1-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)ethanone | 1184959-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)ethanone
• 英文别名: 1-(1,1,3,3-tetramethyl-2H-1,3-benzodisilol-5-yl)ethanone
• CAS: 1184959-51-0
• 化学式: C₁₃H₂₀OSi₂
• 分子量: 248.472
• InChiKey: DYPZSFNWSXMJPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (S)-(+)-1,2-丙二醇 、 1-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)ethanone 在 对甲苯磺酸 作用下， 以 水 、 甲苯 为溶剂， 反应 4.0h， 以26%的产率得到(2R,4S)-2,4-dimethyl-2-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)-1,3-dioxolane
  参考文献：
  名称：

  Okoumal和Disila-Okoumal的较低同源物：新型龙涎香气味的合成和嗅觉表征

  摘要：

  一种结构，气味的关系上的低级同系物研究中的龙涎香气味物质okoumal与E1  CH 2  EL（3：埃尔= C; 4：埃尔= Si）或埃尔 ö 埃尔部分（5：埃尔= SI）为执行。合成了3 – 5的所有四种立体异构体，并通过气味描述和检测阈值进行了表征。测量了2 R配置的异构体的最低气味阈值，其中2 R，4 R配置为4 a（El = Si，X = CH 2）是该系列中最浓烈的，并且就其气味而言也是最好的。

  DOI：

  10.1002/cbic.200900680
• 作为产物：
  描述：

  乙炔基-[[乙炔基(二甲基)甲硅烷基]甲基]-二甲基硅烷 在 manganese(IV) oxide 、 carbon monoxide,cobalt,cyclopenta-1,3-diene 、 溶剂黄146 作用下， 以 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 1-(1,1,3,3-tetramethyl-1,3-disilaindan-5-yl)ethanone
  参考文献：
  名称：

  Development of novel silicon-containing inverse agonists of retinoic acid receptor-related orphan receptors

  摘要：

  Retinoic acid receptor (RAR)-related orphan receptors (RORs) regulate a variety of physiological processes, including hepatic gluconeogenesis, lipid metabolism, circadian rhythm and immune function. The RAR agonist: all-trans retinoic acid was reported to be an ROR beta inverse agonist, but no information is available regarding ROR activity of its synthetic analogue Am580. Therefore, we screened Am580 and some related tetramethyltetrahydronaphthalene derivatives and carried out structural development studies, including substitution of carbon atoms with silicon, with the aim of creating a potent ROR transcriptional inhibitor. The phenyl amide disila compound 22 showed the most potent ROR-inhibitory activity among the compounds examined. Its activity towards ROR alpha, ROR beta and ROR gamma was increased compared to that of Am580. The IC50 values for ROR alpha, ROR beta and ROR gamma are 1.3, > 10 and 4.5 mu M, respectively. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.023

文献信息

• Development of novel silicon-containing inverse agonists of retinoic acid receptor-related orphan receptors
  作者：Hirozumi Toyama、Masaharu Nakamura、Masahiko Nakamura、Yotaro Matsumoto、Madoka Nakagomi、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2014.01.023

  日期：2014.3

  Retinoic acid receptor (RAR)-related orphan receptors (RORs) regulate a variety of physiological processes, including hepatic gluconeogenesis, lipid metabolism, circadian rhythm and immune function. The RAR agonist: all-trans retinoic acid was reported to be an ROR beta inverse agonist, but no information is available regarding ROR activity of its synthetic analogue Am580. Therefore, we screened Am580 and some related tetramethyltetrahydronaphthalene derivatives and carried out structural development studies, including substitution of carbon atoms with silicon, with the aim of creating a potent ROR transcriptional inhibitor. The phenyl amide disila compound 22 showed the most potent ROR-inhibitory activity among the compounds examined. Its activity towards ROR alpha, ROR beta and ROR gamma was increased compared to that of Am580. The IC50 values for ROR alpha, ROR beta and ROR gamma are 1.3, > 10 and 4.5 mu M, respectively. (C) 2014 Elsevier Ltd. All rights reserved.
• Lower Homologues of Okoumal and Disila-Okoumal: Synthesis and Olfactory Characterization of Novel Ambergris Odorants
  作者：Jennifer B. Nätscher、Nadine Laskowski、Philip Kraft、Reinhold Tacke

  DOI：10.1002/cbic.200900680

  日期：2010.2.15

  ElOEl moiety (5: El=Si) was carried out. All four stereoisomers of 3–5 were synthesized and characterized by odor descriptions and detection thresholds. The lowest odor thresholds were measured for the 2R configured isomers, with the 2R,4R configured 4 a (El=Si, X=CH2) being the most intense of the series and best also with respect to its odor character.

  一种结构，气味的关系上的低级同系物研究中的龙涎香气味物质okoumal与E1  CH 2  EL（3：埃尔= C; 4：埃尔= Si）或埃尔 ö 埃尔部分（5：埃尔= SI）为执行。合成了3 – 5的所有四种立体异构体，并通过气味描述和检测阈值进行了表征。测量了2 R配置的异构体的最低气味阈值，其中2 R，4 R配置为4 a（El = Si，X = CH 2）是该系列中最浓烈的，并且就其气味而言也是最好的。