O,O-dicyclopentylphosphoroamidate

• 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: O,O-dicyclopentylphosphoroamidate
• 英文别名: Dicyclopentyl Phosphoramidate；[amino(cyclopentyloxy)phosphoryl]oxycyclopentane
• 化学式: C₁₀H₂₀NO₃P
• 分子量: 233.247
• InChiKey: BDYGAPLPLXNVSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  环戊醇 在 氨 、 三氯化磷 作用下， 以 吡啶 、 四氯化碳 、 乙醚 、 xylene 为溶剂， 生成 O,O-dicyclopentylphosphoroamidate
  参考文献：
  名称：

  Binding of a Designed Substrate Analogue to Diisopropyl Fluorophosphatase:  Implications for the Phosphotriesterase Mechanism

  摘要：

  A wide range of organophosphorus nerve agents, including Soman, Sarin, and Tabun is efficiently hydrolyzed by the phosphotriesterase enzyme diisopropyl fluorophosphatase (DFPase) from Loligo vulgaris. To date, the lack of available inhibitors of DFPase has limited studies on its mechanism. The de novo design, synthesis, and characterization of substrate analogues acting as competitive inhibitors of DFPase are reported. The 1.73 A crystal structure of O,O-dicyclopentylphosphoroamidate (DcPPA) bound to DFPase shows a direct coordination of the phosphoryl oxygen by the catalytic calcium ion. The binding mode of this substrate analogue suggests a crucial role for electrostatics in the orientation of the ligand in the active site. This interpretation is further supported by the crystal structures of double mutants D229N/N120D and D229N/N175D, designed to reorient the electrostatic environment around the catalytic calcium. The structures show no differences in their calcium coordinating environment, although they are enzymatically inactive. Additional double mutants E21Q/N120D and E21Q/N175D are also inactive. On the basis of these crystal structures and kinetic and mutagenesis data as well as isotope labeling we propose a new mechanism for DFPase activity. Calcium coordinating residue D229, in concert with direct substrate activation by the metal ion, renders the phosphorus atom of the substrate susceptible for attack of water, through generation of a phosphoenzyme intermediate. Our proposed mechanism may be applicable to the structurally related enzyme paraoxonase (PON), a component of high-density lipoprotein (HDL).

  DOI：

  10.1021/ja061887n

文献信息

• IMIDIC ACID COMPOUND HAVING DIVALENT ANION AND PROCESS FOR PRODUCING THE SAME
  申请人：Central Glass Co., Ltd.

  公开号：EP3222624A1

  公开（公告）日：2017-09-27

  Provided is a novel imidic acid compound having a divalent anion useful as a pharmaceutical intermediate, an agrochemical intermediate, an acid catalyst, a battery electrolyte or an antistatic agent. The imidic acid compound is a divalent imidic acid compound represented by the following general formula (1) or (2). [In formulae (1) and (2), R1 to R3 represent a fluorine atom or an organic groups selected from a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkoxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, and wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group. M1 and M2 represent protons, metal cations or onium cations.]

  本文提供了一种具有二价阴离子的新型亚胺酸化合物，可用作医药中间体、农用化学品中间体、酸催化剂、电池电解液或抗静电剂。该亚胺酸化合物是由以下通式（1）或（2）表示的二价亚胺酸化合物。 [在式(1)和(2)中，R1 至 R3 代表一个氟原子或一个有机基团，该有机基团选自直链或支链 C1-10 烷氧基、C2-10 烯氧基、C2-10 烷炔氧基、C3-10 环烷氧基、C3-10 环烯氧基和 C6-10 芳氧基，其中有机基团中还可能存在一个氟原子、一个氧原子或一个不饱和键。M1和M2代表质子、金属阳离子或鎓阳离子]。
• Imidic acid compound having divalent anion and process for producing the same
  申请人：CENTRAL GLASS CO., LTD.

  公开号：US10287165B2

  公开（公告）日：2019-05-14

  Provided is a novel imidic acid compound having a divalent anion useful as a pharmaceutical intermediate, an agrochemical intermediate, an acid catalyst, a battery electrolyte or an antistatic agent. The imidic acid compound is a divalent imidic acid compound represented by the following general formula (1) or (2). [In formulae (1) and (2), R1 to R3 represent a fluorine atom or an organic groups selected from a linear or branched C1-10 alkoxy group, a C2-10 alkenyloxy group, a C2-10 alkynyloxy group, a C3-10 cycloalkoxy group, a C3-10 cycloalkenyloxy group and a C6-10 aryloxy group, and wherein a fluorine atom, an oxygen atom or an unsaturated bond may also be present in the organic group. M1 and M2 represent protons, metal cations or onium cations.]

  本文提供了一种具有二价阴离子的新型亚胺酸化合物，可用作医药中间体、农用化学品中间体、酸催化剂、电池电解液或抗静电剂。该亚胺酸化合物是由以下通式（1）或（2）表示的二价亚胺酸化合物。 [在式 (1) 和 (2) 中，R1 至 R3 代表氟原子或有机基团，这些有机基团选自直链或支链 C1-10 烷氧基、C2-10 烯氧基、C2-10 烷炔氧基、C3-10 环烷氧基、C3-10 环烯氧基和 C6-10 芳氧基，其中有机基团中还可能存在氟原子、氧原子或不饱和键。M1和M2代表质子、金属阳离子或鎓阳离子]。