diethyl hept-6-en-1-ylphosphonate | 141917-82-0

• 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: diethyl hept-6-en-1-ylphosphonate
• 英文别名: diethyl 6-heptenylphosphonate；7-Diethoxyphosphorylhept-1-ene
• CAS: 141917-82-0
• 化学式: C₁₁H₂₃O₃P
• 分子量: 234.276
• InChiKey: QPHIIIYGMBDKCL-UHFFFAOYSA-N

物化性质

• 沸点：
  308.1±21.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  diethyl hept-6-en-1-ylphosphonate 在 盐酸 、 硼烷 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-(Chloromethoxy)-6-diethoxyphosphorylhexane
  参考文献：
  名称：

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]嘧啶（8-氮杂鸟嘌呤）膦酸酯无环衍生物是嘌呤核苷磷酸化酶的抑制剂。

  摘要：

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]-嘧啶（8-氮杂鸟嘌呤）的膦酸酯无环衍生物是嘌呤核苷磷酸化酶（PNPase）的抑制剂，其Ki'值范围为0.05至1.6 microM。这些化合物是有效的PNPase抑制剂无环鸟苷二磷酸的酶稳定同类物（53）。

  DOI：

  10.1021/jm950736k
• 作为产物：
  描述：

  7-溴-1-庚烯 、 亚磷酸三乙酯 反应 16.0h， 以71%的产率得到diethyl hept-6-en-1-ylphosphonate
  参考文献：
  名称：

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]嘧啶（8-氮杂鸟嘌呤）膦酸酯无环衍生物是嘌呤核苷磷酸化酶的抑制剂。

  摘要：

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]-嘧啶（8-氮杂鸟嘌呤）的膦酸酯无环衍生物是嘌呤核苷磷酸化酶（PNPase）的抑制剂，其Ki'值范围为0.05至1.6 microM。这些化合物是有效的PNPase抑制剂无环鸟苷二磷酸的酶稳定同类物（53）。

  DOI：

  10.1021/jm950736k

文献信息

• Copper-Catalyzed Radical Aminotrifluoromethylation of Alkenes
  作者：Haiwen Xiao、Haigen Shen、Lin Zhu、Chaozhong Li

  DOI：10.1021/jacs.9b06141

  日期：2019.7.24

  We report herein an unprecedented protocol for aminotrifluoromethylation of alkenes. With Cu(OTf)2 as the catalyst, the reaction of alkenes, (bpy)Zn(CF3)2 and N-fluorobis(benzenesulfonyl)imide (NFSI) at room temperature provides the corresponding aminotrifluoromethylation products in satisfactory yields with high regioselectivity opposite to those driven by CF3 radical addition. The method exhibits

  我们在此报告了一种前所未有的烯烃氨基三氟甲基化方案。以 Cu(OTf)2 作为催化剂，烯烃、(bpy)Zn(CF3)2 和 N-氟双（苯磺酰基）酰亚胺（NFSI）在室温下反应以令人满意的收率提供相应的氨基三氟甲基化产物，与那些由 CF3 自由基加成驱动的。该方法表现出广泛的底物范围和广泛的官能团兼容性。提出了一种机制，涉及到烯烃的 N-自由基加成，然后是烷基自由基的三氟甲基化。
• Cobalt-Catalyzed Markovnikov-Selective Radical Hydroacylation of Unactivated Alkenes with Acylphosphonates
  作者：Benxiang Zhang、Jiayan He、Yi Li、Tao Song、Yewen Fang、Chaozhong Li

  DOI：10.1021/jacs.1c02629

  日期：2021.4.7

  Acylphosphonates having the 5,5-dimethyl-1,3,2-dioxophosphinanyl skeleton are developed as efficient intermolecular radical acylation reagents, which enable the cobalt-catalyzed Markovnikov hydroacylation of unactivated alkenes at room temperature under mild conditions. The protocol exhibits broad substrate scope and wide functional group compatibility, providing branched ketones in satisfactory yields

  具有5,5-二甲基-1,3,2-二氧代次膦烷基骨架的酰基膦酸酯被开发为有效的分子间自由基酰化试剂，其能够在温和的条件下在室温下对未活化的烯烃进行钴催化的马尔可夫尼可夫加氢酰化。该方案具有广泛的底物范围和广泛的官能团兼容性，可提供令人满意的收率的支链酮。提出了一种涉及Co-H介导的氢原子转移和随后被酰基膦酸酯捕获烷基的机理。
• Heterocyclic compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0478292A1

