二乙基[2-(异丁基氨基)-2-氧代乙基]膦酸酯 | 62872-62-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 中文名称: 二乙基[2-(异丁基氨基)-2-氧代乙基]膦酸酯
• 英文名称: diethyl (2-(isobutylamino)-2-oxoethyl)phosphonate
• 英文别名: N-Isobutyl diethylphosphonoacetamide；2-diethoxyphosphoryl-N-(2-methylpropyl)acetamide
• CAS: 62872-62-2
• 化学式: C₁₀H₂₂NO₄P
• 分子量: 251.263
• InChiKey: FQAYSONYHAHHRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  388.9±25.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二乙基[2-(异丁基氨基)-2-氧代乙基]膦酸酯 在 正丁基锂 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-3-((2R,3S)-3-Chloromethyl-tetrahydro-pyran-2-yl)-N-isobutyl-acrylamide
  参考文献：
  名称：

  合成子可合成天然杀虫脂质异丁酰胺

  摘要：

  描述了通向一般酰胺合成子（4）的四种途径。还制备了适用于与天然异丁酰胺的其他基团相似的方法的合成子（33，R ＝ H）和（36）。

  DOI：

  10.1016/s0040-4039(00)94858-5
• 作为产物：
  描述：

  二乙基磷乙酸 在 草酰氯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 二乙基[2-(异丁基氨基)-2-氧代乙基]膦酸酯
  参考文献：
  名称：

  METHOD FOR PRODUCING SANSHOOL

  摘要：

  提供一种生产花椒醇的方法，该方法具有简短的过程并表现出高立体选择性，以及一种铁羰基络合物化合物，该化合物是用于生产方法的中间体。一种二烯铁络合物化合物，其特征在于由以下一般式(I)表示：（其中A代表CO、P(RA)3、CN、NO、SO(RA)3或N(RA)2；RA代表具有1至4个碳原子的直链或支链烷基基团或具有6至12个碳原子的芳基基团；R1和R2中的一个代表氢原子，另一个代表以下式(I)表示的结构）：（其中R代表氢原子、羟基或甲基）。

  公开号：

  US20130245303A1

文献信息

• Effect of Asiasarum Root Extract and Its Constituents on Interleukin-1β-Stimulated Matrix Metalloproteinase-1 Secretion from Human Gingival Fibroblasts
  作者：Megumi Futamura-Masuda、Mami Yokota-Honda、Takuya Anraku、Kanae Nakanishi、Kazuya Murata、Tetsuro Shinada、Hideaki Matsuda

  DOI：10.1248/bpb.b15-01000

  日期：——

  Asiasarum root (roots and rhizome of Asiasarum sieboldii or A. heterotropoides var. mandshuricum) has been frequently used in traditional Chinese medicinal formulas for the management of oral malodor syndrome caused by periodontal disease. However, there are no scientific reports concerning these effects and the mechanism of action. The objective of this study was to examine the inhibitory effects of Asiasarum root and its constituents on oral malodor syndrome and periodontal disease. A 50% ethanolic extract of Asiasarum root (AR-ext) showed L-methionine γ-lyase (METase) inhibitory activity at a concentration of 200 µg/mL, and inhibited interleukin (IL)-1β-stimulated matrix metalloproteinase (MMP)-1 secretion from human gingival fibroblasts (HGFs) at a concentration of 10 and 50 µg/mL without cytotoxic effects. Activity-guided fractionation of the AR-ext suggested that METase inhibitory activity was attributable to a mixture of linoleic and oleic acid, because these unsaturated fatty acids showed weak METase inhibitory activities. Similar fractionation using MMP-1 secretion inhibitory activity led to the isolation of two unsaturated fatty acid amides, (2E,4E,8Z,10E)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide (1) and (2E,4E,8Z,10Z)-N-(2-methylpropyl)dodeca-2,4,8,10-tetraenamide (2), as active constituents with inhibitory activity on MMP-1 secretion from HGFs. To elucidate the inhibition mechanism on MMP-1 secretion, the effect of 2 on mitogen-activated protein kinase (MAPK) phosphorylation was examined. Western blotting analysis revealed that 2 (10 µM) reduced the phosphorylation of p38 and c-Jun-N-terminal kinase. These results suggested that 2 suppresses intracellular MMP-1 expression and MMP-1 secretion from IL-1β-stimulated HGFs by down-regulation of MAPK phosphorylation.

