[5-(Diethoxy-phosphorylmethyl)-naphthalen-1-ylmethyl]-phosphonic acid diethyl ester | 25075-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [5-(Diethoxy-phosphorylmethyl)-naphthalen-1-ylmethyl]-phosphonic acid diethyl ester
• 英文别名: 1,5-Bis(diethoxyphosphorylmethyl)naphthalene；1,5-bis(diethoxyphosphorylmethyl)naphthalene
• CAS: 25075-80-3
• 化学式: C₂₀H₃₀O₆P₂
• 分子量: 428.402
• InChiKey: JCEFMSKIBCNULG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  [5-(Diethoxy-phosphorylmethyl)-naphthalen-1-ylmethyl]-phosphonic acid diethyl ester 在 盐酸 、 水 作用下， 生成 naphthalene-1,5-bis(methylphosphonic) acid adduct with morpholine (1:2)
  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：

  1,5-二甲基萘 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 [5-(Diethoxy-phosphorylmethyl)-naphthalen-1-ylmethyl]-phosphonic acid diethyl ester
  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

• Synthesis of benzylic mono(α,α-difluoromethylphosphonates) and benzylic bis(α,α-difluoromethylphosphonates) via electrophilic fluorination
  作者：Scott D. Taylor、A.Nicole Dinaut、Avinash N. Thadani、Zheng Huang

  DOI：10.1016/0040-4039(96)01847-3

  日期：1996.11

  A series of benzylic mono(α,α-difluoromethylphosphonates) and benzylic bis(α,α-difluoromethylphosphonates) have been prepared via electrophilic fluorination of the corresponding benzylic phosphonates.

  通过相应的苄基膦酸酯的亲电氟化，制备了一系列苄基单（α，α-二氟甲基膦酸酯）和苄基双（α，α-二氟甲基膦酸酯）。
• US4009193A
  申请人：——

  公开号：US4009193A

  公开（公告）日：1977-02-22
• 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.