1,6-己烷二膦酸 | 4721-22-6

• 物质功能分类: 化学试剂 - 有机试剂
• 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
• 中文名称: 1,6-己烷二膦酸
• 中文别名: 1,6-亚己基二膦酸
• 英文名称: hexane-1,6-bisphosphonic acid
• 英文别名: 1,6-hexylenediphosphonic acid；1,2-hexylenediphosphonic acid；1,6-hexanediphosphonic acid；hexane-1,6-diyldiphosphonic acid；hexane-1,6-diylbisphosphonic acid；6-phosphonohexylphosphonic Acid
• CAS: 4721-22-6
• 化学式: C₆H₁₆O₆P₂
• mdl: MFCD01630742
• 分子量: 246.137
• InChiKey: WDYVUKGVKRZQNM-UHFFFAOYSA-N

物化性质

• 熔点：
  203.0 to 208.0 °C
• 沸点：
  533.6±60.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险等级：
  8
• 危险品运输编号：
  UN 3206
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P501,P260,P234,P264,P280,P390,P303+P361+P353,P301+P330+P331,P363,P304+P340+P310,P305+P351+P338+P310,P406,P405
• 危险性描述：
  H314,H290
• 储存条件：
  存放于惰性气体中，并避免接触湿气（尤其是防止吸湿）。

制备方法与用途

hexane-1,6-diyl diphosphonic acid是一种PROTAC连接子，属于烷基链类。它可用于合成PROTAC分子。

反应信息

• 作为反应物：
  描述：

  1,6-己烷二膦酸 、 zinc(II) acetate dihydrate 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 96.0h， 生成
  参考文献：
  名称：

  Isoreticular Investigation into the Formation of Four New Zinc Alkylbisphosphonate Families

  摘要：

  Through the systematic investigation of zinc alkylbisphosphonates, four new structural families have been obtained. These families are named zinc alkyl-tunnel, -gate, -cation, and -sheet (ZAT, ZAG, ZAC, and ZAS) for convenience and have been synthesized and further extended through isoreticular design utilizing alkylbis(phosphonic acid) ligands of the formula H2O3PCnH2nPO3H2 (n = 3-6) (H(4)Ln). Both even- and odd-length chains were utilized to help determine the effect of chain conformation on structure formation. The investigation lead to two known compounds (ZAG-4, and ZAS-3) and nine new compounds, two of which contain large 1-D channels. The crystal structures of all compounds were determined by single-crystal X-ray diffraction. Of the nine new compounds, only seven of them fall into the new families. In three of the four families, the structure is controlled by alkyl-chain length and conformation (i.e., odd vs even), and in the fourth, a conformational distortion allows both odd and even lengths to form the given structure. Isoreticular species using n = 3 and 5 were obtained in both the ZAT and the ZAS families; using n = 4 and 6 were obtained in the ZAG family; and n = 4-6, in the ZAC family.

  DOI：

  10.1021/cg500568e
• 作为产物：
  描述：

  tetraethyl hexane-1,6-diyldiphosphonate 在 盐酸 作用下， 生成 1,6-己烷二膦酸
  参考文献：
  名称：

  一些脂族二膦四氯化物

  摘要：

  制备并表征了一般类型为Cl 2 PO（CH 2）x POCl 2的二膦四氯化物，完成了x = 1-10的系列。首次注意到这些物质的熔点周期性，这种现象类似于在一系列不含磷的有机化合物中观察到的现象。

  DOI：

  10.1039/j39660000757

文献信息

• Microwave Michaelis–Becker synthesis of diethyl phosphonates, tetraethyl diphosphonates, and their total or partial dealkylation
  作者：Dalila Meziane、Julie Hardouin、Abdelhamid Elias、Erwann Guénin、Marc Lecouvey

  DOI：10.1002/hc.20561

  日期：——

  Diethyl phosphonates and tetraethyl alkyldiphosphonates were efficiently and rapidly prepared via the Michaelis–Becker reaction, under microwave irradiation. These compounds were then hydrolyzed to phosphonic and diphosphonic acids or selectively monodealkylated to give monoesters of phosphonic acids and symmetrical diethyl esters of diphosphonic acids. These reactions were also achieved rapidly in

