4-n-decylcyclohex-2-en-1-one | 98789-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-n-decylcyclohex-2-en-1-one
• 英文别名: 4-Decyl-2-cyclohexen-1-one；4-Decylcyclohex-2-en-1-one
• CAS: 98789-94-7
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: KSBYAVIMRXZXSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  4-n-decylcyclohex-2-en-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 4-癸基环己酮
  参考文献：
  名称：

  Antiarthritic and supressor cell inducing activity of azaspiranes: structure-function relationships of a novel class of immunomodulatory agents

  摘要：

  Spirogermanium (1; 8,8-diethyl-N,N-dimethyl-2-aza-8- germaspiro[4.5]decane-2-propanamine dihydrochloride) is a potent cytotoxic agent in vitro which has demonstrated limited activity in experimental animal tumor models. Subsequently, it has been reported that spirogermanium has antiarthritic and suppressor cell-inducing activity. We have synthesized a series of substituted 8-hetero-2-azaspiro[4.5]decane and 9-hetero-3-azaspiro[5.5]undecane analogues of spirogermanium to identify the heteroatom requirements for in vivo antiarthritic and suppressor cell-inducing activity. This structure-activity relationship study has identified that appropriately substituted silicon and carbon analogues of spirogermanium retain both antiarthritic and immunosuppressive activity, with the 8,8-dipropyl (carbon) analogue being among the most active. Following the identification of N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride (9) as a more active analogue than spirogermanium, a series of 8,8-dipropyl analogues with various amine substituents were synthesized. A number of these analogues had activity similar to that of 9. A correlation between activity in the adjuvant arthritic rat and the ability to induce suppressor cells (r = 0.894, p less than 0.001) suggests an association between the two pharmacologic effects. While the precise biochemical mechanism(s) for the pharmacological activity is unclear, these data suggest that compounds within this series, e.g., N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride, may provide effective therapy in diseases of autoimmune origin and/or the prevention of rejection in tissue transplantation.

  DOI：

  10.1021/jm00173a010
• 作为产物：
  描述：

  十一醛 在 硫酸 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 15.02h， 生成 4-n-decylcyclohex-2-en-1-one
  参考文献：
  名称：

  Antiarthritic and supressor cell inducing activity of azaspiranes: structure-function relationships of a novel class of immunomodulatory agents

  摘要：

  Spirogermanium (1; 8,8-diethyl-N,N-dimethyl-2-aza-8- germaspiro[4.5]decane-2-propanamine dihydrochloride) is a potent cytotoxic agent in vitro which has demonstrated limited activity in experimental animal tumor models. Subsequently, it has been reported that spirogermanium has antiarthritic and suppressor cell-inducing activity. We have synthesized a series of substituted 8-hetero-2-azaspiro[4.5]decane and 9-hetero-3-azaspiro[5.5]undecane analogues of spirogermanium to identify the heteroatom requirements for in vivo antiarthritic and suppressor cell-inducing activity. This structure-activity relationship study has identified that appropriately substituted silicon and carbon analogues of spirogermanium retain both antiarthritic and immunosuppressive activity, with the 8,8-dipropyl (carbon) analogue being among the most active. Following the identification of N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride (9) as a more active analogue than spirogermanium, a series of 8,8-dipropyl analogues with various amine substituents were synthesized. A number of these analogues had activity similar to that of 9. A correlation between activity in the adjuvant arthritic rat and the ability to induce suppressor cells (r = 0.894, p less than 0.001) suggests an association between the two pharmacologic effects. While the precise biochemical mechanism(s) for the pharmacological activity is unclear, these data suggest that compounds within this series, e.g., N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride, may provide effective therapy in diseases of autoimmune origin and/or the prevention of rejection in tissue transplantation.

