diethyl (1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthalenyl)phosphonate | 184347-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: diethyl (1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthalenyl)phosphonate
• 英文别名: 2-diethoxyphosphoryl-7-methoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 184347-10-2
• 化学式: C₁₅H₂₁O₅P
• 分子量: 312.303
• InChiKey: YCSFHSICMMEMED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthalenyl)phosphonate 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 7-methoxyspiro[3,4-dihydro-1H-naphthalene-2,1'-cyclopropane]-1-ol
  参考文献：
  名称：

  Structure−Activity Relationship Studies on the 5-HT_1A Receptor Affinity of 1-Phenyl-4-[ω-(α- or β-tetralinyl)alkyl]piperazines. 4

  摘要：

  The synthesis of 1-phenylpiperazines, linked in the alpha or beta position of the tetralin moiety on the terminal part of the N-4 alkyl chain, and their radioligand binding affinities for 5-HT1A, 5-HT2A, D-1, D-2, alpha(1), and alpha(2) receptors along with SAR studies on the 5-HT1A receptor are reported. Several changes have been carried out on previous structures of type 2, by inserting the alkyl chain with variable length in the alpha or beta position of the tetralin moiety and by changing the position of the methoxy group on the aromatic ring of the tetralin nucleus. The highest affinity (IC50 = 0.50 nM) and selectivity for the 5-HT1A receptor were showed by 1-phenylpiperazine 2a with a three-membered alkyl chain bearing a 5-methoxytetralin-1-yl ring in the omega position.

  DOI：

  10.1021/jm9604538
• 作为产物：
  描述：

  7-甲氧基-1-萘满酮 、 氯磷酸二乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.58h， 以65%的产率得到diethyl (1,2,3,4-tetrahydro-7-methoxy-1-oxo-2-naphthalenyl)phosphonate
  参考文献：
  名称：

  Togni试剂亲电三氟甲基化合成α-三氟甲基-β-酮膦酸酯

  摘要：

  摘要 利用 Togni 试剂亲电三氟甲基化开发了一种合成三氟甲基膦酸酯的新方法。各种 β-酮膦酸酯以中等至良好的产率转化为相应的 α-三氟甲基-β-酮膦酸酯。该协议还可以扩展到其他氟烷基化反应，如五氟乙基化。图形概要

  DOI：

  10.1080/00397911.2016.1139724

文献信息

• Synthesis of 1,3-Aminoalcohols and Spirocyclic Azetidines via Tandem Hydroxymethylation and Aminomethylation Reaction of β-Keto Phosphonates with <i>N</i>-Nosyl-<i>O</i>-(2-bromoethyl)hydroxylamine
  作者：Binyu Wu、Hongbing Chen、Min Gao、Xiangnan Gong、Lin Hu

  DOI：10.1021/acs.orglett.1c01091

  日期：2021.6.4

  α-aminomethylation reaction of aromatic cyclic β-keto phosphonates with N-nosyl-O-(2-bromoethyl)hydroxylamine in the presence of DBU base has been developed, affording a range of 1,3-aminoalcohols in good yields. The resultant products could be flexibly transformed into the spirocyclic and bispirocyclic azetidines via one step of Mitsunobu reaction. Mechanistic study revealed that hydroxylamine in situ generated

  在 DBU 碱存在下，芳香环 β-酮膦酸酯与N - nosyl - O-（2-溴乙基）羟胺的前所未有的串联 α-羟甲基化和 α-氨基甲基化反应被开发出来，得到了一系列 1,3-氨基醇收益良好。所得产物可以通过Mitsunobu反应一步灵活地转化为螺环和双螺环氮杂环丁烷。机理研究表明，羟胺原位生成甲醛和诺磺酰胺，进而引发连续的 Horner-Wadsworth-Emmons、Michael 和 aldol 反应。
• Synthesis of <font>α</font>-trifluoromethyl-<font>β</font>-keto phosphonates by electrophilic trifluoromethylation with Togni reagent
  作者：Wen-Zhi Fu、Yangen Huang、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1080/00397911.2016.1139724

  日期：2016.3.3

  method of trifluoromethylated phosphonates was developed via electrophilic trifluoromethylation with Togni reagent. A variety of β-keto phosphonates were converted into the corresponding α-trifluoromethyl-β-keto phosphonates in moderate to good yields. This protocol could also be extended to other fluoroalkylation reactions, such as pentafluoroethylation. GRAPHICAL ABSTRACT

  摘要 利用 Togni 试剂亲电三氟甲基化开发了一种合成三氟甲基膦酸酯的新方法。各种 β-酮膦酸酯以中等至良好的产率转化为相应的 α-三氟甲基-β-酮膦酸酯。该协议还可以扩展到其他氟烷基化反应，如五氟乙基化。图形概要
• Structure−Activity Relationship Studies on the 5-HT_1A Receptor Affinity of 1-Phenyl-4-[ω-(α- or β-tetralinyl)alkyl]piperazines. 4
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Marcello Leopoldo、Vincenzo Tortorella、Maria Gioia Fornaretto、Carla Caccia、Robert A. McArthur

  DOI：10.1021/jm9604538

  日期：1996.1.1

  The synthesis of 1-phenylpiperazines, linked in the alpha or beta position of the tetralin moiety on the terminal part of the N-4 alkyl chain, and their radioligand binding affinities for 5-HT1A, 5-HT2A, D-1, D-2, alpha(1), and alpha(2) receptors along with SAR studies on the 5-HT1A receptor are reported. Several changes have been carried out on previous structures of type 2, by inserting the alkyl chain with variable length in the alpha or beta position of the tetralin moiety and by changing the position of the methoxy group on the aromatic ring of the tetralin nucleus. The highest affinity (IC50 = 0.50 nM) and selectivity for the 5-HT1A receptor were showed by 1-phenylpiperazine 2a with a three-membered alkyl chain bearing a 5-methoxytetralin-1-yl ring in the omega position.