bis(2-chloroethyl) (2-bromo-2-nitroethenyl)phosphonate

• 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) (2-bromo-2-nitroethenyl)phosphonate
• 英文别名: bis(2-chloroethyl) 2-bromo-2-nitroethenylphosphonate；bis(2-chloroethyl)-2-bromo-2-nitroethenylphosphonate；bis(2-chloroethyl) 2-bromo-2-nitroethenephosphonate；Bis(2-chloroethyl)-2-bromo-2-nitroethenyl-phosphonate；(Z)-2-[bis(2-chloroethoxy)phosphoryl]-1-bromo-1-nitroethene
• 化学式: C₆H₉BrCl₂NO₅P
• 分子量: 356.925
• InChiKey: APNOLERCCQWGGJ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 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) (2-bromo-2-nitroethenyl)phosphonate 在 三乙胺 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 bis(2-chloroethyl) (4,5-dimethyl-2-nitrocyclohexa-1,4-dien-1-yl)phosphonate
  参考文献：
  名称：

  Synthesis and structure of phosphorylated nitrocyclohexenes

  摘要：

  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.

  DOI：

  10.1134/s1070363207010045
• 作为产物：
  描述：

  O,O-bis(2-chloroethyl) 1,2-dibromo-2-nitroethenylphosphonate 以78%的产率得到
  参考文献：
  名称：

  Botata Zh. E., Deiiko L. I., Kostina T. K., Baranow G. M., Berestowichkaj+, Zh. obshh. khimii, 65 (1995) N 1, S 160

  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。
• 2-Nitro-and 2-bromo-2-nitroethylphosphonates in the reaction with sodium azide
  作者：N. A. Anisimova、N. G. Makarova、G. A. Berkova、V. M. Berestovitskaya

  DOI：10.1134/s1070363206100069

  日期：2006.10

  The reactions of phosphorylated 2-nitro- and 2-bromo-2-nitroethenes with sodium azide involve 1,3-dipolar cycloaddition to form triazoles, aziridines and isomeric vinyl azides. The latter products were isolated as a mixture of structural isomers. The structure of the obtained compounds was determined by IR and H-1 and P-31 NMR spectroscopy.
• ——
  作者：A. A. Kuzhaeva

  DOI：10.1023/a:1023360322616

  日期：——