2-(Diethylphosphono)butyronitrile | 34491-76-4

• 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
• 英文名称: 2-(Diethylphosphono)butyronitrile
• 英文别名: diethyl 1-cyanopropylphosphonate；(1-cyano-propyl)-phosphonic acid diethyl ester；(1-Cyan-propyl)-phosphonsaeure-diaethylester；2-Diaethoxyphosphinyl-butannitril；Diaethyl-1-cyano-propanphosphonat；2-Diethoxyphosphorylbutanenitrile
• CAS: 34491-76-4
• 化学式: C₈H₁₆NO₃P
• 分子量: 205.194
• InChiKey: ZTGBKXVQAMZVAI-UHFFFAOYSA-N

物化性质

• 沸点：
  119 °C(Press: 3 Torr)
• 密度：
  1.076 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-壬酮 、 2-(Diethylphosphono)butyronitrile 以81%的产率得到3-butyl-2-ethyl-hept-2-enenitrile
  参考文献：
  名称：

  Oxidative decyanation of secondary nitriles to ketones

  摘要：

  DOI：

  10.1021/jo00170a043
• 作为产物：
  描述：

  1-Brom-2-diethoxyphosphinyl-1-buten 在 sodium azide 作用下， 以 四氢呋喃 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(Diethylphosphono)butyronitrile
  参考文献：
  名称：

  α,β-不饱和羧酸衍生物。X. α-叠氮基-二乙氧基膦酰基-α-和β-烯烃的合成与反应

  摘要：

  α,β-二溴-β-二乙氧基膦基烷烃 (2) 是通过 β-二乙氧基膦酰基-α-烯烃的溴化反应获得的立体异构混合物（赤型：苏型 = 50 : 50），由 E-异构体和 Z -异构体（50：50）。发现 2 与叠氮化钠的反应立体选择性地进行，只得到 。α-溴-β-二乙氧基膦酰基-α-烯烃的 E-异构体，然后可以转化为 α-叠氮基-β-二乙氧基膦酰基-α-烯烃 (4) 和 α-叠氮基-β-二乙氧基膦酰基-β-烯烃，其构型由磷原子和乙烯基质子之间的耦合常数决定。此外，4的辐照产生了一种新型的β-二乙氧基膦酰基-α-烯烃-α-亚胺，随后重排成相应的腈。

  DOI：

  10.1246/bcsj.48.2891

文献信息

• Pyrido[2,3-d]pyrimidine-2,7-diamine kinase inhibitors
  申请人：——

  公开号：US20030073668A1

  公开（公告）日：2003-04-17

  Disclosed are compounds of the formula (I) wherein: R 2 , R 7 , RI 3 , R 14 and R 15 are independently hydrogen, or (un)substituted lower alkyl, (un)substitued lower alkenyl, (un)substituted lower alkynyl, or (un)substituted —(CH 2 ) n R 12 ; R 5 is halogen, cyano, nitro, —R 9 , —NR 9 R 10 , or —OR 9 ; R 6 is halogen, cyano, nitro, —R 9 , —NR 9 R 10 , —OR 9 , —Co 2 R 9 , —COR 9 , —CONR 9 R 10 , —NR 9 COR 10 , (un)substiuted lower alkenyl, or (un)substituted lower alkynyl; R 8 is —CO 2 R 13 , —COR 13 , —CONR 13 R 14 , —CSNR 13 R 14 , —C(NR 13 )NR 14 R 15 , —SO 3 R 13 , —SO 2 R 13 , —SO 2 NR 13 R 14 , —PO 3 R 13 R 14 , —POR 13 R 14 , —PO(NR 13 R 14 ) 2 ; R 9 and R 10 are independently hydrogen or (un)substituted lower alkyl; R 11 is a heteroaryl or a heterocyclic group; R 12 is a cycloalkyl, a heterocyclic, an aryl, or a heteroaryl group; and n is 0,1,2, or 3. These compounds and their pharmaceutical compositions are useful for treating cell proliferative disorders, such as cancer and restenosis. These compounds are potent inhibitors of cdks and growth factor-mediated kinases.

  披露了公式(I)的化合物，其中：R2、R7、R13、R14和R15独立为氢，或（未）取代的低烷基，（未）取代的低烯基，（未）取代的低炔基，或（未）取代的—(CH2)nR12；R5为卤素，氰基，硝基，—R9，—NR9R10，或—OR9；R6为卤素，氰基，硝基，—R9，—NR9R10，—OR9，—Co2R9，—COR9，—CONR9R10，—NR9COR10，（未）取代的低烯基，或（未）取代的低炔基；R8为—CO2R13，—COR13，—CONR13R14，—CSNR13R14，—C(NR13)NR14R15，—SO3R13，—SO2R13，—SO2NR13R14，—PO3R13R14，—POR13R14，—PO(NR13R14)2；R9和R10独立为氢或（未）取代的低烷基；R11为杂芳基或杂环基团；R12为环烷基，杂环，芳基，或杂芳基团；n为0,1,2,或3。这些化合物及其药物组合物可用于治疗细胞增殖障碍，如癌症和再狭窄。这些化合物是cdks和生长因子介导激酶的强效抑制剂。
• Carbanionic displacement reactions at phosphorus. Part III. Cyanomethylphosphonate vs. cyanomethylenediphosphonate. Synthesis and solid-state structures
  作者：Bogdan Iorga、Louis Ricard、Philippe Savignac

