Tetraethyl naphthalene-1,5-diphosphonate | 172412-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Tetraethyl naphthalene-1,5-diphosphonate
• 英文别名: 1,5-Bis(diethoxyphosphoryl)naphthalene
• CAS: 172412-63-4
• 化学式: C₁₈H₂₆O₆P₂
• 分子量: 400.348
• InChiKey: YFSRROWPPOTEKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  Tetraethyl naphthalene-1,5-diphosphonate 在 盐酸 、 水 作用下， 生成
  参考文献：
  名称：

  Chains, Layers, Channels, and More: Supramolecular Chemistry of Potent Diphosphonic Tectons with Tuned Flexibility. The Generation of Pseudopolymorphs, Polymorphs, and Adducts

  摘要：

  Naphthalene-1,5.-diphosphonic acid [C10H6(PO3H2)(2), H4NDP(1,5), 1] and its more flexible counter-part, naphthalene-1,5-bis(methylphosphonic) acid [C10H6(CH2PO3H2)(2), H4NDP(1C,5C), 2], have been synthesized, characterized, and used as building blocks in supramolecular assemblies with 4-(N,N-dimethylamino)pyridine (DMAP) and morpholine. The two acids generate two distinct solvatomorphs each, with and without dimethyl sulfoxide (DMSO) molecules. The two adducts of H4NDP(1,5) with DMAP (3A and 3B) reveal conformational polymorphism caused by the rotation of phosphonic groups. The two adducts of H4NDP(1C,5C) show unexpected structural diversity, generating a symmetric hydrogen bond and creating a layered structure, 4A, or a channel structure, 4B. The adducts of both acids with morpholine (5A and 5B) allow for observing the influence of the conformational flexibility of the acids on the dimensionality of a final hydrogen bond network, which is in general higher for H4NDP(1C,5C). The structural motifs and trends are analyzed in terms of the geometric criteria of these interactions. For the first time, Hirshfeld surface analysis has also been applied for the investigation of supramolecular interactions of phosphonic acids in different protonation states.

  DOI：

  10.1021/cg400859e
• 作为产物：
  描述：

  1,5-萘二胺 在 硫酸 、 sodium iodide 、 nickel dibromide 、 sodium nitrite 作用下， 生成 Tetraethyl naphthalene-1,5-diphosphonate
  参考文献：
  名称：

  Chains, Layers, Channels, and More: Supramolecular Chemistry of Potent Diphosphonic Tectons with Tuned Flexibility. The Generation of Pseudopolymorphs, Polymorphs, and Adducts

  摘要：

  Naphthalene-1,5.-diphosphonic acid [C10H6(PO3H2)(2), H4NDP(1,5), 1] and its more flexible counter-part, naphthalene-1,5-bis(methylphosphonic) acid [C10H6(CH2PO3H2)(2), H4NDP(1C,5C), 2], have been synthesized, characterized, and used as building blocks in supramolecular assemblies with 4-(N,N-dimethylamino)pyridine (DMAP) and morpholine. The two acids generate two distinct solvatomorphs each, with and without dimethyl sulfoxide (DMSO) molecules. The two adducts of H4NDP(1,5) with DMAP (3A and 3B) reveal conformational polymorphism caused by the rotation of phosphonic groups. The two adducts of H4NDP(1C,5C) show unexpected structural diversity, generating a symmetric hydrogen bond and creating a layered structure, 4A, or a channel structure, 4B. The adducts of both acids with morpholine (5A and 5B) allow for observing the influence of the conformational flexibility of the acids on the dimensionality of a final hydrogen bond network, which is in general higher for H4NDP(1C,5C). The structural motifs and trends are analyzed in terms of the geometric criteria of these interactions. For the first time, Hirshfeld surface analysis has also been applied for the investigation of supramolecular interactions of phosphonic acids in different protonation states.

  DOI：

  10.1021/cg400859e

文献信息

• Ureido derivatives of naphthalenephosphonic acids
  申请人：Pharmacia & Upjohn S.p.A.

