(Z)-1-(1,1-dimethylethoxy)-10-nonadecen-2-ol | 104532-28-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-1-(1,1-dimethylethoxy)-10-nonadecen-2-ol
• 英文别名: (Z)-(+/-)-1-t-butoxy-10-nonadecen-2-ol；(Z)-1-[(2-methylpropan-2-yl)oxy]nonadec-10-en-2-ol
• CAS: 104532-28-7
• 化学式: C₂₃H₄₆O₂
• 分子量: 354.617
• InChiKey: NJHRUCZIMNCTLG-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-(1,1-dimethylethoxy)-10-nonadecen-2-ol 在 吡啶 、 水 、 三氯化铁 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 9.83h， 生成 rac-(Z)-(2-ethoxy-10-nonadecen-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：

  (Z)-十八碳-9-烯醛 、 甲基叔丁基醚 在 potassium tert-butylate 、 仲丁基锂 、 lithium bromide 作用下， 生成 (Z)-1-(1,1-dimethylethoxy)-10-nonadecen-2-ol
  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

• US4647685A
  申请人：——

  公开号：US4647685A

  公开（公告）日：1987-03-03
• 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.