2-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)propyl]-1H-isoindole-1,3(2H)-dione | 96056-26-7

• 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: 2-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)propyl]-1H-isoindole-1,3(2H)-dione
• 英文别名: 3-phthalimido-1-(triphenylphosphoranylidene)-2-oxopropane；1-phthalimido-3-(triphenylphosphoranylidene)-2-propanone；N-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)propyl]phthalimide；2-[2-Oxo-3-(triphenyl-lambda 5-phosphanylidene)-propyl]-1h-isoindole-1,3(2h)-dione；2-[2-oxo-3-(triphenyl-λ5-phosphanylidene)propyl]isoindole-1,3-dione
• CAS: 96056-26-7
• 化学式: C₂₉H₂₂NO₃P
• 分子量: 463.472
• InChiKey: KQPXVPAWLGHODZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)propyl]-1H-isoindole-1,3(2H)-dione 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 50.0h， 生成 1-phthalimido-4-[(N-phenylsulfonyl)-3-indolyl]-2-triisopropylsiloxy-1,3-butadiene
  参考文献：
  名称：

  1-Phthalimido-4-（3-吲哚基）-2-siloxy-1,3-丁二烯：合成和Diels–Alder反应性

  摘要：

  新的1-邻苯二甲酰亚胺-4-（3-吲哚基）-2-三烷基甲硅烷氧基-1,3-丁二烯很容易从1,3-二氯丙烷制得，其构型由NMR数据确定。研究了它们与不同的马来酰亚胺和醌的Diels-Alder反应性，通过X射线衍射研究证实，该化合物可得到高产率的exo环加合物。

  DOI：

  10.1016/j.tetlet.2003.12.118
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 在 乙醇 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 10.5h， 生成 2-[2-oxo-3-(triphenyl-λ⁵-phosphanylidene)propyl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis of Pyrrolizidinediones from CyclicN,N-Diacylamino Acids

  摘要：

  环状 N,N-二乙酰基氨基酸可通过与 N-苯基乙烯亚氨基三苯基膦反应转化为吡咯烷二酮。

  DOI：

  10.1246/cl.1986.1527

文献信息

• Synthesis and Evaluation of Ketophosph(on)ates as β-Lactamase Inhibitors
  作者：Senthil K. Perumal、R. F. Pratt

  DOI：10.1021/jo060364v

  日期：2006.6.1

  PhCH2OCONHCH(R)COCR‘N2. The electrophilicity of the carbonyl group in the resulting phosph(on)ates was assessed by the degree of hydration in aqueous solution, determined from NMR spectra. These compounds inhibited typical class C and class D β-lactamases, particularly the latter group, but showed no activity against class A enzymes. To enhance the carbonyl electrophilicity, an α-difluorinated analogue (R =

  一系列通式为PhCH 2 OCONHCH（R）COCHR'（CH 2）n（O）P（O 2 -）（O）R''（R = H，CH 3 ; R'= H，CH 3；n＝ 0，1； R′′＝ H，CH 3，Et，Ph）已经被制备作为β-内酰胺酶抑制剂的潜在来源。膦酸酯（n = 0）是通过Arbuzov反应获得的，而大多数磷酸盐则是通过磷酸（或/ on）酸与适当的重氮酮PhCH 2 OCONHCH（R）COCR'N 2的反应获得的。。通过由NMR光谱确定的水溶液中的水合度来评估所得的膦酸酯中羰基的亲电子性。这些化合物抑制典型的C类和D类β-内酰胺酶，特别是后者，但对A类酶没有活性。为了增强羰基亲电性，还制备了α-二氟类似物（R = H，CHR'= CF 2，n = 0，R''= Et），但是没有观察到增强的抑制活性。所有证据表明，这些化合物以羰基形式抑制，而不是通过在β-内酰胺酶活性位点形成四面体加合
• 1-Phthalimido-4-(3-indolyl)-2-siloxy-1,3-butadienes: synthesis and Diels–Alder reactivity
  作者：Esther Caballero、Dulce Alonso、Rafael Peláez、Concepción Alvarez、Pilar Puebla、Francisca Sanz、Manuel Medarde、Fernando Tomé

  DOI：10.1016/j.tetlet.2003.12.118

  日期：2004.2

  New 1-phthalimido-4-(3-indolyl)-2-trialkylsiloxy-1,3-butadienes were easily prepared from 1,3-dichloropropanone and their configurations were established from NMR data. Their Diels–Alder reactivity with different maleimides and quinones was studied, high yields of the exo cycloadducts being obtained, as confirmed by X-ray diffraction studies.