  公开号：US05700788A1

  公开（公告）日：1997-12-23

  Subject of the present invention are new ureido derivatives of naphthalenephosphonic acids having the following formula (I) ##STR1## wherein each of m and n, which are the same, is an integer of 1 to 4; each of p and q, which are the same, is an integer of 1 to 3; and each of the R groups, which are the same, is a free or esterified phosphonic acid group; and the pharmaceutically acceptable salts thereof.

  本发明的主题是具有以下公式（I）的萘磷酸尿素衍生物，其中m和n相同，均为1到4的整数；p和q相同，均为1到3的整数；R组相同，是自由或酯化的膦酸基团；以及其药物可接受的盐。
• UREIDO DERIVATIVES OF NAPHTHALENEPHOSPHONIC ACIDS AND PROCESS FOR THEIR PREPARATION
  申请人：PHARMACIA & UPJOHN S.p.A.

  公开号：EP0696287B1

  公开（公告）日：2000-03-08
• US5700788A
  申请人：——

  公开号：US5700788A

  公开（公告）日：1997-12-23
• [EN] UREIDO DERIVATIVES OF NAPHTHALENEPHOSPHONIC ACIDS AND PROCESS FOR THEIR PREPARATION<br/>[FR] DERIVES UREIDO DES ACIDES NAPHTALENE-PHOSPHONIQUES ET LEUR PROCEDE DE PREPARATION
  申请人：——

  公开号：WO1995023806A2

  公开（公告）日：1995-09-08

  [EN] Subject of the present invention are new ureido derivatives of naphthalenephosphonic acids having formula (I), wherein each of m and n, which are the same, is an integer of 1 to 4; each of p and q, which are the same, is an integer of 1 to 3; and each of the R groups, which are the same, is a free or esterified phosphonic acid group; and the pharmaceutically acceptable salts thereof.
  [FR] L'invention se rapporte à des nouveaux dérivés des acides naphtalène-phosphoniques de la formule générale (I) ainsi qu'aux sels pharmacologiquement acceptables de ceux-ci. Dans cette formule, m et n sont semblables, chacun représentant un nombre entier compris entre 1 et 4; p et q sont semblables, chacun représentant un nombre entier compris entre 1 et 3; et les groupes R sont semblables, chacun représentant un groupe acide phosphonique libre ou estérifié.
• Chains, Layers, Channels, and More: Supramolecular Chemistry of Potent Diphosphonic Tectons with Tuned Flexibility. The Generation of Pseudopolymorphs, Polymorphs, and Adducts
  作者：Michał J. Białek、Jan K. Zaręba、Jan Janczak、Jerzy Zoń

  DOI：10.1021/cg400859e

  日期：2013.9.4

  Naphthalene-1,5.-diphosphonic acid [C10H6(PO3H2)(2), H4NDP(1,5), 1] and its more flexible counter-part, naphthalene-1,5-bis(methylphosphonic) acid [C10H6(CH2PO3H2)(2), H4NDP(1C,5C), 2], have been synthesized, characterized, and used as building blocks in supramolecular assemblies with 4-(N,N-dimethylamino)pyridine (DMAP) and morpholine. The two acids generate two distinct solvatomorphs each, with and without dimethyl sulfoxide (DMSO) molecules. The two adducts of H4NDP(1,5) with DMAP (3A and 3B) reveal conformational polymorphism caused by the rotation of phosphonic groups. The two adducts of H4NDP(1C,5C) show unexpected structural diversity, generating a symmetric hydrogen bond and creating a layered structure, 4A, or a channel structure, 4B. The adducts of both acids with morpholine (5A and 5B) allow for observing the influence of the conformational flexibility of the acids on the dimensionality of a final hydrogen bond network, which is in general higher for H4NDP(1C,5C). The structural motifs and trends are analyzed in terms of the geometric criteria of these interactions. For the first time, Hirshfeld surface analysis has also been applied for the investigation of supramolecular interactions of phosphonic acids in different protonation states.