((3E,7E)-4,8,12-Trimethyl-trideca-3,7,11-trienyl)-phosphonic acid diethyl ester | 180088-28-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ((3E,7E)-4,8,12-Trimethyl-trideca-3,7,11-trienyl)-phosphonic acid diethyl ester
• 英文别名: (6E,10E)-13-diethoxyphosphoryl-2,6,10-trimethyltrideca-2,6,10-triene
• CAS: 180088-28-2
• 化学式: C₂₀H₃₇O₃P
• 分子量: 356.486
• InChiKey: VVWOBIIWKXPIER-XHGFWWIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  ((3E,7E)-4,8,12-Trimethyl-trideca-3,7,11-trienyl)-phosphonic acid diethyl ester 在 2,3,5-三甲基吡啶 、 正丁基锂 、 三甲基溴硅烷 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [(4E,8E)-5,9,13-trimethyl-1-oxo-1-(2-phenylethylamino)tetradeca-4,8,12-trien-2-yl]phosphonic acid
  参考文献：
  名称：

  Inhibition of farnesyl protein transferase by new farnesyl phosphonate derivatives of phenylalanine

  摘要：

  New farnesyl phosphonate derivatives of phenylalanine have been prepared as inhibitors of farnesyl-protein transferase (FPT). Enzyme inhibition studies with bovine brain FPT and rat liver squalene synthase show that compound <(3a)under bar> is a new, potent and selective FPT inhibitor. Moreover, structural modifications from <(3a)under bar> have provided some useful information concerning the key structural subunits necessary for optimum and selective FPT inhibition. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00238-7
• 作为产物：
  描述：

  甲基膦酸二乙酯 、 反,反-法呢基溴 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到((3E,7E)-4,8,12-Trimethyl-trideca-3,7,11-trienyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Inhibition of farnesyl protein transferase by new farnesyl phosphonate derivatives of phenylalanine

  摘要：

  New farnesyl phosphonate derivatives of phenylalanine have been prepared as inhibitors of farnesyl-protein transferase (FPT). Enzyme inhibition studies with bovine brain FPT and rat liver squalene synthase show that compound <(3a)under bar> is a new, potent and selective FPT inhibitor. Moreover, structural modifications from <(3a)under bar> have provided some useful information concerning the key structural subunits necessary for optimum and selective FPT inhibition. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00238-7

文献信息

• Design and synthesis of non-hydrolyzable homoisoprenoid α-monofluorophosphonate inhibitors of PPAPDC family integral membrane lipid phosphatases
  作者：Thangaiah Subramanian、Hongmei Ren、Karunai Leela Subramanian、Manjula Sunkara、Fredrick O. Onono、Andrew J. Morris、H. Peter Spielmann

  DOI：10.1016/j.bmcl.2014.08.013

  日期：2014.9

  An efficient, diversity oriented synthesis of homoisoprenoid alpha-monofluorophosphonates utilizing electrophilic fluorination is presented along with their activity as inhibitors of PPAPDC2 family integral membrane lipid phosphatases. These novel phosphatase-resistant analogues of isoprenoid monophosphates are a platform for further structure-activity relationship studies and provide access to other isoprenoid family members where the phosphate ester oxygen is replaced by a alpha-monofluoromethylene moiety. (C) 2014 Elsevier Ltd. All rights reserved.