3,4,4-Trimethyl-2-cyclohexen-1-ol | 73741-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,4-Trimethyl-2-cyclohexen-1-ol
• 英文别名: 3,4,4-Trimethyl-cyclohex-2-en-1-ol；3,4,4-trimethylcyclohex-2-en-1-ol
• CAS: 73741-63-6
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: PFGIRKUZXJBNHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4,4-Trimethyl-2-cyclohexen-1-ol 在 吡啶 、 臭氧 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 2-(acetoxy)-5-methyl-5-[3-methyl-5-phenyl-5-(trifluoromethyl)-1,2,4-trioxolan-3-yl]hexanal
  参考文献：
  名称：

  Ozonolyses of 4,4-Dimethyl-2-cyclohexen-1-yl Acetate and 4,4-Dimethyl-2-cyclopenten-1-yl Acetate. Competition between the Steric Effects of the Allylic Methyl Groups and the Electronic Effects of the Acetoxy Group on the Direction of Cleavage of the Primary Ozonides

  摘要：

  In order to understand the relative directing effects of the substituent steric and electronic effects on the cleavage of the primary ozonides, ozonolyses of a series of cyclohexene and cyclopentene derivatives were conducted in methanol or in ether in the presence of trifluoroacetophenone. The ozonolysis of 4,4-dimethyl-2-cyclohexen-1-yl acetate (1k) in methanol provided exclusively the alpha-methoxyalkyl hydroperoxide 7k derived from capture of 5-acetoxy-5-formyl-2,2-dimethylpentanal oxide by the solvent, while in the case of the relevant 4,4-dimethyl-2-cyclopenten-1-yl acetate (1l) the solvent-captured product 6l derived from trapping of 2-acetoxy-5-formyl-5-methylpentanal oxide was the major product. The remarkable difference in the regiochemistry of the fragmentation between the primary ozonides, 2k and 2l, is rationalized in terms of the significant difference in the steric congestion.

  DOI：

  10.1021/jo960219p

文献信息

• METHODS OF USING NATURAL AND ENGINEERED ORGANISMS TO PRODUCE SMALL MOLECULES FOR INDUSTRIAL APPLICATION
  申请人：Kiverdi, Inc.

  公开号：EP2971023A2

  公开（公告）日：2016-01-20
• US20140273112A1
  申请人：——

  公开号：US20140273112A1

  公开（公告）日：2014-09-18
• Methods of Using Natural and Engineered Organisms to Produce Small Molecules for Industrial Application
  申请人：Kiverdi, Inc.

  公开号：US20170159087A1

  公开（公告）日：2017-06-08

  Aspects of the invention relate to methods of producing small molecules for industrial application using natural organisms and engineered organisms.
• US9556462B2
  申请人：——

  公开号：US9556462B2

  公开（公告）日：2017-01-31
• [EN] METHODS OF USING NATURAL AND ENGINEERED ORGANISMS TO PRODUCE SMALL MOLECULES FOR INDUSTRIAL APPLICATION<br/>[FR] PROCÉDÉS D'UTILISATION D'ORGANISMES NATURELS ET SYNTHÉTIQUES POUR PRODUIRE DE PETITES MOLÉCULES POUR UNE APPLICATION INDUSTRIELLE
  申请人：KIVERDI INC

  公开号：WO2014145194A2

  公开（公告）日：2014-09-18

  Aspects of the invention relate to methods of producing small molecules for industrial application using natural organisms and engineered organisms.