3-butyl-1-ethoxy-4-iodobenzo[c][1,2]oxaphosphinine 1-oxide | 682348-81-8

• 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: 3-butyl-1-ethoxy-4-iodobenzo[c][1,2]oxaphosphinine 1-oxide
• 英文别名: 3-Butyl-1-ethoxy-4-iodo-2,1lambda5-benzoxaphosphinine 1-oxide；3-butyl-1-ethoxy-4-iodo-2,1λ5-benzoxaphosphinine 1-oxide
• CAS: 682348-81-8
• 化学式: C₁₄H₁₈IO₃P
• 分子量: 392.173
• InChiKey: WAZGSEUEDHDIFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  3-butyl-1-ethoxy-4-iodobenzo[c][1,2]oxaphosphinine 1-oxide 在 bis-triphenylphosphine-palladium(II) chloride 甲酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3-butyl-1-ethoxybenzo[c][1,2]oxaphosphinine 1-oxide
  参考文献：
  名称：

  Synthesis of Phosphaisocoumarins via Iodocyclization

  摘要：

  4-lodophosphaisocoumarins can be prepared in good yield and with high regioselectivity under mild conditions by the reaction of o-(1-alkynyl)phenylphosphonates with I-2 or ICI. The present reaction represents the first example of a phosphonate iodocyclization onto a C-C triple bond. The resulting iodides can be further elaborated using palladium-catalyzed coupling reactions.

  DOI：

  10.1021/ol0499506
• 作为产物：
  描述：

  2-(diethoxyphosphonyl)phenyl 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy)ethanesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 碘 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3-butyl-1-ethoxy-4-iodobenzo[c][1,2]oxaphosphinine 1-oxide
  参考文献：
  名称：

  Synthesis of Phosphaisocoumarins via Iodocyclization

  摘要：

  4-lodophosphaisocoumarins can be prepared in good yield and with high regioselectivity under mild conditions by the reaction of o-(1-alkynyl)phenylphosphonates with I-2 or ICI. The present reaction represents the first example of a phosphonate iodocyclization onto a C-C triple bond. The resulting iodides can be further elaborated using palladium-catalyzed coupling reactions.

  DOI：

  10.1021/ol0499506

文献信息

• Synthesis of 4-halophosphaisocoumarins via halocyclization of 2-(1-alkynyl)phenylphosphonates
  作者：Ai-Yun Peng、Yi-Xiang Ding

  DOI：10.1016/j.tet.2005.08.032

  日期：2005.10

  A series of 4-halophosphaisocoumarins were prepared with high regioselectivity in good to excellent yields under mild conditions by the reaction of 2-(1-alkynyl)phenylphosphonic acid diesters with I2 in CHCl3 or ICl in CH2Cl2, or by the reaction of 2-(1-alkynyl)phenylphosphonic acid monoesters with NBS or NCS in DMF. Whether the alkynylphosphonates could cyclize or not was affected by the substituents

  通过2-（1-炔基）苯基膦酸二酯与I 2在CHCl 3中或ICl在CH 2 Cl 2中的反应，或通过在2-（1-炔基）苯基膦酸单酯与NBS或NCS在DMF中的反应 炔基膦酸酯是否可以环化受取代基，反应溶剂和亲电试剂的影响。讨论了这种反应的原理。
• Phosphaisocoumarins as a new class of potent inhibitors for pancreatic cholesterol esterase
  作者：Baojian Li、Binhua Zhou、Hailiang Lu、Lin Ma、Ai-Yun Peng

  DOI：10.1016/j.ejmech.2010.01.038

  日期：2010.5

  Due to the importance of pancreatic cholesterol esterase (CEase) as a potential target in atherosclerosis and for the development of hypocholesterolemic agents, there are increasing interests in designing and synthesizing CEase inhibitors. In the present study, we prepared forty-five isocoumarin phosphorus analogues (i.e., phosphaisocoumarins) and investigated the inhibition of these compounds on the CEase. The results showed that some phosphaisocoumarins could act as potent inhibitors of CEase. The most potent inhibitors, compounds 9d, 10a and 12e give IC(50) values of 4.8 mu M, 2.3 mu M and 1.9 mu M, respectively. The inhibition mechanism and kinetic characterization studies indicate that they are reversible competitive inhibitors. (C) 2010 Published by Elsevier Masson SAS.
• Synthesis of Phosphaisocoumarins via Iodocyclization
  作者：Ai-Yun Peng、Yi-Xiang Ding

  DOI：10.1021/ol0499506

  日期：2004.4.1

  4-lodophosphaisocoumarins can be prepared in good yield and with high regioselectivity under mild conditions by the reaction of o-(1-alkynyl)phenylphosphonates with I-2 or ICI. The present reaction represents the first example of a phosphonate iodocyclization onto a C-C triple bond. The resulting iodides can be further elaborated using palladium-catalyzed coupling reactions.