bis(2-chloroethyl)-β-nitroethenylphosphonate | 114246-14-9

• 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: bis(2-chloroethyl)-β-nitroethenylphosphonate
• 英文别名: bis(2-chloroethyl) (2-nitroethenyl)phosphonate；bis(2-chloroethyl) 2-nitroethenylphosphonate；bis(2-chloroethyl)-2-nitroethenylphosphonate；bis(2-chloroethyl) 2-nitroethenephosphonate；bis(2-chloroethyl) 2-nitrovinylphosphonate；Bis(2-chloroethyl)-b-nitroethenylphosphonate；1-chloro-2-[2-chloroethoxy-[(E)-2-nitroethenyl]phosphoryl]oxyethane
• CAS: 114246-14-9
• 化学式: C₆H₁₀Cl₂NO₅P
• 分子量: 278.029
• InChiKey: SHAMAGRSWYNYHN-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(2-chloroethyl)-β-nitroethenylphosphonate 在 氯 作用下， 以 溶剂黄146 为溶剂， 反应 192.0h， 生成 bis(2-chloroethyl) 2-chloro-2-nitrovinylphosphonate
  参考文献：
  名称：

  Patsanovskii; Ishmaeva; Berestovitskaya, Russian Journal of General Chemistry, 1998, vol. 68, # 3, p. 384 - 389

  摘要：

  DOI：
• 作为产物：
  描述：

  1-[双(2-氯乙氧基)磷酰基]-2-硝基乙醇 在 硫酸 、 sodium carbonate 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 bis(2-chloroethyl)-β-nitroethenylphosphonate
  参考文献：
  名称：

  Baranov, G. M.; Perekalin, V. V., Journal of general chemistry of the USSR, 1987, vol. 57, p. 699 - 704

  摘要：

  DOI：

文献信息

• Reactions of 2-Nitro- and 2-Bromo-2-nitroethenylphosphonates with Anthracene
  作者：N. A. Anisimova、A. A. Kuzhaeva、G. A. Berkova、L. I. Deiko、V. M. Berestovitskaya

  DOI：10.1007/s11176-005-0299-6

  日期：2005.5

  Bis(2-chloroethyl) 2-nitro- and 2-bromo-2-nitroethenylphosphonates react with anthracene along two competing pathways: [4+2] cycloaddition and electrophilic substitution; in the case of the bromo derivative, the resulting products undergo dehydrobromination under the reaction conditions to form anthracene- and dihydroanthracene-containing nitroethenylphosphonates.

  2-硝基和 2-溴-2-硝基乙烯基膦酸双(2-氯乙基)酯与蒽通过两种竞争途径发生反应：[4+2] 环加成和亲电取代；在溴衍生物的情况下，生成物在反应条件下发生脱氢溴化反应，生成含蒽和二氢蒽的硝基乙烯基膦酸盐。
• Specific Features of the Reaction of 2-Nitro- and 2-Bromo-2-Nitroethenylphosphonates with Furan
  作者：N. A. Anisimova、A. A. Kuzhaeva、G. A. Berkova、V. M. Berestovitskaya、L. I. Deiko

  DOI：10.1007/s11176-005-0504-7

  日期：2005.11

  Investigation of the reactions of phosphorylated 2-nitro- and 2-bromo-2-nitroethenes with furan showed that bis(2-chloroethyl) 2-nitroethenylphosphonate reacts with this heterocycle according to the pathway of diene condensation, while in the case of 2-bromo-2-nitroethenylphosphonate by two pathways, the complete diene synthesis accompanied by aromatization, and the electrophilic substitution at C2-atom of the furan with the subsequent partial dehydrohalogenation.