  在微波辐射下，通过 Michaelis-Becker 反应高效快速地制备了膦酸二乙酯和烷基二膦酸四乙酯。然后将这些化合物水解成膦酸和二膦酸或选择性单脱烷基化得到膦酸单酯和对称二膦酸二乙酯。使用微波方法，这些反应也以令人满意的产率快速实现。该方法成功地应用于聚合物树脂的官能化。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:369–377, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20561
• Chain length effect in the functionalization of polyoxometalates with α,ω-alkyldiphosphonates
  作者：Zhiwei Liu、Wei Wang、Jinkui Tang、Weiqi Li、Weiye Yin、Xikui Fang

  DOI：10.1039/c9cc02854d

  日期：——

  group (e.g.L6vs.L5), can steer the self-assembly processes into different paths. Even homologous hybrids of L5 and L4 have seen the spin ground states switch from S = 0 to S = 9 upon shortening the chain length (L5vs.L4).

  改变在polyoxotungstates和长链α，ω-alkyldiphosphonates（的杂交复合物的有机隔离物大号Ñ由单个CH），2组（例如， L6与L5），可以引导自组装处理成不同的路径。即使是L5和L4的同源杂种，在缩短链长（L5对L4）时，自旋基态也从S = 0切换到S = 9 。
• A detailed comparative structural study of the hydrogen bonded networks in solids, obtained by the reaction of 4,4′-bipyridine and varied alkane-α,ω-diphosphonic acids
  作者：M. van Megen、W. Frank、G. J. Reiss

  DOI：10.1039/c5ce02156a

  日期：——

  In a comparative structural study, the solid state structures of seven new compounds obtained by the reaction of 4,4′-bipyridine and alkane-α,ω-diphosphonic acids with different chain lengths have been characterised by single crystal X-ray diffraction and vibrational spectroscopy. The compounds are composed of either [4,4′-Hbipy]+ or [4,4′-H2bipy]2+ cations and [H2O3P(CH2)nPO3H]− anions and exhibit

  在一项比较结构研究中，通过单晶X射线衍射和振动表征了通过不同链长的4,4'-联吡啶与烷烃-α，ω-二膦酸反应获得的七个新化合物的固态结构。光谱学。这些化合物由[4,4'-Hbipy] +或[4,4'-H 2 bipy] 2+阳离子和[H 2 O 3 P（CH 2）n PO 3 H] -阴离子组成，并呈层状具有明显分开的阴离子和阳离子区域的结构。在三[4,4'- Hbipy] +盐中，4,4'-联吡啶-1-鎓阳离子通过中等强度的，带电荷的N + -H⋯N氢键与相邻的阳离子相连，形成无限链。这些化合物的阴离子亚结构完全不同。五个[4,4'-H 2 bipy] 2+盐的晶体结构由阴离子的​​氢键合链组成，它们通过4,4'-联吡啶-1,1'-diium阳离子与相邻的链相连。除了一个以外，其他所有类型都可以分解为两种不同类型的结构，其中阳离子与阴离子链成一直线（类型1）或垂直于前述阴离子（类型2）。对于[4
• Solid state coordination chemistry: structural consequences of variations in tether length in the oxovanadium–copper–bisterpy–{O₃P(CH₂)_nPO₃}⁴⁻system, n = 1–6 (bisterpy = 2,2′:4′,4″:2″,2‴-quarterpyridyl-6′,6″-di-2-pyridine)
  作者：Wayne Ouellette、Bon-Kweon Koo、Eric Burkholder、Vladimir Golub、C. J. O'Connor、Jon Zubieta

