diethyl (2-chloroacetyl)phosphonate | 25196-02-5

• 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: diethyl (2-chloroacetyl)phosphonate
• 英文别名: chloroacetyl-phosphonic acid diethyl ester；Chloracetyl-phosphonsaeure-diaethylester；Diethyl (chloroacetyl)phosphonate；2-chloro-1-diethoxyphosphorylethanone
• CAS: 25196-02-5
• 化学式: C₆H₁₂ClO₄P
• 分子量: 214.586
• InChiKey: SVBGKKZSTJWETC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (2-chloroacetyl)phosphonate 生成 (NE)-N-(2-chloro-1-diethoxyphosphorylethylidene)hydroxylamine
  参考文献：
  名称：

  TANEJA, H. K.;ROY, N. K., J. INST. CHEM., 61,(1989) N, C. 28-30

  摘要：

  DOI：
• 作为产物：
  描述：

  diethoxyphosphoryldichloroacetaldehyde 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 7.0h， 生成 diethyl (2-chloroacetyl)phosphonate
  参考文献：
  名称：

  Guseinov; Klimentova; Kol'tsova, Russian Journal of General Chemistry, 1996, vol. 66, # 3, p. 441 - 443

  摘要：

  DOI：

文献信息

• Regioselective Synthesis of Novel Functionalized Pyrano[2′,3′:4,5]pyrimido[1,6-b][1,2,4,5]triazaphosphepines
  作者：T. E. Ali、M. A. Assiri、I. S. Yahia、H. Y. Zahran、M. H. Meselhy、M. S. A. Hussien

  DOI：10.1134/s1070428021010115

  日期：2021.1

  Abstract The reactions of 6-acetyl-3-amino-4-imino-7-methyl-5-phenyl-3,5-dihydro-4H-pyrano[2,3-d]pyrimidine with triethyl phosphite and some electrophilic reagents, namely 1,2-dibromoethane, oxalyl chloride, chloroacetyl chloride, and ethyl chloroacetate, were studied. These one-pot three-component reactions regioselectively afforded four new 11-acetyl-2-ethoxy-10-methyl-12-phenylpyrano[2′,3′:4,5]pyrimido[1

  摘要 6-乙酰基-3-氨基-4-亚氨基-7-甲基-5-苯基-3,5-二氢-4 H-吡喃并[2,3- d ]嘧啶与亚磷酸三乙酯和某些亲电试剂的反应研究了1,2-二溴乙烷，草酰氯，氯乙酰氯和氯乙酸乙酯。这些一锅三组分反应区域选择性地提供了四个新的11-乙酰基-2-乙氧基-10-甲基-12-苯基吡喃并[2'，3'：4,5]嘧啶并[1,6- b ] [1,2 ，4,5λ 5 ] triazaphosphepin -2-酮在69-73％的产率。
• A NEW METHOD FOR ACYLATION OF ENOLATES BY MEANS OF DIALKYL ACYLPHOSPHONATES AS ACYLATING AGENTS
  作者：Mitsuo Sekine、Akiko Kume、Masashi Nakajima、Tsujiaki Hata

  DOI：10.1246/cl.1981.1087

  日期：1981.8.5

  Acylations of various enolates by means of diethyl acylphosphonates were described. For the acylation of acetophenone, lithium bis(trimethylsilyl)amide (LSA) was found to be suitable as the base. The scope and limitation of the benzoylation using diethyl benzoylphosphonates were also described.

