1-(1,4-二甲基环己基)乙酮 | 152468-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(1,4-二甲基环己基)乙酮
• 英文名称: 1-(1,4-dimethyl-cyclohexyl)-ethanone
• 英文别名: 1-(1,4-Dimethyl-cyclohexyl)-aethanon；1-(1,4-Dimethylcyclohexyl)ethanone
• CAS: 152468-75-2
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: WYZQFSCFZQBHMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  1-(1,4-二甲基环己基)乙酮 在 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 三氟甲磺酸 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2RS,3SR)-2-(1,4-Dimethylcyclohexyl)-2-methyl-3-(hydroxymethyl)cyclopentanone
  参考文献：
  名称：

  通过频哪醇类型的环丁烷重排制毒取代环戊酮的便捷途径

  摘要：

  到邻位取代的环戊酮的方便的路线4,8已经经由氧杂二环的重排已开发通过分子内[2 + 2]光环在选自酮衍生得到的二烯类[3.2.0]庚烷1，7。

  DOI：

  10.1016/0040-4039(93)88087-y
• 作为产物：
  描述：

  p-menthane-4,8-diol 在 草酸 作用下， 生成 1-(1,4-二甲基环己基)乙酮
  参考文献：
  名称：

  Monoclonal Autoantibodies from Patients with Autoimmune Diseases: Specificity, Affinity and Crossreactivity of MAbs Binding to Cytoskeletal and Nucleolar Epitopes, Cartilage Antigens and Mycobacterial Heat-Shock Protein 60

  摘要：

  Serum autoantibodies produce typical immunofluorescence staining patterns on HEp-2 cells, which are frequently used for diagnostic purposes. These include antibodies recognizing cytoskeletal and nuclear epitopes. The detailed analysis of human monoclonal antibodies (MAbs) should help to understand which antigens or autoantigens were involved in the generation of these immune responses. Here, three MAbs are described staining HEp-2 cells in a characteristic pattern. They were derived from peripheral blood B cells of two patients with rheumatic diseases (rheumatoid arthritis and relapsing polychondritis). Their binding reactivities were characterized in detail in several assay systems and their affinities measured. Although the antibodies differed in their fine specificity and crossreactivity, all three MAbs (2 IgM, 1 IgA) bound to purified cytoskeletal antigens (desmin) and, in addition, to cartilage antigens (human collagen type 11, proteoglycans). The binding to HEp-2 cells could be inhibited specifically with soluble antigens as shown by intracellular flow cytometry. The affinities for both groups of antigens were relatively high (examples: K-D (desmin) = 0.1 X 10(-7) M; K-D (collagen) = 3.5 X 10(-7) M). Two of the MAbs also bound to heat-shock protein 60 (HSP60) derived from Mycobacterium tuberculosis. The results prove that antibodies and B cells with reactivity to both intracellular cytoskeletal and nuclear antigens and exogenous antigens (e. g. HSP60) exist in patients with rheumatic diseases. Similar to an animal model such human B cells may be induced by the exogenous antigen (IiSP60) and crossreact with local auto-antigens related to the disease (cartilage). In this way they might contribute to pathogenic processes. Due to their additional crossreactivity with intracellular cytoskeletal and nuclear antigens, these antibodies simultaneously can be detected in the HEp-2 immunofluorescence assay.

  DOI：

  10.1078/0171-2985-00107

文献信息

• Regioselectivity and Stereospecificity in a Contrastereoelectronically Controlled Pinacol Rearrangement of Alkoxycyclobutane Derivatives. A Novel Route to Vicinally Substituted Cyclopentanones
  作者：Debasis Patra、Subrata Ghosh

  DOI：10.1021/jo00113a036

  日期：1995.4

  A four-step sequence for the synthesis of vicinally substituted cyclopentanones 5 and 9 has been developed starting from the acyclic ketones 1. The key step involves a stereospecific pinacol-type rearrangement of the cyclobutane ring embodied in oxabicyclo[3.2.0]-heptanes 4 and 8 involving exclusive migration of the stereoelectronically disfavored cyclobutane bond. The oxabicyclo[3.2.0]heptanes have been obtained by copper(I) triflate (CuOTf) catalyzed intramolecular photocycloaddition of the dienes 3 prepared from the ketones 1 on reaction with (ethoxyvinyl)lithium followed by allylation of the carbinols 2. The regioselectivity observed in bond migration has been attributed to be the result of the stabilization of the cation 15 by the neighboring hydroxyl group that is generated during the rearrangement.
• A convenient route to vicinally substituted cyclopentanones via pinacol type rearrangement of cyclobutanes
  作者：Subrata Ghosh、Debasis Patra

  DOI：10.1016/0040-4039(93)88087-y

  日期：1993.7

  A convenient route to the vicinally substituted cyclopentanones 4,8 have been developed via rearrangement of oxabicyclo[3.2.0]heptanes obtained through intramolecular [2+2] photocycloaddition in dienes derived from ketones 1, 7.

  到邻位取代的环戊酮的方便的路线4,8已经经由氧杂二环的重排已开发通过分子内[2 + 2]光环在选自酮衍生得到的二烯类[3.2.0]庚烷1，7。
• Monoclonal Autoantibodies from Patients with Autoimmune Diseases: Specificity, Affinity and Crossreactivity of MAbs Binding to Cytoskeletal and Nucleolar Epitopes, Cartilage Antigens and Mycobacterial Heat-Shock Protein 60
  作者：T MENGE

  DOI：10.1078/0171-2985-00107

  日期：——

  Serum autoantibodies produce typical immunofluorescence staining patterns on HEp-2 cells, which are frequently used for diagnostic purposes. These include antibodies recognizing cytoskeletal and nuclear epitopes. The detailed analysis of human monoclonal antibodies (MAbs) should help to understand which antigens or autoantigens were involved in the generation of these immune responses. Here, three MAbs are described staining HEp-2 cells in a characteristic pattern. They were derived from peripheral blood B cells of two patients with rheumatic diseases (rheumatoid arthritis and relapsing polychondritis). Their binding reactivities were characterized in detail in several assay systems and their affinities measured. Although the antibodies differed in their fine specificity and crossreactivity, all three MAbs (2 IgM, 1 IgA) bound to purified cytoskeletal antigens (desmin) and, in addition, to cartilage antigens (human collagen type 11, proteoglycans). The binding to HEp-2 cells could be inhibited specifically with soluble antigens as shown by intracellular flow cytometry. The affinities for both groups of antigens were relatively high (examples: K-D (desmin) = 0.1 X 10(-7) M; K-D (collagen) = 3.5 X 10(-7) M). Two of the MAbs also bound to heat-shock protein 60 (HSP60) derived from Mycobacterium tuberculosis. The results prove that antibodies and B cells with reactivity to both intracellular cytoskeletal and nuclear antigens and exogenous antigens (e. g. HSP60) exist in patients with rheumatic diseases. Similar to an animal model such human B cells may be induced by the exogenous antigen (IiSP60) and crossreact with local auto-antigens related to the disease (cartilage). In this way they might contribute to pathogenic processes. Due to their additional crossreactivity with intracellular cytoskeletal and nuclear antigens, these antibodies simultaneously can be detected in the HEp-2 immunofluorescence assay.