(9H-Xanthen-9-yl)-phosphonic acid diethyl ester | 81642-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (9H-Xanthen-9-yl)-phosphonic acid diethyl ester
• 英文别名: diethyl (9H-xanthen-9-yl)phosphonate；diethyl 9H-xanthen-9-ylphosphonate
• CAS: 81642-99-1
• 化学式: C₁₇H₁₉O₄P
• 分子量: 318.309
• InChiKey: SJNXFABGJMVTOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (9H-Xanthen-9-yl)-phosphonic acid diethyl ester 生成 Xanthen-9-yl-phosphonsaeure
  参考文献：
  名称：

  Benzylphosphonic acid inhibitors of human prostatic acid phosphatase

  摘要：

  A series of alpha-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme which has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 mu M), and alpha-(2-phenylethyl)benzylphosphonic acid (14 mu M) The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through alpha-carbon substitution.

  DOI：

  10.1016/0960-894x(96)00018-2
• 作为产物：
  描述：

  氧杂蒽 、 亚磷酸二乙酯 以 乙腈 为溶剂， 反应 6.0h， 以12%的产率得到(9H-Xanthen-9-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Exogenous-oxidant-free electrochemical oxidative C–H phosphonylation with hydrogen evolution

  摘要：

  我们在此报告一种通用且环境友好的电化学氧化C-H磷酰化协议。

  DOI：

  10.1039/c9cc00975b

文献信息

• Electrochemically dehydrogenative C–H/P–H cross-coupling: effective synthesis of phosphonated quinoxalin-2(1<i>H</i>)-ones and xanthenes
  作者：Ke-Jing Li、Yang-Ye Jiang、Kun Xu、Cheng-Chu Zeng、Bao-Guo Sun

  DOI：10.1039/c9gc01474h

  日期：——

  phosphonation of quinoxalin-2(1H)-ones and C(sp3)–H phosphonation of xanthenes has been developed. The chemistry was performed in an undivided cell under constant current conditions and features a wide range of substrates, up to 99% yield and it is free of transition-metal catalysts- and external oxidants, thereby providing a straightforward approach for dehydrogenative C–H/P–H cross-coupling. In addition

  已开发出一种有效的电化学方法，用于喹喔啉-2（1 H）-酮的C（sp 2）-H磷酸化和x吨的C（sp 3）-H磷酸化。该化学反应是在恒定电流条件下在一个未分开的电池中进行的，具有多种底物，产率高达99％，并且不含过渡金属催化剂和外部氧化剂，从而为CH / H /脱氢提供了直接的方法P–H交叉耦合。另外，对照实验表明，某些反应可能涉及自由基途径。
• Visible light irradiated photocatalytic C(sp³)–H phosphorylation of xanthenes and 9,10-dihydroacridines with P(O)–H compounds
  作者：Mingjun Liu、Jiarui Zhu、Xuming Jiang、Xiangyun Yang、Qian Chen

  DOI：10.1039/d3ob01053h

  日期：——

  Photocatalytic C(sp3)–H phosphorylation of xanthenes and 9,10-dihydroacridines with P(O)–H compounds under the irradiation of 18 W blue LEDs at room temperature using fluorescein as the photocatalyst and molecular oxygen (O2) as the sole oxidant has been achieved. The newly developed reaction provides direct access to 9-phosphorylated xanthene derivatives with good functional group compatibility.

  以荧光素为光催化剂，分子氧 (O 2 ) 为光催化剂，室温下 18 W 蓝光 LED 照射下，氧杂蒽和 9,10-二氢吖啶与 P(O)-H 化合物的光催化 C(sp 3 )–H磷酸化已实现唯一氧化剂。新开发的反应可以直接获得具有良好官能团相容性的9-磷酸化呫吨衍生物。