2-(Z)-(bromoiodomethylidene)cyclohexanone | 147727-71-7

• 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-(Z)-(bromoiodomethylidene)cyclohexanone
• 英文别名: 2-<(Z)-bromoiodomethylidene>cyclohexanone；2-[(Z)-bromoiodomethylidene] cyclohexanone；(2Z)-2-[bromo(iodo)methylidene]cyclohexan-1-one
• CAS: 147727-71-7
• 化学式: C₇H₈BrIO
• 分子量: 314.948
• InChiKey: MCOGFXOCYOJSND-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2-(Z)-(bromoiodomethylidene)cyclohexanone 在 双(乙腈)氯化钯(II) 、 三正丁基氢锡 作用下， 生成 2-<(E)-bromomethylidene>cyclohexanone
  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
• 作为产物：
  描述：

  1-(bromoethynyl)cyclopentan-1-ol 在 羟基甲苯磺酰碘苯 碘 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以61%的产率得到2-(Z)-(bromoiodomethylidene)cyclohexanone
  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。
• SYNTHESIS OF HALOENONES AND ARYL OR ALKYL SUBSTITUTED ENONES OR ALKENES
  申请人：NEW YORK UNIVERSITY

  公开号：EP0656878A1

  公开（公告）日：1995-06-14
• EP0656878A4
  申请人：——

  公开号：EP0656878A4

  公开（公告）日：1995-07-05
• US5446203A
  申请人：——

  公开号：US5446203A

  公开（公告）日：1995-08-29
• [EN] SYNTHESIS OF HALOENONES AND ARYL OR ALKYL SUBSTITUTED ENONES OR ALKENES<br/>[FR] SYNTHESE D'HALOENONES ET ENONES OU ALCENES A SUBSTITUTION ARYLE OU ALKYLE
  申请人：NEW YORK UNIVERSITY

  公开号：WO1994005617A1

  公开（公告）日：1994-03-17

  (EN) Alternative methods for synthesizing haloenones and haloalkenes and their use as starting materials for synthesis of substituted or unsubstituted alkyl and aryl substituted enones and alkenes, including tamoxifen and tamoxifen analogs, using such haloenones and haloalkenes.(FR) Procédés de synthèse d'haloénones et d'haloalcènes et utilisation de ces composés comme produits de départ pour la synthèse d'énones et d'alcènes à substitution alkyle et aryle, comprenant le tamoxifène et les analogues de tamoxifène.