  描述了通过酰基膦酸二乙酯对各种烯醇化物的酰化。对于苯乙酮的酰化，发现双（三甲基甲硅烷基）氨基锂（LSA）适合作为碱。还描述了使用苯甲酰膦酸二乙酯进行苯甲酰化的范围和限制。
• Synthesis and Biological Activities of Some New Phosphorus Compounds Containing Pyranopyrazole Moiety
  作者：Tarik E. Ali、Mohammed A. Assiri、Hafez M. El-Shaaer、Somaya M. El-Edfawy、Noha M. Hassanin、Ali A. Shati、Mohammad Y. Alfaifi、Serag Eldin I. Elbehairi、Somaia M. Abed-Kariem

  DOI：10.3987/com-21-14448

  日期：——

  properties. Compound 7 displayed promising antimicrobial and antioxidative properties. Also, compound 8 showed potent cytotoxic effects against MCF-7, HepG-2 and HCT-116 cancer cells with IC50 values in range 5.3 ± 0.9 to 7.5 ± 0.6 μg/mL. Acridine orange and ethidium bromide were used for the detection of viable, apoptotic, and necrotic cells. The early apoptotic cell death was observed by the compounds in

  实现了一种通过一锅反应构建含有磷酰胺和膦酸酯基团的功能化吡喃并吡唑的简单方法。该方法取决于6-氨基-3-甲基-1,4-二苯基-1,4-二氢吡喃并[2,3 - c ]吡唑-5-甲腈( 3 )与亚磷酸三乙酯和六乙基磷酰胺的反应，以及与二乙基磷酰胺的反应。在氯乙酰氯或二硫化碳存在下的亚磷酸酯。对产品的抗微生物、抗氧化和抗增殖特性进行了筛选。化合物7显示出有希望的抗菌和抗氧化特性。此外，化合物8 显示出对 MCF-7、HepG-2 和 HCT-116 癌细胞的有效细胞毒性作用，IC 50值范围为 5.3 ± 0.9 至 7.5 ± 0.6 μg/mL 。吖啶橙和溴化乙锭用于检测活细胞、凋亡细胞和坏死细胞。在所有类型的处理细胞中均观察到化合物的早期凋亡细胞死亡。化合物5、7和8对所有处理过的细胞诱导高百分比的坏死。在 HepG-2 细胞中用化合物3处理后，晚期细胞凋亡被记录为高比率。
• A convenient one-pot synthesis of novel functionalized thiophene, thieno[2,3-<i>b</i>] thiophene, thiopyran, and thiopyrano[2,3-<i>b</i>]thiopyran bearing phosphonate groups
  作者：Tarik E. Ali、Mohammed A. Assiri

  DOI：10.1080/17415993.2021.1909027

  日期：2021.9.3

  ABSTRACT Design of some novel functionalized thiophene, thieno[2,3-b]thiophene, thiopyran and thiopyrano[2,3-b]thiopyran bearing phosphonate groups was described in one-pot through simple two steps. The methodology depended on the reaction of three-component of chloroacetyl chloride with triethyl phosphite in the presence of sodium 2,2-dicyanoethene-1,1-bis(thiolate) or sodium (2,2-dicyano-1-methy

  摘要 一些新型官能化噻吩、噻吩并[2,3- b ]噻吩、噻喃和含有膦酸酯基团的噻喃并[2,3- b ]噻喃的设计通过简单的两步在一锅法中进行了描述。该方法取决于氯乙酰氯的三组分与亚磷酸三乙酯在 2,2-二氰基乙烯-1,1-双（硫醇）钠或 (2,2-二氰基-1-甲硫基乙烯-1- yl)thiolate 以一定的顺序。
• Reactions of Nitrosovinylphosphonates with Electron-Rich Alkenes and Heterocycles
  作者：Emanuel Guimarães、Américo Lemos、Marta Lopes

  DOI：10.1080/10426500701407425

  日期：2007.7.19

  In the presence of a base, chlorohydroxyiminophosphonates are converted in situ into the corresponding transient nitrosovinylphosphonates, which react as heterodienes with electron-rich alkenes and heterocycles producing oxazines and open-chain oximes in moderate yields and good selectivity. This approach may be regarded as a new strategy for the synthesis of precursors of α-amino phosphonic acids

  在碱的存在下，氯羟基亚氨基膦酸酯被原位转化为相应的瞬态亚硝基膦酸酯，其作为杂二烯与富电子烯烃和杂环反应，以中等产率和良好的选择性产生恶嗪和开链肟。该方法可被视为合成α-氨基膦酸前体的一种新策略。