  新的1-邻苯二甲酰亚胺-4-（3-吲哚基）-2-三烷基甲硅烷氧基-1,3-丁二烯很容易从1,3-二氯丙烷制得，其构型由NMR数据确定。研究了它们与不同的马来酰亚胺和醌的Diels-Alder反应性，通过X射线衍射研究证实，该化合物可得到高产率的exo环加合物。
• Synthesis of Pyrrolizidinediones from Cyclic<i>N</i>,<i>N</i>-Diacylamino Acids
  作者：Hans Jürgen Bestmann、Thomas Moenius、Fouad Soliman

  DOI：10.1246/cl.1986.1527

  日期：1986.9.5

  Cyclic N,N-diacylami no acids can be converted by reaction with N-phenylketeniminylidenetriphenylphosphorane into pyrrolizidinediones.

  环状 N,N-二乙酰基氨基酸可通过与 N-苯基乙烯亚氨基三苯基膦反应转化为吡咯烷二酮。
• Folate analogs. 31. Synthesis of the reduced derivatives of 11-deazahomofolic acid, 10-methyl-11-deazahomofolic acid, and their evaluation as inhibitors of glycinamide ribonucleotide formyltransferase
  作者：M. G. Nair、B. R. Murthy、Sharadbala D. Patil、R. L. Kisliuk、J. Thorndike、Y. Gaumont、R. Ferone、D. S. Duch、M. P. Edelstein

  DOI：10.1021/jm00126a022

  日期：1989.6

  The Boon-Leigh procedure, involving condensation of a 6-chloro-5-nitropyrimidine (22) with an alpha-amino ketone (20 or 21) followed by reduction of the nitro group, cyclization, and L-glutamylation, led to the formation of 11-deazahomofolate (29) and its 10-methyl derivative (30). The corresponding (6R,S)-5,6,7,8-tetrahydro (4, 5) and 7,8-dihydro (31, 32) derivatives were prepared by catalytic hydrogenation. (6S)-11-Deazatetrahydrohomofolate was prepared from 29 by enzymatic reduction. Compounds 29 and 30 had little effect (IC50 greater than 2 x 10(-5) M) on Lactobacillus casei glycinamide ribonucleotide (GAR) formyltransferase but (6R,S)-11-deazatetrahydrohomofolate (4) is a potent inhibitor of this enzyme (IC50 = 5 x 10(-8) M). It is at least 100 times more inhibitory than 33, the 6S compound, indicating that the 6R component of the mixture having the unnatural configuration at C6 (34) is responsible for the potent inhibition. Compound 4 is a much weaker inhibitor of murine (L1210) and human (MOLT-4) leukemia cell GAR formyltransferases (IC50 greater than 1 x 10(-5) M). (6R,S)-11-Deaza-10-methyltetrahydrohomofolate (5) (IC50 = 1.1 x 10(-5) is 200 times weaker than 4 against L. casei GAR formyltransferase. However, 11-deaza-10-methyldihydrohomofolate (32) is more inhibitory (IC50 = 5.5 x 10(-7) M) than 5 or 30. None of the compounds showed inhibition of L. casei aminoimidazolecarboxamide ribonucleotide (AICAR) formyltransferase, dihydrofolate reductase, or thymidylate synthase. The dihydro derivatives 31 and 32 are 5% as active as dihydrofolate as substrates for L. casei dihydrofolate reductase. Compound 4 showed moderate inhibition of the growth of L. casei, Streptococcus faecium, MOLT-4 cells, and MCF-7 human breast adenocarcinoma cells.
• Folate analogs. 24. Syntheses of the antitumor agents 10-deazaaminopterin (10-DAAM) and 10-ethyl-10-deazaaminopterin (10-EDAAM)
  作者：M. G. Nair

  DOI：10.1021/jo00211a019

  日期：1985.5