  公开（公告）日：1992-04-01

  Compounds of the formula (I): or a pharmaceutically acceptable salt or ester thereof, wherein X¹, is nitrogen or a group CH and X² is nitrogen or a group CR⁵ wherein R⁵ is hydrogen, hydroxy, halo or a group NHR⁶ wherein R⁶ is hydrogen or a C₁₋₄ alkyl or C₁₋₄ alkylcarbonyl group, R¹ is amino or hydrogen; R² is hydrogen, halo, SH, a group NHR⁷ wherein R⁷ is hydrogen or a C₁₋₄ alkyl or C₁₋₄ alkylcarbonyl group or R² is a group OR⁸ wherein R⁸ is hydrogen, C₁₋₄ alkyl or benzyl, R³ and R⁴ are the same or different and each is hydrogen or halo, X³ is a chain containing m CH₂ groups and n oxygen atoms, m being 1, 2, 3, 4, or 5 and n being 0, 1 or 2 the sum of m and n being 2, 3, 4, 5, or 6; are disclosed as inhibitors of the enzyme, purine nucleoside phosphorylase, pharmaceutical compositions containing the compounds, their use in medicine and processes for their preparation are also described.

  式(I)的化合物或其医药上可接受的盐或酯，其中X¹为氮或CH基团，X²为氮或CR⁵基团，其中R⁵为氢、羟基、卤素或NHR⁶基团，其中R⁶为氢或C₁₋₄烷基或C₁₋₄烷基羰基基团，R¹为氨基或氢；R²为氢、卤素、SH、NHR⁷基团，其中R⁷为氢或C₁₋₄烷基或C₁₋₄烷基羰基基团，或R²为OR⁸基团，其中R⁸为氢、C₁₋₄烷基或苄基，R³和R⁴相同或不同，均为氢或卤素，X³为含有m个CH₂基团和n个氧原子的链，其中m为1、2、3、4或5，n为0、1或2，m和n的总和为2、3、4、5或6；作为嘌呤核苷酸磷酸化酶的抑制剂进行了披露，还描述了含有该化合物的制药组合物、它们在医学上的用途以及其制备方法。
• [[(Guaninylalkyl)phosphinico]methyl]phosphonic Acids. Multisubstrate Analog Inhibitors of Human Erythrocyte Purine Nucleoside Phosphorylase
  作者：James L. Kelley、Ed W. McLean、Ronald C. Crouch、Devron R. Averett、Joel V. Tuttle

  DOI：10.1021/jm00006a020

  日期：1995.3

  A series of [[(guaninylalkyl)phosphinico]methyl]phosphonic acids, 2, was synthesized and tested as inhibitors of human erythrocyte purine nucleoside phosphorylase (PNPase). The target (phosphinicomethyl)phosphonic acids 2 were synthesized in six or seven steps from alkenylphosphonates 4. The latter were converted to the intermediate alkylmesylates 9 in a series of steps that included (1) conversion of the diethyl phosphonates 4 to the (phosphinoylmethyl)pho sphonates 7 and (2) conversion of the terminal double bond of [(alkenylphosphinoyl)methyl]-phosphonates 7 to the alkylmesylates 9. The pure 9-isomers 2 were obtained by alkylation of 2-amino-6-(2-methoxyethoxy)-9H-purine with alkylmesylates 9 followed by hydrolysis of the protecting groups with concentrated hydrochloric acid and ion exchange chromatography to give 2 as hydrated ammonium salts. The most potent inhibitor of human erythrocyte PNPase, [[[5-(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)pentyl]phosphinico]methyl]phosphonic acid(2b), was a multisubstrate analogue inhibitor with a K-i' of 3.1 nM. Optimum PNPase inhibitory activity required the presence of zinc ions in the assay medium. These potent inhibitors of PNPase exhibited only weak activity against human leukemic T-cells in vitro.
• Guanine, Pyrazolo[3,4-<i>d</i>]pyrimidine, and Triazolo[4,5-<i>d</i>]pyrimidine (8-Azaguanine) Phosphonate Acyclic Derivatives as Inhibitors of Purine Nucleoside Phosphorylase
  作者：Lilia M. Beauchamp、Joel V. Tuttle、Martha E. Rodriguez、Marcos L. Sznaidman

  DOI：10.1021/jm950736k

  日期：1996.1.1

  Phosphonate acyclic derivates of guanines, pyrazolo[3,4-d]pyrimidines, and triazolo[4,5-d]-pyrimidines (8-azaguanines) are inhibitors of the enzyme purine nucleoside phosphorylase (PNPase) with Ki' values ranging from 0.05 to 1.6 microM. These compounds are enzymatically stable congeners of the potent PNPase inhibitor acyclovir diphosphate (53).

  鸟嘌呤，吡唑并[3,4-d]嘧啶和三唑并[4,5-d]-嘧啶（8-氮杂鸟嘌呤）的膦酸酯无环衍生物是嘌呤核苷磷酸化酶（PNPase）的抑制剂，其Ki'值范围为0.05至1.6 microM。这些化合物是有效的PNPase抑制剂无环鸟苷二磷酸的酶稳定同类物（53）。