tetramethyl (dibromomethylene)bisphosphonate | 121151-57-3

• 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: tetramethyl (dibromomethylene)bisphosphonate
• 英文别名: tetramethyl dibromomethanediphosphonate；Dibromo-bis(dimethoxyphosphoryl)methane
• CAS: 121151-57-3
• 化学式: C₅H₁₂Br₂O₆P₂
• 分子量: 389.902
• InChiKey: ZPKDXJDASZIIQY-UHFFFAOYSA-N

物化性质

• 沸点：
  321.4±42.0 °C(Predicted)
• 密度：
  1.845±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tetramethyl (dibromomethylene)bisphosphonate 在 tin(ll) chloride 作用下， 以70%的产率得到tetramethyl (bromomethylene)bisphosphonate
  参考文献：
  名称：

  Bisphosphonic compounds. Part 3. Preparation and identification of tetraalkyl methylene- and (α-halomethylene)bisphosphonates by mass spectrometry, NMR spectroscopy and X-ray crystallography

  摘要：

  The preparation and identification of tetraalkyl methylenebisphosphonates {XYC[P(O)(OR)2]2; X = Y = H, Cl or Br and R = alkyl} have been studied. Detailed procedures are given for the synthesis of XYC[P(O)(OR)2]2 (X = Y = H; R = hexyl; X = Y = Cl or Br and R = Me). H-1, C-13 and P-31 NMR data are reported including 1J(CH), 2J(CP), 3J(CP) and 2J(PP) coupling constants. The fragmentation of 19 XYC[P(O)(OR)2]2 has been studied in the gas phase. The solid state structures are given for two compounds (X = Y = Cl, R = Pr(i) and X = Y = Br, R = Me).

  DOI：

  10.1039/p29920000835
• 作为产物：
  描述：

  四甲基亚甲基二磷酸酯 在 sodium hydroxide 、 溴 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到tetramethyl (dibromomethylene)bisphosphonate
  参考文献：
  名称：

  Bisphosphonic compounds. Part 3. Preparation and identification of tetraalkyl methylene- and (α-halomethylene)bisphosphonates by mass spectrometry, NMR spectroscopy and X-ray crystallography

  摘要：

  The preparation and identification of tetraalkyl methylenebisphosphonates {XYC[P(O)(OR)2]2; X = Y = H, Cl or Br and R = alkyl} have been studied. Detailed procedures are given for the synthesis of XYC[P(O)(OR)2]2 (X = Y = H; R = hexyl; X = Y = Cl or Br and R = Me). H-1, C-13 and P-31 NMR data are reported including 1J(CH), 2J(CP), 3J(CP) and 2J(PP) coupling constants. The fragmentation of 19 XYC[P(O)(OR)2]2 has been studied in the gas phase. The solid state structures are given for two compounds (X = Y = Cl, R = Pr(i) and X = Y = Br, R = Me).

  DOI：

  10.1039/p29920000835

文献信息

• An improved synthetic method and the first crystal structures for (dihalomethylene)bisphosphonate partial esters
  作者：Jouko J. Vepsäläinen、Jussi Kivikoski、Markku Ahlgrén、Heikki E. Nupponen、Esko K. Pohjala

  DOI：10.1016/0040-4020(95)00314-x

  日期：1995.6

  A new general and selective strategy for the synthesis of (dihalomethylene)bisphosphonic acid (XYMBP) partial alkyl esters (PE) with high selectivity and purity has been developed. Preparation is started from selected XYMBP tetraesters using tertiary or secondary amines as dealkylating reagents leading to trialkyl or P,P′-dialkyl XYMBP PEs, respectively. The solid state structures are given for three

  已开发出一种新的具有选择性和高纯度的合成（二卤代亚甲基）双膦酸（XYMBP）偏烷基酯（PE）的新的通用和选择性策略。使用叔胺或仲胺作为脱烷基剂，从选定的XYMBP四酯开始制备，分别生成三烷基或P，P'-二烷基XYMBP PE。给出了以下三种化合物的固态结构：Cl 2 C [P（O）（OPr i）（O - Na +）] [P（O）（O - Na +）2 ]和Cl 2 C [P （O）（OPr i）（O − X +）] 2，其中X = Na +或H2 Ñ +（CH 2 CH 2）2 O.
• Bisphosphonate-Generated ATP-Analogs Inhibit Cell Signaling Pathways
  作者：Satish R. Malwal、Bing O’Dowd、Xinxin Feng、Petri Turhanen、Christopher Shin、Jiaqi Yao、Boo Kyung Kim、Noman Baig、Tianhui Zhou、Sandhya Bansal、Rahul L. Khade、Yong Zhang、Eric Oldfield

  DOI：10.1021/jacs.8b02363

  日期：2018.6.20

  adenine nucleotide translocase. Inhibition of the latter is due to formation in cells of analogs of ATP: the isopentenyl ester of ATP (ApppI) or an AppXp-type analog of ATP, such as AMP-clodronate (AppCCl2p). We screened both ApppI as well as AppCCl2p against a panel of 369 kinases finding potent inhibition of some tyrosine kinases by AppCCl2p, attributable to formation of a strong hydrogen bond between

  双膦酸盐是一类主要用于治疗骨质疏松症、佩吉特病和癌症的药物。已经提出它们通过抑制一种或多种靶标起作用，包括蛋白质异戊二烯化、表皮生长因子受体或腺嘌呤核苷酸移位酶。后者的抑制是由于 ATP 类似物在细胞中的形成：ATP 的异戊烯酯 (ApppI) 或 ATP 的 AppXp 型类似物，例如 AMP-氯膦酸盐 (AppCCl2p)。我们针对一组 369 种激酶筛选了 ApppI 和 AppCCl2p，发现 AppCCl2p 能有效抑制某些酪氨酸激酶，这归因于酪氨酸和末端膦酸酯之间形成强氢键。然后我们合成了在细胞中转化为其他 ATP 类似物的双膦酸盐前体药物，发现了抑制细胞信号通路的低 nM 激酶抑制剂。
• Bisphosphonic compounds VIII. A facile and selective one-pot synthesis of P,P-dialkyl (dichloromethylene)bisphosphonate partial esters
  作者：Jouko Vepsäläinen、Heikki Nupponen、Esko Pohjala

  DOI：10.1016/0040-4039(96)00605-3

  日期：1996.5

  The preparations of P,P-dialkyl partial esters of (dichloromethylene)bisphosphonic acid from readily available tetraesters with good selectivity and purity have been developed.

  已经开发了由容易获得的具有良好的选择性和纯度的四酯制备（二氯亚甲基）双膦酸的P，P-二烷基偏酯的方法。
• McKenna, Charles E.; Khawli, Leslie A.; Ahmad, Wan-Yaacob, Phosphorus and Sulfur and the Related Elements, 1988, vol. 37, p. 1 - 12
  作者：McKenna, Charles E.、Khawli, Leslie A.、Ahmad, Wan-Yaacob、Pham, Phuong、Bongartz, Jean-Pierre

  DOI：——

  日期：——
• MCKENNA, CHARLES E.;KHAWLI, LESLIE A.;AHMAD, WAN YAACOB;PHAM, PHUONG;BONG+, PHOSPHORUS AND SULFUR., 37,(1988) N-2, C. 1-12
  作者：MCKENNA, CHARLES E.、KHAWLI, LESLIE A.、AHMAD, WAN YAACOB、PHAM, PHUONG、BONG+

  DOI：——

  日期：——