dimethyl phosphorobromidate | 24167-74-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: dimethyl phosphorobromidate
• 英文别名: dimethyl phosphoryl bromide；phosphorobromidic acid dimethyl ester；bromophosphoric acid dimethyl ester；Bromophosphorsaeure-dimethylester；Dimethyl-bromophosphat；dimethylbromophosphate；Dimethyl bromophosphate；[bromo(methoxy)phosphoryl]oxymethane
• CAS: 24167-74-6
• 化学式: C₂H₆BrO₃P
• 分子量: 188.946
• InChiKey: UBDQVSSPNXWQNH-UHFFFAOYSA-N

物化性质

• 沸点：
  45-47 °C(Press: 0.8 Torr)
• 密度：
  1.692±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dimethyl phosphorobromidate 、 benzyl N-(4-amino-2-methoxy-phenyl)carbamate 在 吡啶 作用下， 以41%的产率得到dimethyl N-<4-<(benzyloxy)carboxamido>-3-methoxyphenyl>phosphoramidate
  参考文献：
  名称：

  Potential antitumor agents. 37. Organophosphorus derivatives of 9-anilinoacridine

  摘要：

  A series of 9-anilinoacridine derivatives substituted in the anilino ring with a variety of phosphoramide and related substitutents has been prepared, and the antitumor activity has been evaluated both in vivo and in vitro against the L1210 or P-388 mouse leukemia systems. The DNA-binding properties were measured using the ethidium displacement method, and the structural requirements for strong binding were found to differ from those for antileukemic activity. For high biological activity a marked preference for oxygen-containing substituents on the phosphorus atom was noted, while for high DNA binding a requirement for nitrogen-containing or cyclized substituents was observed. The most active congeners, as assayed in both in vitro and in vivo systems, were comparable in activity to the clinically utilized anilinoacridine derivative N-[4'-(9-acridinylamino)-3'-methoxyphenyl]methanesulfonamide (m-AMSA, amsacrine).

  DOI：

  10.1021/jm00352a027
• 作为产物：
  描述：

  亚磷酸氢二甲酯 在 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 作用下， 生成 dimethyl phosphorobromidate
  参考文献：
  名称：

  Goldwhite; Saunders, Journal of the Chemical Society, 1955, p. 3564

  摘要：

  DOI：

文献信息

• Synthesis and properties of 4-(dibromomethyl)benzenecarbaldehyde
  作者：Mukattis B. Gazizov、Svetlana Yu. Ivanova、Liliya R. Bagauva、Rafail A. Khairullin、Rashid Z. Musin

  DOI：10.1016/j.tetlet.2015.12.005

  日期：2016.1

  for the first time using a new method which also allowed the co-preparation of terephthalic aldehyde. The reaction of this aldehyde with primary amines resulted in the formation of imines, including those containing an additional acetal group, while the reaction with trialkyl orthoformates led to the formation of acetals. The latter compounds were transformed into 4-(dibromomethyl)-substituted benzenes

  使用新方法首次合成了4-（二溴甲基）苯甲醛，该方法还可以共同制备对苯二醛。该醛与伯胺的反应导致形成亚胺，包括含有额外缩醛基的亚胺，而与原甲酸三烷基酯的反应则导致缩醛的形成。通过与三氯化磷和P（III）酸的酯的连续反应，将后一种化合物转化为在侧链中具有磷官能团的4-（二溴甲基）-取代的苯。
• Potential antitumor agents. 52. Carbamate analogs of amsacrine with in vivo activity against multidrug-resistant P388 leukemia
  作者：Gordon W. Rewcastle、Bruce C. Baguley、Graham J. Atwell、William A. Denny

  DOI：10.1021/jm00392a009

  日期：1987.9

  provided increased activity against the multidrug-resistant P388/ADR leukemia subline in vivo. Since activity against such resistant tumors is of great clinical significance, a series of acridine-substituted carbamate derivatives were evaluated against both wild-type and ADR/resistant P388 leukemia and the Lewis lung solid tumor in vivo. Structure-activity relationships for all three tumor lines were similar

  对一系列与抗白血病药物氨苯磺酸有关的苯胺取代的9-苯胺基cr啶的研究表明，1'-氨基甲酸酯基团在体内对多药耐药的P388 / ADR白血病亚系提供增强的活性。由于针对这种抗药性肿瘤的活性具有重要的临床意义，因此在体内针对野生型和ADR /抗药性P388白血病以及Lewis肺实体瘤评估了一系列of啶取代的氨基甲酸酯衍生物。所有三个肿瘤细胞系的结构活性关系相似，其中3-卤代-5-甲基和3-卤代5-甲氧基化合物被证明是活性最高的。这种取代模式还提供了最高的DNA结合。此类化合物（尤其是3-氯-5-甲基和3-氯-5-甲氧基）对野生型P388和Lewis肺具有体内活性，其活性与先前开发的最佳氨水analogue类似物相当（治愈率超过50％） ，以及P388 / ADR活动。这项工作从根本上完成了amsacrine系列抗肿瘤药的开发。
• Phosphonate–Phosphinate Rearrangement
  作者：Renzhe Qian、Alexander Roller、Friedrich Hammerschmidt

  DOI：10.1021/jo502567j

  日期：2015.1.16

  benzylic position and dimethyl N-Boc α-aminophosphonates at the CH3O group to induce phosphonate–phosphinate rearrangements. In the former case, the migration of the phosphorus substituent from the nitrogen to the carbon atom followed a retentive course with some racemization because of the involvement of a benzyllithium as an intermediate.

  LiTMP金属化的由1-苯基乙胺和1,2,3,4-四氢萘-1-基胺衍生的N -Boc-磷酰胺酸二甲酯在CH 3 O基团上具有较高的选择性，从而生成短寿命的氧甲基锂。这些被异构化为非对映异构的羟甲基膦酸酯（磷酸酯-膦酸酯重排）。然而，s -BuLi优先地将衍生自1-苯基乙胺的N -Boc-氨基磷酸二甲酯N -Bocα-氨基膦酸酯转化为N -Bocα-氨基膦酸酯。仅s- BuLi在苄基位置上去质子化的羟甲基膦酸二甲基二甲酯和在CH 3上N -Bocα-氨基膦酸二甲酯的去质子化O基团诱导膦酸酯-次膦酸酯重排。在前一种情况下，由于苄基锂作为中间体的参与，磷取代基从氮向碳原子的迁移经历了保持性过程，具有一定的消旋作用。
• [EN] STRUCTURAL CAROTENOID ANALOGS FOR THE INHIBITION AND AMELIORATION OF DISEASE<br/>[FR] ANALOGUES DE CAROTENOIDES STRUCTURAUX POUR L'INHIBITION ET LA REDUCTION DE MALADIE
  申请人：HAWAII BIOTECH INC

  公开号：WO2004011423A3

  公开（公告）日：2004-05-06
• Petrow et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 1486,1489;engl.Ausg.S.1460,1462
  作者：Petrow et al.

  DOI：——

  日期：——