  细辛根(Asiasarum sieboldii或A. heterotropoides var. mandshuricum的根和根茎)在传统中药方剂中常用于治疗由牙周病引起的口腔异味综合征。然而，目前尚缺乏关于这些效果及其作用机制的科学报告。本研究旨在探讨细辛根及其成分对口腔异味综合征和牙周病的抑制作用。细辛根的50%乙醇提取物(AR-ext)在200 µg/mL浓度下显示出L-蛋氨酸γ-裂解酶(METase)抑制活性，并在10和50 µg/mL浓度下抑制人牙龈成纤维细胞(HGFs)中白细胞介素(IL)-1β刺激的基质金属蛋白酶(MMP)-1的分泌，且无细胞毒性作用。活性导向的AR-ext分级分离表明，METase抑制活性归因于亚油酸和油酸的混合物，因为这些不饱和脂肪酸显示出较弱的METase抑制活性。类似的利用MMP-1分泌抑制活性的分级分离，得到了两种不饱和脂肪酸酰胺，即(2E,4E,8Z,10E)-N-(2-甲基丙基)十二碳-2,4,8,10-四烯酰胺(1)和(2E,4E,8Z,10Z)-N-(2-甲基丙基)十二碳-2,4,8,10-四烯酰胺(2)，它们作为活性成分具有抑制HGFs中MMP-1分泌的作用。为了阐明对MMP-1分泌的抑制机制，研究了2对丝裂原活化蛋白激酶(MAPK)磷酸化的影响。Western blot分析显示，2(10 µM)减少了p38和c-Jun氨基末端激酶的磷酸化。这些结果表明，2通过下调MAPK磷酸化，抑制了IL-1β刺激的HGFs中细胞内MMP-1表达和MMP-1的分泌。
• A Powerful Hydrogen-Bond-Donating Organocatalyst for the Enantioselective Intramolecular Oxa-Michael Reaction of α,β-Unsaturated Amides and Esters
  作者：Yusuke Kobayashi、Yamato Taniguchi、Noboru Hayama、Tsubasa Inokuma、Yoshiji Takemoto

  DOI：10.1002/anie.201305492

  日期：2013.10.11

  Tuning the organocatalyst: An unprecedented enantioselective intramolecular oxa‐Michael reaction of unactivated α,β‐unsaturated amides and esters catalyzed by a powerful hydrogen‐bond‐donating organocatalyst has been developed. Furthermore, the products obtained from this reaction have been used for the straightforward asymmetric synthesis of several natural products and biologically important compounds

  调节有机催化剂：已开发出前所未有的对映体选择性分子内氧杂-Michael反应，该反应由强大的给氢键有机催化剂催化，未活化的α，β-不饱和酰胺和酯。此外，从该反应获得的产物已经用于几种天然产物和生物学上重要的化合物的直接不对称合成。
• A new approach for the total synthesis of spilanthol and analogue with improved anesthetic activity
  作者：Isabella G. Alonso、Lais T. Yamane、Verônica S. de Freitas-Blanco、Luiz F.T. Novaes、Michelle Franz-Montan、Eneida de Paula、Marili V.N. Rodrigues、Rodney A.F. Rodrigues、Julio C. Pastre

  DOI：10.1016/j.tet.2018.06.034

  日期：2018.9

  A 5-step synthesis of spilanthol (affinin) is reported, where the route features complete control of alkene geometry during the assembling of the double bonds, with the use of a Sonogashira cross-coupling reaction, a Z-selective alkyne semi-reduction and a HWE olefination reaction as the key steps. A simplified analogue was also prepared in 4 steps. Both compounds were found to permeate dermatomed

