α,α-dibromocyclohexanone | 28867-02-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,α-dibromocyclohexanone
• 英文别名: 2,2-dibromo-cyclohexanone；2,2-Dibrom-cyclohexanon；2,2,-Dibromcyclohexanon；2,2-Dibromcyclohexanon；2,2-Dibromocyclohexan-1-one
• CAS: 28867-02-9
• 化学式: C₆H₈Br₂O
• 分子量: 255.937
• InChiKey: LEONKMRUDSTIPY-UHFFFAOYSA-N

物化性质

• 熔点：
  48-49 °C(Solv: pentane (109-66-0))
• 沸点：
  241.9±40.0 °C(Predicted)
• 密度：
  1.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氧代环己烷羧酸 在 水 、 溴 、 sodium acetate 作用下， 生成 α,α-dibromocyclohexanone
  参考文献：
  名称：

  The Stereochemistry of α-Haloketones. II.¹ The Three α-Dibrominated Cyclohexanones

  摘要：

  DOI：

  10.1021/ja01110a001

文献信息

• In Situ–Generated Zinc Bromide–Catalyzed α‐Bromination of Alkanones in Water
  作者：Satinder K. Juneja、Deepak Choudhary、Satya Paul、Rajive Gupta

  DOI：10.1080/00397910600770714

  日期：2006.9.1

  Abstract α‐Bromination of alkanones with bromine catalyzed by in situ–generated zinc bromide from zinc dust and bromine in water is investigated. Bromination with dioxane‐dibromide as a source of bromine does not require zinc dust and provides selectively α‐mono and α,α‐dibromo products in excellent yields when water is used as solvent.

  摘要 研究了由锌粉原位生成的溴化锌和水中的溴催化烷酮与溴的 α-溴化反应。使用二恶烷-二溴化物作为溴源进行溴化不需要锌粉，并且当使用水作为溶剂时，可以选择性地以优异的收率提供 α-单溴和 α,α-二溴产物。
• Oxybromination catalysed by the heteropolyanion compound H5PMo10V2O40 in an organic medium: selective para-bromination of phenol
  作者：Ronny Neumann、Igal Assael

  DOI：10.1039/c39880001285

  日期：——

  bromination of ketones and alkenes have been achieved by oxybromination at ambient conditions catalysed by the mixed addenda heteropolyanion compound H5PMo10V2O40, which is dissolved in nonpolar chlorohydrocarbon solvent by complexation with tetraglyme.

  苯酚及其衍生物的选择性溴化反应以及酮和烯烃的溴化反应是通过在环境条件下由混合加成杂杂阴离子化合物H 5 PMo 10 V 2 O 40催化氧化溴化而实现的，该杂化阴离子化合物H 5 PMo 10 V 2 O 40通过与四甘醇二甲醚络合而溶解在非极性氯代烃溶剂中。
• Silica gel catalyzed α-bromination of ketones using N-bromosuccinimide: An easy and rapid method
  作者：Bodireddy Mohan Reddy、Velpula Venkata Ramana Kumar、Nallagondu Chinna Gangi Reddy、Siripragada Mahender Rao

  DOI：10.1016/j.cclet.2013.09.014

  日期：2014.1

  An easy and rapid method for the alpha-bromination of ketones using N-bromosuccinimide (NBS) catalyzed by silica gel in methanol under reflux conditions was developed. The expected products were formed in excellent isolated yields within a short period of time (5-20 min). Major advantages of the present procedure include use of inexpensive and readily available catalyst, exclusion of pre- and post-chemical treatment of catalyst and use of methanol as solvent instead of ethers and chlorinated solvents. (C) 2013 Nallagondu Chinna Gangi Reddy. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Rodygin, M. Yu.; Mikhailov, V. A.; Savelova, V. A., Russian Journal of Organic Chemistry, 1994, vol. 30, # 6.1, p. 881 - 887
  作者：Rodygin, M. Yu.、Mikhailov, V. A.、Savelova, V. A.

  DOI：——

  日期：——
• NEUMANN, RONNY;ASSAEL, IGAL, J. CHEM. SOC. CHEM. COMMUN.,(1988) N 19, C. 1285-1287
  作者：NEUMANN, RONNY、ASSAEL, IGAL

  DOI：——

  日期：——