bromoiodomethylidene)-6-methylcyclohexanone
• 英文别名: 2-<(Z)-bromoiodomethylidene>-6-methylcyclohexanone；(2Z)-2-[bromo(iodo)methylidene]-6-methylcyclohexan-1-one
• CAS: 147727-79-5
• 化学式: C₈H₁₀BrIO
• 分子量: 328.975
• InChiKey: ORQVVWXXFHRPIH-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  (Z)-2-(bromoiodomethylidene)-6-methylcyclohexanone 在 氘代甲醇-d 、 乙酸-D3 、 sodium methylate 作用下， 生成 (Z)-2-(bromoiodomethylidene)-6-methylcyclohexanone-6-d
  参考文献：
  名称：

  1-卤乙炔基-2-甲基环戊醇的扩环

  摘要：

  用碘和HTIB环处理的1-卤代乙炔基-2-甲基环戊醇根据甲基和羟基的相对位置而立体选择性地膨胀。该产品是2-（二卤代）-3- methylcyclohexanones如果甲基的是顺式的羟基基团或2-（二卤代）-6- methylcyclohexanones如果甲基的是反式的羟基。

  DOI：

  10.1016/0040-4020(96)00561-3
• 作为产物：
  描述：

  1-(bromoethynyl)cyclopentan-1-ol 在 羟基甲苯磺酰碘苯 碘 、 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 (Z)-2-(bromoiodomethylidene)-6-methylcyclohexanone
  参考文献：
  名称：

  Ring expansions of alkynyl cyclopentanols with iodine and Koser's reagent.

  摘要：

  Equimolar amounts of iodine, Koser's reagent, and 1-bromoethynylcyclopentanols with none, one or two methyl groups in the alpha-position lead to ring expansions in acetonitrile at room temperature in yields of 75 to 85%. In the so-formed 2-[bromoiodomethylidene]cyclohexanones the (Z) isomer was preferred exclusively in the unsubstituted compound. The Z/E ratio was 7.7 for the dimethyl compound and 3.3 for the monomethyl case. The corresponding bromine and Koser's reagent with 1-iodoethynylcyclopentanol afforded a ring expanded product with Z/E ratio of 12:1.

  DOI：

  10.1016/s0040-4020(01)80339-2

文献信息

• Ring expansions of 1-Haloethynyl-2-methylcyclopentanols
  作者：Xavier Herault、Edward Mc Nelis

  DOI：10.1016/0040-4020(96)00561-3

  日期：1996.7

  1-Haloethynyl-2-methylcyclopentanols treated with iodine and HTIB ring expand stereoselectively depending on the relative position of the methyl and the hydroxyl groups. The products are 2-(dihalomethylidene)-3-methylcyclohexanones if the methyls are cis to the hydroxyl groups or 2-(dihalomethylidene)-6-methylcyclohexanones if the methyls are trans to the hydroxyls.

  用碘和HTIB环处理的1-卤代乙炔基-2-甲基环戊醇根据甲基和羟基的相对位置而立体选择性地膨胀。该产品是2-（二卤代）-3- methylcyclohexanones如果甲基的是顺式的羟基基团或2-（二卤代）-6- methylcyclohexanones如果甲基的是反式的羟基。
• Ring expansions of alkynyl cyclopentanols with iodine and Koser's reagent.
  作者：Pakorn Bovonsombat、Edward McNelis

  DOI：10.1016/s0040-4020(01)80339-2

  日期：——

  Equimolar amounts of iodine, Koser's reagent, and 1-bromoethynylcyclopentanols with none, one or two methyl groups in the alpha-position lead to ring expansions in acetonitrile at room temperature in yields of 75 to 85%. In the so-formed 2-[bromoiodomethylidene]cyclohexanones the (Z) isomer was preferred exclusively in the unsubstituted compound. The Z/E ratio was 7.7 for the dimethyl compound and 3.3 for the monomethyl case. The corresponding bromine and Koser's reagent with 1-iodoethynylcyclopentanol afforded a ring expanded product with Z/E ratio of 12:1.