  DOI：10.1039/b003371p

  日期：——

  The results of the carbanionic reaction between acetonitrile and chlorophosphates depend strongly on the nature of the metallating agent (LiTMP, LDA, LiHMDS). According to the nature of the base, the reaction can be directed towards the formation of either cyanomethylphosphonates 3 or cyanomethylenediphosphonates 5. Electrophilic halogenation of lithiated cyanomethylphosphonate 2a leads to the mono-chloro 17, -bromo 18 and -iodo 19 derivatives. Only the monochloro product 17 is stable enough to be isolated in pure form. The structures of cyanobenzylphosphonate 10b, cyanomethylenediphosphonate 5b and its corresponding lithiated carbanion 4b are determined by X-ray crystallography. The polymeric structure, coupled with a wide charge delocalization, without C–Li contacts, is in agreement with the lack of reactivity towards electrophiles.

  乙腈与氯膦酸酯之间的负碳阴离子反应结果在很大程度上依赖于金属化试剂的性质（LiTMP, LDA, LiHMDS）。根据碱的性质，反应可以定向生成氰基甲基膦酸酯 3 或氰基亚甲基二膦酸酯 5。锂化的氰基甲基膦酸酯 2a 的亲电卤素化反应会导致单氯 17、单溴 18 和单碘 19 衍生物的生成。只有单氯产品 17 稳定到足以以纯形式分离出来。通过X射线晶体学确定了氰基苄基膦酸酯 10b、氰基亚甲基二膦酸酯 5b 及其相应的锂化负碳阴离子 4b 的结构。聚合结构，以及宽广的电荷去局域化，没有 C–Li 接触，这与缺乏对亲电体反应性的情况是一致的。
• The total synthesis of (−)-suaveoline
  作者：Patrick D. Bailey、Keith M. Morgan

  DOI：10.1039/b005695m

  日期：——

  A new synthesis of the indole alkaloid (−)-suaveoline from L-tryptophan is reported (overall yield ca. 14%). Key synthetic steps include a high yielding cis-specific Pictet–Spengler reaction, a one-pot Horner–Wadsworth–Emmons and alkylation procedure, a vinylogous Thorpe cyclisation and the direct formation of a 3,4,5-trisubstituted pyridine from a 1,5-dinitrile. The direct conversion of ajmaline to

  的新综合 吲哚生物碱 （-）-suaveoline来自 L-色氨酸据报道（总收率约为14％）。关键的合成步骤包括高产量的顺式Pictet-Spengler反应，一锅Horner-Wadsworth-Emmons和烷基化 程序，乙烯基索普 环化 并直接形成3,4,5-三取代 吡啶从1，5-二苯胺。直接转换阿玛琳 还描述了半合成的suaveoline。
• Use of β-Chloropropionaldehyde as an Acrolein Equivalent in the Wadsworth-Emmons Modification of the Wittig Reaction
  作者：Kohtaro Tomizawa、David S. Watt、George R. Lenz

  DOI：10.1055/s-1985-31373

  日期：——

  ß-Chloropropionaldehyde (3) has been used as an acrolein equivalent to prepare 5-chloro-2-pentenoates 5 and 5-chloro-2-pentenenitriles 6 by condensing with phosphonates 1.

  ß-氯丙醛（3）被用作丙烯醛的等价物，通过与膦酸盐 1 缩合，制备 5-氯-2-戊烯酸盐 5 和 5-氯-2-戊烯腈 6。
• Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoprotein sites
  申请人：WOCKHARDT LIMITED

  公开号：US20040063954A1

  公开（公告）日：2004-04-01

  The present invention provides agents having high antimicrobial activity for preventing and treating infectious diseases. Thus, the present invention provides novel cyano-(substituted)-methylenepiperidinophenyl oxazolidinone derivatives, processes for making the compounds, as well as antimicrobial compositions containing said derivatives as active ingredients and methods of treating bacterial infections with the said derivatives.

  本发明提供了具有高抗微生物活性的代理，用于预防和治疗传染病。因此，本发明提供了新型的氰基-（取代）-亚甲基哌啶基苯氧唑烷衍生物、制备该化合物的方法，以及包含该衍生物作为活性成分的抗微生物组合物和使用该衍生物治疗细菌感染的方法。