(d,l)-2-ethoxy-1-eicosyloxyphosphoryl dichloride | 104602-75-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (d,l)-2-ethoxy-1-eicosyloxyphosphoryl dichloride
• 英文别名: 1-Dichlorophosphoryloxy-2-ethoxyicosane
• CAS: 104602-75-7
• 化学式: C₂₂H₄₅Cl₂O₃P
• 分子量: 459.477
• InChiKey: HJECDIGPQKBUQT-UHFFFAOYSA-N

物化性质

• 沸点：
  508.7±33.0 °C(Predicted)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  28
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  甲苯磺酸胆碱 、 (d,l)-2-ethoxy-1-eicosyloxyphosphoryl dichloride 在 吡啶 、 水 作用下， 生成 rac-(2-ethoxyeicos-1-yl)phosphocholine
  参考文献：
  名称：

  Antitumor activity of (2-alkoxyalkyl)- and (2-alkoxyalkenyl)phosphocolines

  摘要：

  Analogues of the synthetic antitumor phospholipid ALP (1-octadecyl-2-methyl-sn-glycero-3-phosphocholine; alkyl lysophospholipid) in which the 1-ether oxygen atom has been removed have been prepared and evaluated for in vitro and in vivo anticancer activity. Compounds are presented in which the saturated long chain varies in length from 8 to 25 carbon atoms. Sites of unsaturation are also incorporated into the framework in some examples. In particular, rac-(2-ethoxyeicosyl)phosphocholine (10) displays the best in vivo activity of the chemical series against a variety of transplanted tumors and activates murine peritoneal macrophages to express tumor cytotoxicity in vitro. However, 10 does not offer the wide spectrum of antitumor activity we feel necessary to warrant further study.

  DOI：

  10.1021/jm00162a009
• 作为产物：
  描述：

  2-ethoxy-1-eicosanol 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 0.58h， 生成 (d,l)-2-ethoxy-1-eicosyloxyphosphoryl dichloride
  参考文献：
  名称：

  Antitumor activity of (2-alkoxyalkyl)- and (2-alkoxyalkenyl)phosphocolines

  摘要：

  Analogues of the synthetic antitumor phospholipid ALP (1-octadecyl-2-methyl-sn-glycero-3-phosphocholine; alkyl lysophospholipid) in which the 1-ether oxygen atom has been removed have been prepared and evaluated for in vitro and in vivo anticancer activity. Compounds are presented in which the saturated long chain varies in length from 8 to 25 carbon atoms. Sites of unsaturation are also incorporated into the framework in some examples. In particular, rac-(2-ethoxyeicosyl)phosphocholine (10) displays the best in vivo activity of the chemical series against a variety of transplanted tumors and activates murine peritoneal macrophages to express tumor cytotoxicity in vitro. However, 10 does not offer the wide spectrum of antitumor activity we feel necessary to warrant further study.

  DOI：

  10.1021/jm00162a009

文献信息

• 2-alkoxy-1-alkoxy phosphoryl dichlorides
  申请人：Eli Lilly and Company

  公开号：US04659859A1

  公开（公告）日：1987-04-21

  2-Alkoxy C.sub.12-26 straight-chain alkyl hydroxyphosphoryl cholines, useful as hypotensive agents, anti-cancer agents and as anti-inflammatory agents.

  2-烷氧基C.sub.12-26直链烷基羟基磷酰胆碱，可用作降压剂、抗癌剂和抗炎剂。
• BONJOUKLIAN, ROSANNE;PHILLIPS, MICHAEL L.
  作者：BONJOUKLIAN, ROSANNE、PHILLIPS, MICHAEL L.

  DOI：——

  日期：——
• US4659859A
  申请人：——

  公开号：US4659859A

  公开（公告）日：1987-04-21
• Antitumor activity of (2-alkoxyalkyl)- and (2-alkoxyalkenyl)phosphocolines
  作者：Rosanne Bonjouklian、Michael L. Phillips、Kathy M. Kuhler、Gerlad B. Grindey、Gerald A. Poore、Richard M. Schultz、Marilyn G. Altom

  DOI：10.1021/jm00162a009

  日期：1986.12

  Analogues of the synthetic antitumor phospholipid ALP (1-octadecyl-2-methyl-sn-glycero-3-phosphocholine; alkyl lysophospholipid) in which the 1-ether oxygen atom has been removed have been prepared and evaluated for in vitro and in vivo anticancer activity. Compounds are presented in which the saturated long chain varies in length from 8 to 25 carbon atoms. Sites of unsaturation are also incorporated into the framework in some examples. In particular, rac-(2-ethoxyeicosyl)phosphocholine (10) displays the best in vivo activity of the chemical series against a variety of transplanted tumors and activates murine peritoneal macrophages to express tumor cytotoxicity in vitro. However, 10 does not offer the wide spectrum of antitumor activity we feel necessary to warrant further study.