dibenzyl (chloromethyl)phosphonate | 166049-87-2

• 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: dibenzyl (chloromethyl)phosphonate
• 英文别名: [chloromethyl(phenylmethoxy)phosphoryl]oxymethylbenzene
• CAS: 166049-87-2
• 化学式: C₁₅H₁₆ClO₃P
• 分子量: 310.717
• InChiKey: YFLPIZLPODNMOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三丁基硼 、 dibenzyl (chloromethyl)phosphonate 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成
  参考文献：
  名称：

  有机磷化合物的温和合成：含磷卡宾与有机硼烷的反应。

  摘要：

  有机硼烷在温和条件下与含磷类卡宾反应生成多种功能化的有机磷化合物。在某些情况下，可以观察到与硼相连的一组选择性迁移。次膦酸酯-硼烷复合物被引入作为合成次膦酸酯的新型合成子。

  DOI：

  10.1021/ol800085u
• 作为产物：
  描述：

  膦酸,甲基-,二(苯基甲基)酯 在 正丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.05h， 以13%的产率得到dibenzyl (chloromethyl)phosphonate
  参考文献：
  名称：

  Direct α-chlorination of O,O -dialkyl chalcogenophosphonates with phosphorus oxychloride

  摘要：

  alpha -Chlorination of phosphonates, and O,O-dialkyl thio- and selenophosphonates involving the direct reaction of their lithiated anion with phosphorus oxychloride is described. The reaction gives good results where previously known methods fail. The role of the chalcogen atom, and the influence of the nature of the alkyl chain with respect to the reactivity are discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01382-x

文献信息

• First Use of Benzyl Phosphites in theMichaelis-Arbuzov Reaction synthesis of mono-, Di-, and triphosphate analogs
  作者：Mourad Saady、Luc Lebeau、Charles Mioskowski

  DOI：10.1002/hlca.19950780314

  日期：1995.5.10

  Micaelis-Arbuzov reaction. Special experimental conditions allowed preparation of a set of phosphonate analogs of mono-, di-, and triphosphate. Furthermore, regioselective monodeprotection makes these molecules useful building blocks for the synthesis of analogs of polyphosphorylated compounds of biological interest (e.g. nucleotides), after removal of all phosphonate benzyl ester groups under very

  亚甲基苄基酯用于Micaelis-Arbuzov反应。特殊的实验条件允许制备一组单磷酸，二磷酸和三磷酸的膦酸酯类似物。此外，在非常温和的条件下以高收率除去所有膦酸酯苄酯基团之后，区域选择性单脱保护使这些分子成为合成具有生物学意义的多磷酸化化合物（例如核苷酸）的类似物的有用组成部分。
• [EN] PSILOCIN DERIVATIVES AS SEROTONERGIC PSYCHEDELIC AGENTS FOR THE TREATMENT OF CNS DISORDERS<br/>[FR] DÉRIVÉS DE PSILOCINE EN TANT QU'AGENTS SÉROTONINERGIQUES SÉROTONINERGIQUES POUR LE TRAITEMENT DE TROUBLES DU SYSTÈME NERVEUX CENTRAL
  申请人：MINDSET PHARMA INC

  公开号：WO2021155470A1

  公开（公告）日：2021-08-12

  The present application relates to psilocin derivatives of Formula (I), to processes for their preparation, to compositions comprising them and to their use in activation of a serotonin receptor in a cell, as well as to treating diseases, disorders or conditions by activation of a serotonin receptor in a cell. (I)

  本申请涉及公式（I）的哌嗪酮衍生物，以及其制备方法、包含它们的组合物以及它们在细胞中激活5-羟色胺受体的使用，以及通过激活细胞中的5-羟色胺受体治疗疾病、障碍或病况。 (I)
• β-Lactams fromD-Erythrose-Derived Imines: A Convenient Synthesis of 2,3-Diamino-2,3-dideoxy-D-mannonic-Acid Derivatives
  作者：Thomas Storz、Bruno Bernet、Andrea Vasella

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2380::aid-hlca2380>3.0.co;2-p

  日期：1999.12.15

  The D-manno-configured N-anisylated beta-lactam 40, the beta-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from D-glucose in 8-10 steps, respectively None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the D-erythroses 6, 16, and 17 with the ketene: from mesyloxyacetyl chloride (20) gave the 2-mesyloxy-D-hexono-1,3-lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (> 85%) to the corresponding azides, followed by oxidative N-deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N-atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl)phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the beta-lactam amino acid 43, besides its hydrolysis product 44. Reductive N-acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2-trifluoroacetamido N-(carboxymethyl)-beta-lactam 4 (56%). Similarly, 47 gave the 2-trifluoroacetamide 48 (89%), and hence, the 2-amino-N-(phosphonoylmethyl)-beta-lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected beta-lactams 31a and 35 led to the 2,3-diamino-2,3-dideoxy-D-mannonamides 51 and 53, respectively (Scheme 6).
• Synthesis of Di- and Triphosphate Ester Analogs via a Modified Michaelis-Arbuzov Reaction
  作者：M Saady

  DOI：10.1016/00404-0399(50)10097-

  日期：1995.7.17
• New route to amino[²H₂]methylphosphonic acid via bis(trifluoroethyl) phosphonate transesterification
  作者：Sylvie Berté-Verrando、Rachel Dizière、Mohammad Samadi、Philippe Savignac

  DOI：10.1039/p19950003125

  日期：——

  Transesterification of bis(trifluoroethyl) chloromethyl- and azidomethyl-phosphonates with alcohols in the presence of catalytic quantities of alcoholates gives dialkyl chloromethyl- and azidomethyl-phosphonates in good yield. This process has been used for the synthesis of dibenzyl azido[H-2(2)]methylphosphonate which has been reduced and hydrogenolised to amino[H-2(2)]methylphosphonic acid under neutral conditions.