  对磷酸化的 2-硝基和 2-溴-2-硝基乙烯与呋喃反应的研究表明，2-硝基乙烯基膦酸双(2-氯乙基)酯与这种杂环的反应途径是二烯缩合，而 2-溴-2-硝基乙烯基膦酸双(2-氯乙基)酯的反应途径则有两种，一种是完全二烯合成并伴随芳香化，另一种是在呋喃的 C2 原子上发生亲电取代，随后部分脱氢卤化。
• Reaction of (2-Nitro- and 2-Bromo-2-nitroethenyl)phosphonates with 1,3-Cyclohexadiene
  作者：N. A. Anisimova、A. A. Kuzhaeva、G. A. Berkova、L. I. Deiko、V. M. Berestovitskaya

  DOI：10.1007/s11176-005-0365-0

  日期：2005.7

  Specific features of the reactions of bis(chloroethyl) 2-nitro- and 2-bromo-2-nitroethenylphosphonates with 1,3-cyclohexadiene were studied. It was found that the reaction with 2-nitroethenylphosphonate occurs stereoselectively and provides bis(2-chloroethyl) endo-(3-nitrobicyclo[2.2.2]oct-5-en-2-yl)phosphonate. 2-Bromo-2-nitroethenylphosphonate under the same conditions gives a mixture of the endo and exo isomers of the corresponding nitrobicyclooctenes. Enhanced tendency of adducts derived from gem-bromonitroethenyl-phosphonates for intramolecular transformations, such as dehydrohalogenation and aromatization, under the cycloaddition conditions was revealed.

  研究了 2-硝基和 2-溴-2-硝基乙烯基膦酸双(氯乙基)酯与 1,3-环己二烯反应的具体特征。研究发现，与 2-硝基乙烯基膦酸盐的反应是立体选择性的，反应生成了双(2-氯乙基)内(3-硝基二环[2.2.2]辛-5-烯-2-基)膦酸盐。在相同条件下，2-溴-2-硝基乙烯基膦酸盐可生成相应的硝基双环辛烯内、外异构体的混合物。研究发现，在环加成条件下，由溴硝基乙烯基膦酸盐衍生的加合物发生分子内转化（如脱氢卤化和芳香化）的趋势增强。
• Synthesis of Indolylnitroethylphosphonates and Indolylnitronitropropanoates
  作者：Z. M. Sarkisyan、S. V. Makarenko、V. M. Berestovitskaya、L. I. Deiko、G. A. Berkova

  DOI：10.1023/b:rugc.0000007671.40282.1a

  日期：2003.8

  compounds is an actual problem of modern organic chemistry. From this point of view of undeniable interest is indole nitroethylation reactions leading to functionally substituted nitro precursors of triptamine that forms the basis of garmine alkaloids (garmine, garmane, and brevicarine) and such widely used drugs as indopan, arifon, cavinton, and diazoline [1 3]. Up to now reactions of indole and some of its

  在对天然化合物进行修饰的基础上，设计新的生物活性化合物，包括药物，是现代有机化学的一个现实问题。从这个不可否认的角度来看，吲哚硝基乙基化反应导致曲普胺的功能取代硝基前体形成了garmine生物碱（garmine，garmane和brevicarine）和广泛使用的药物如indopan，arifon，cavinton和diazoline [ 1 3]。迄今为止，吲哚及其一些衍生物与 2-烷基-（芳基，杂基）-1-硝基乙烯 [4 11]、偕二硝基苯乙烯 [12] 和双（2-氯乙基）（2-溴-2）的反应-nitroethenyl)phosphonate [13] 已被研究。然而，这些反应最常需要较长时间和相对严格的条件才能发生（在 80 100 C 下加热、使用催化剂、
• Synthesis and structure of phosphorylated nitrocyclohexenes
  作者：V. M. Berestovitskaya、N. A. Anisimova、A. A. Kuzhaeva、G. A. Berkova、L. I. Deiko

  DOI：10.1134/s1070363207010045

  日期：2007.1

  Diene condensations of 2-nitro- and 2-bromo-2-nitroethenylphosplionates with 2,3-dimethyl-1,3-butadiene, as well as with 2,4-dihydro- and 3-methyl-2,4-dihydrothiophene 1,1-dioxides that generate 1,3-butadiene and isoprene under the reaction conditions were effected. (6-Nitrocyclohex-3-en-1-yl)phosphonates and their dehydrogenation and/or dehydrohalogenation products, namely nitrocyclohexadienyl- and nitrophenyl-phosphonates were prepared. The structure of the obtained compounds was proved by IR and H-1 and P-31 NMR spectroscopy, and independent synthesis.