  DOI：

  10.1021/jm00173a010

文献信息

• Phase behavior of some mono-substituted ferrocene- and [3]ferrocenophane-containing nematics with the cyclohexane ring in the rigid core
  作者：So Yeon Kim、Oleg N. Kadkin、Eun Ho Kim、Moon-Gun Choi

  DOI：10.1016/j.jorganchem.2011.03.013

  日期：2011.6

  unbridged ferrocene. Depending on thermal prehistory of the samples, some of the synthesized ferrocenomesogens showed remarkable migration of the phase transition temperatures. In one case such behavior led to stabilization of the initially monotropic nematic mesophase in subsequent heating cycles. In another case, the phase transition shifts caused the lowering of the crystal-to-nematic transition temperature

  通常，将环己烷环结合到棒状介晶的刚性核中导致改善的技术参数，即低粘度，环境转变温度和向列态的稳定性。考虑到这一点，已经合成了一系列新颖的含二茂铁的含环己烷的衍生物。已经研究了各种结构因素对合成的含二茂铁的向列型液晶行为的影响。与未桥联的二茂铁的衍生物相比，二茂铁的化合物显示出增强的液晶性能。根据样品的热史，一些合成的铁茂铁致病菌表现出明显的相变温度迁移。在一种情况下，这种行为导致随后的加热循环中最初的单向性向列中间相稳定。在另一种情况下，相变位移引起晶体向向列相转变温度的降低和中间相范围的扩大。从最初的对映行为到单向行为也有变化。所获得的新型金属成因剂是向具有发色，可氧化还原转换，可极化和化学稳定的超芳族二茂铁单元的液晶应用低粘度和低温材料发展的重要脚步。从最初的对映行为到单向行为也有变化。所获得的新型金属成因剂是向具有发色，可氧化还原转换，可极化和化学稳定的超芳族二茂铁单元的液晶应用低粘
• Novel Tetrahedratic Smectic C and Nematic Mesophases in Unsymmetrically 1,1′-Bis-substituted Ferrocenomesogens
  作者：Oleg N. Kadkin、Eun Ho Kim、Young Joon Rha、So Yeon Kim、Jigeon Tae、Moon-Gun Choi

  DOI：10.1002/chem.200901349

  日期：2009.10.12

  Non‐conventional mesophases have been observed in novel ferrocene‐containing liquid crystals. The formation of helical and garland‐like superstructures, and spontaneous resolution into macroscopic chiral domains occur in the lamellar mesophase. The nematic mesophase shows unusual textures and chiral nematic droplets such as those depicted.

  在新型的含二茂铁的液晶中已经观察到非常规的中间相。层状中间相发生了螺旋状和花环状的超结构的形成，并自发地分解为宏观的手性域。向列中间相显示出异常的质地和手性向列液滴，如所描绘的。
• Novel synthesis of trans-hydroindenones by thermal reaction of α,ω-bis(diazo)diketones
  作者：Kazuhiko Nakatani、Kazunori Takada、Yoshihiko Odagaki、Sachihiko Isoe

  DOI：10.1039/c39930000556

  日期：——

  Thermal reaction of α,ω-bis(diazo)diketones gives αβ-unsaturated cycloalkenones including unsubstituted trans-hydroindenones, which were difficult to access by the conventional synthetic reactions.

  δ±，Ï-双（重氮）二酮的热反应产生了δ±²-不饱和环烯酮，包括未取代的反式氢茚酮，这些物质很难通过传统合成反应获得。
• Intramolecular Cooperative Reactions of 1,2-Bis(diazoketone)s. The First Syntheses of trans-Hydro-1H-2-inden-1-ones
  作者：Kazuhiko Nakatani、Kazunori Takada、Sachihiko Isoe

  DOI：10.1021/jo00113a030

  日期：1995.4

  The intramolecular cooperative reactions of 1,2-bis(diazoketone)s initiated by the Wolff rearrangement of alpha-diazoketones have been investigated. Under thermal conditions, 1,2-bis(diazoketone)s are efficiently transformed into 2-cyclopenten-1-one derivatives with complete stereospecificity. Thus, a most extraordinary result is reported, that trans-hydro-2-inden-1-ones (1-3) were synthesized for the first time from trans-1,2-bis(diazoketone)s (5, 11, and 12), respectively. The unprecedented trans-hydroindenone structure was confirmed by X-ray analysis of 3 as well as H-1 NMR analysis and was supported by ab initio molecular orbital calculations. The same reactions were also carried out under photochemical conditions and were applied to 1,3-bis(diazoketone)s, giving 2-cyclohexen-1-one derivatives.
• Sucrow, Wolfgang; Minas, Hermann; Stegemeyer, Horst, Chemische Berichte, 1985, vol. 118, # 8, p. 3332 - 3349
  作者：Sucrow, Wolfgang、Minas, Hermann、Stegemeyer, Horst、Geschwinder, Peter、Murawski, Hans-Ruediger、Krueger, Carl

  DOI：——

  日期：——