2-pentylheptene oxide | 120289-64-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2-pentylheptene oxide
• 英文别名: 2,2-Dipentyloxirane
• CAS: 120289-64-7
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: AXOZWSUFOMUTJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  230.7±8.0 °C(Predicted)
• 密度：
  0.849±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-pentylheptene oxide 在 palladium on activated charcoal 硫酸 、 三氟化硼乙醚 、 氢气 作用下， 以 乙酸乙酯 、 苯 为溶剂， 5.0~25.0 ℃ 、344.73 kPa 条件下， 反应 15.02h， 生成 4,4 dipentylcyclohexanone
  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：

  二正戊基酮 、 三甲基碘化亚砜 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成 2-pentylheptene oxide
  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

• A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C–C Bond Cleavage Reactions
  作者：Eisuke Ota、Huaiju Wang、Nils Lennart Frye、Robert R. Knowles

  DOI：10.1021/jacs.8b12552

  日期：2019.1.30

  We report a general protocol for the light-driven isomerization of cyclic aliphatic alcohols to linear carbonyl compounds. These reactions proceed via proton-coupled electron-transfer activation of alcohol O-H bonds followed by subsequent C-C β-scission of the resulting alkoxy radical intermediates. In many cases, these redox-neutral isomerizations proceed in opposition to a significant energetic gradient

  我们报告了光驱动的环状脂肪醇异构化为线性羰基化合物的通用协议。这些反应通过醇 OH 键的质子耦合电子转移活化进行，随后生成的烷氧基自由基中间体的 CC β 断裂。在许多情况下，这些氧化还原中性异构化与显着的能量梯度相反，产生的产品热力学稳定性低于起始材料。提出了一种机制来合理化这种不平衡行为，该机制可以作为设计由激发态氧化还原事件驱动的其他逆热力学转换的模型。
• One-Pot Synthesis of<i>N</i>-<i>tert</i>-Butylsulfinylimines and Homoallylamine Derivatives from Epoxides
  作者：Alejandro Lahosa、Francisco Foubelo、Miguel Yus

  DOI：10.1002/ejoc.201600612

  日期：2016.8

  The reaction of epoxides with tert-butanesulfinamide in the presence of a Lewis acid, such as erbium triflate or boron trifluoride–diethyl ether, in THF as solvent, under microwave or thermal activation, produces N-tert-butylsulfinylimines in reasonable yields. Aromatic and gem-disubstituted and trisubstituted alkyl epoxides performed better than mono-alkyl-substituted compounds. After imine formation

  环氧化物与叔丁烷亚磺酰胺在路易斯酸（如三氟甲磺酸铒或三氟化硼 - 乙醚）存在下，以 THF 为溶剂，在微波或热活化下反应，以合理的产率生成 N-叔丁基亚磺酰亚胺。芳香族和双取代和三取代的烷基环氧化物比单烷基取代的化合物表现更好。亚胺形成后，随后的铟促进的烯丙基化可以在同一反应烧瓶中以单一合成操作进行，从而以通常高的产率得到高烯丙胺衍生物。
• Straight and versatile synthesis of substituted perhydrofuro[2,3-b]pyrans from 2-chloromethyl-3-(2-methoxyethoxy)propene
  作者：Francisco Alonso、Emilio Lorenzo、Jaisiel Meléndez、Miguel Yus

  DOI：10.1016/s0040-4020(03)00781-6

  日期：2003.7

  powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1=R1R2CO) in THF at −78 to 0°C, followed by the addition of an epoxide [E2=R3R4C(O)CHR5] at 0 to 20°C leads, after hydrolysis, to the expected methylidenic diols. These diols when subjected to successive hydroboration–oxidation and further oxidation, spontaneous cyclization occurs to furnish a series of differently

  2-氯甲基-3-（2-甲氧基乙氧基）丙烯与过量的锂粉和催化量的萘（2.5％）在羰基化合物（E 1 = R 1 R 2 CO）存在下于THF中反应在-78至0℃下，在水解后，在0至20℃下添加环氧化物[E 2＝ R 3 R 4 C（O）CHR 5 ]，得到预期的亚甲基二醇。这些二醇经过连续的硼氢化-氧化和进一步的氧化后，会发生自发环化，从而提供一系列不同取代的全氢呋喃[2,3- b ]吡喃。
• Highly selective ring opening of epoxides with silicon tetrafluoride: Preparation of fluorohydrins
  作者：Makoto Shimizu、Hirosuke Yoshioka

  DOI：10.1016/s0040-4039(00)80427-x

  日期：1988.1

  Regio-, stereo-, and chemoselective transformation of epoxides into fluorohydrins with silicon tetrafluoride is described.

  描述了用四氟化硅将环氧的区域，立体和化学选择性转化为氟代醇。
• Regioselective synthesis of 1,7-dioxaspiro[4.4]nonanes from a trimethylenemethane dianion synthon
  作者：Francisco Alonso、Bruno Dacunha、Jaisiel Meléndez、Miguel Yus

  DOI：10.1016/j.tet.2004.10.101

  日期：2005.3

  2-Chloromethyl-3-(2-methoxyethoxy)prop-1-ene behaves as a versatile trimethylenemethane dianion synthon, precursor of a variety of methylidenic diols obtained by DTBB-catalysed lithiation in the presence of a carbonyl compound (E1=R1R2CO) in THF at −78 to 0 °C, followed by the addition of an epoxide [E2=R3R4C(O)CHR5] at 0 to 20 °C and final hydrolysis. These diols undergo double intramolecular iodoetherification

  2-氯甲基-3-（2-甲氧基乙氧基）丙-1-烯的行为是多用途的三亚甲基二价阴离子合成子，它是在羰基化合物存在下通过DTBB催化锂化获得的各种亚甲基二醇的前体（E 1 = R 1 R 2 CO）在-78至0°C下的THF中，然后加入环氧化物[E 2 = R 3 R 4 C（O）CHR 5在0至20℃下进行最终水解。这些二醇在碘和氧化银（I）的存在下于THF或二氧六环-水中进行双分子碘化醚化反应，生成相应的1,7-二氧杂螺[4.4]壬烷，可以很容易地氧化成各种1,7 -dioxaspiro [4.4] nonan-6-ones。这些骨骼存​​在于多种天然产物中。