  DOI：10.1039/b401669f

  日期：——

  Hydrothermal reactions of Na3VO4, an appropriate Cu(II) source, bisterpy and an organodiphosphonate, H2O3P(CH2)nPO3H2 (n = 1–6) yielded a family of materials of the type Cu2(bisterpy)}4+/VxOyn−/O3P(CH2)nPO3}4−. This family of bimetallic oxides is characterized by an unusual structural diversity. The oxides [Cu2(bisterpy)}V2O4O3PCH2PO3H}2] (1), [Cu2(bisterpy)(H2O)}VO2O3P(CH2)3PO3}HO3P(CH2)3PO3H2}] (4) and [Cu2(bisterpy)}V2O4O3P(CH2)6PO3H}2]·2H2O (7·2H2O) are one-dimensional, while [Cu2(bisterpy)(H2O)2}V2O4O3P(CH2)2PO3}HO3P(CH2)2PO3H}2] (2), [Cu2(bisterpy)}V4O8O3P(CH2)3PO3}2]·4H2O (3·4H2O) and [Cu2(bisterpy)}V2O4(OH)2O3P(CH2)4PO3}]·4H2O (5·4H2O) are two-dimensional. The V(IV) oxide [Cu2(bisterpy)}V4O4O3P(CH2)5PO3H}4]·7.3H2O (6·7.3H2O) provides a relatively unusual example of a three-dimensional bimetallic oxide phosphonate. The structures reveal a variety of V/P/O substructures as building blocks.

  Na3VO4、适当的Cu(II)源、bisterpy和一种有机二膦酸盐H2O3P(CH2)nPO3H2（n = 1-6）在水热反应中产生了一系列材料，类型为Cu2(bisterpy)}4+/VxOyn−/O3P( )nPO3}4−。这类双金属氧化物具有不寻常的结构多样性。氧化物[Cu2(bisterpy)}V2O4O3PCH2PO3H}2] (1)、[Cu2(bisterpy)(H2O)}VO2 ( )3PO3}H ( )3PO3H2}] (4)和[Cu2(bisterpy)}V2O4 ( )6PO3}2]·2 (7·2 )是三维的，而[Cu2(bisterpy)( )2}V2O4 ( )2PO3}H ( )2PO3H}2] (2)、[Cu2(bisterpy)}V4O8 ( )3PO3}2]·4 (3·4 )和[Cu2(bisterpy)}V2O4(OH)2 ( )4PO3}]·4 (5·4 )是二维的。V(IV)氧化物[Cu2(bisterpy)}V4O4 ( )5PO3H}4]·7.3 (6·7.3 )提供了一个相对不寻常的三维双金属氧化物膦酸盐的例子。结构显示出多样的V/P/O亚结构作为构建模块。
• Structural Diversity of the Oxovanadium Organodiphosphonate System:  A Platform for the Design of Void Channels
  作者：Wayne Ouellette、Ming Hui Yu、Charles J. O'Connor、Jon Zubieta

  DOI：10.1021/ic0517422

  日期：2006.4.17

  oxovanadium diphosphonate framework in the type 4 materials [H3N(CH2)(n)NH3][V4O4(OH)2 O3P(CH)3PO3}2] x xH2O [n = 2, x = 6 (4a); n = 3, x = 3 (4b); n = 4, x = 2 (4c); n = 5, x = 1 (4d); n = 6, x = 0.5 (4e); n = 7, x = 0 (4f)] and [H3NR]y[V4O4(OH)2 O3P(CH)3PO3}2] x xH2O [R = -CH2(NH3)CH2CH3, y = 1, x = 0 (4g); R = -CH3, n = 2, x = 3 (4h); R = -CH2CH3, y = 2, x = 1 (4i); R = -CH2CH2CH3, y = 2, x = 0 (4j);

  钒源，适当的二膦酸酯配体和水在HF存在下的水热反应提供了一系列具有中性VPO网络的化合物，这些化合物是重复出现的结构基序。当O3P（CH2）（n）PO3} 4-二膦酸酯系链的长度n为2-5时，类型为[V2O2（H2O） （ ）（n）PO3}] x x 的金属氧化物杂化物，被隔离。1型氧化物表现出典型的三维（3-D）“柱状”层结构。当n增加到6-8时，会遇到2型氧化物[V2O2（ ）4 （ ）6PO3}]的二维（2-D）“成柱状”平板结构。将间隔物进一步加长至n = 9，可提供另一种3-D结构，类型3，该结构由柱状平板的缩合构成，以提供VPO双层作为网络子结构。当引入有机阳离子为阴离子VPO网络提供电荷平衡时，会观察到4-7型氧化物。对于间隔长度n = 3，在4型材料[H3N（ ）（n）NH3] [V4O4（OH）2 （CH）3 PO 3} 2]