  据报道，由五步合成了香薄荷醇（亲和素），该路线的特征是在双键组装过程中通过Sonogashira交叉偶联反应，Z选择性炔烃半还原和完全控制烯烃几何构型。 HWE烯烃化反应是关键步骤。还分四个步骤制备了简化的类似物。发现这两种化合物都通过体外Franz型扩散池渗透到有皮的猪耳朵皮肤中。简化类似物呈现优异的麻醉效果的体内，使用甩尾模型相比时，千日菊酰胺和市售的标准EMLA ®。这些结果表明，斯皮兰特及其类似物均可用作临床实践中的局部麻醉剂。
• Arylfluoroalkenamides and their use as pesticides
  申请人：ROUSSEL UCLAF

  公开号：EP0346107A2

  公开（公告）日：1989-12-13

  Compound of the formula (I): or a salt thereof, wherein Q1 is a monocyclic or a fused bicyclic ring system each ring containing 5 or 6 ring atoms selected from carbon and optionally one or more heteroatoms at least 1 ring being aromatic, or Q1 is a dihalovinyl group; Q is an alkyl chain containing 1 to 12 carbon atoms and optionally containing one or two oxygen atoms and/or an unsaturated group -CR7 = CR8-, or -C=C-, wherein R7 and R8 are selected from hydrogen or halo; a is 0 or 1; b is O or 1; the sum of a and b is O or 1; R2, R3, R4, R5 and R6 are the same or different, and are independently selected from hydrogen, halo and C1-4 alkyl; R1 is selected from hydrogen and C1-6 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C1-6 alkoxy are disclosed which have pesticidal activity. Pesticidal formulations containing the compounds of the formula (I), their use in the control of pests and methods for their preparation are also disclosed.

  式(I)化合物： 或其盐，其中 Q1 是单环或融合双环系统，每个环含有 5 或 6 个选自碳的环原子和任选的一个或多个杂原子，至少有一个环是芳香族环，或 Q1 是二卤代乙烯基；Q 是含有 1 至 12 个碳原子的烷基链，任选含有一个或两个氧原子和/或不饱和基团 -CR7 = CR8-，或 -C=C-，其中 R7 和 R8 选自氢或卤代；a为0或1；b为O或1；a和b之和为O或1；R2、R3、R4、R5和R6相同或不同，且独立选自氢、卤代和C1-4烷基；R1选自氢和任选被二噁烷基、卤代、氰基、三氟甲基、三氟甲硫基或C1-6烷氧基取代的C1-6烃基。还公开了含有式（I）化合物的杀虫制剂、其在防治害虫中的用途及其制备方法。
• Pesticides
  申请人：ROUSSEL-UCLAF

  公开号：EP0369762A1

  公开（公告）日：1990-05-23

  The present Application discloses pesticidally active compounds of the formula (I): or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each optionally substituted, or Q is a dihalovinyl group or a group R6-C≡C- where R6 is C1 -4 alkyl, tri C1-4. alkylsilyl, halogen or hydrogen; Q1 is a 1,2-cyclopropyl ring optionally substituted by one or more groups selected from C1 -a alkyl, halo, C1-3 haloalkyl, alkynyl, or cyano; R2,R3, R4 and R5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C1 -4 alkyl or C1 -4 haloalkyl; X is oxygen or sulphur; and R1 is selected from hydrogen and C1 -8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifuoromethyl, trifluoromethylthio or C1-6 alkoxy, their preparation, pesticidal compositions containing them and their use against pests.

  本申请公开了式 (I) 的农药活性化合物： 或其盐，其中 Q 是单环芳香环或融合双环系统，其中至少一个环是芳香环，包含 9 或 10 个原子，其中一个原子可以是氮原子，其余的碳原子各自被任选取代，或者 Q 是二卤代乙烯基或基团 R6-C≡C-，其中 R6 是 C1 -4 烷基、三 C1-4.烷基硅烷基、卤素或氢；Q1 是被一个或多个选自 C1 -a 烷基、卤素、C1-3 卤代烷基、炔基或氰基的基团任选取代的 1,2-环丙基环；R2、R3、R4 和 R5 相同或不同，其中至少一个是氢，其他的独立选自氢、卤素、C1 -4 烷基或 C1 -4 卤代烷基；X 是氧或硫；R1 选自氢和任选被二噁烷基、卤代、氰基、三氟甲基、三氟甲硫基或 C1-6 烷氧基取代的 C1-8 碳氢基。