(2S,9Z)-2-(tert-butoxycarbonylamino)octadec-9-enoic acid | 434938-03-1

• 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: (2S,9Z)-2-(tert-butoxycarbonylamino)octadec-9-enoic acid
• 英文别名: 2S-(tert-butoxycarbonylamino)-oleic acid；(2s,9z)-2-(t-Butoxycarbonylamino)-octadec-9-enoic acid；(Z,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]octadec-9-enoic acid
• CAS: 434938-03-1
• 化学式: C₂₃H₄₃NO₄
• 分子量: 397.599
• InChiKey: YXJGSNREBAWYKG-CBUFDYBVSA-N

物化性质

• 沸点：
  505.3±43.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,9Z)-2-(tert-butoxycarbonylamino)octadec-9-enoic acid 在 N-甲基吗啉 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and In vivo anti-inflammatory activity of long-chain 2-amino-alcohols

  摘要：

  The synthesis of optically pure long-chain 2-amino-alcohols and 1-O-dodecyl-2-deoxy-2-amino-sn-glyceroI was carried out starting from L- or D-Boc-Ser(OBn)-ol by oxidation and consecutive Wittig reaction or etherification reaction. 2-Amino-oleyl alcohol was synthesized by reduction of the corresponding 2-amino-oleic acid. All the long chain amino-alcohols presented interesting inhibition of carrageenin-induced paw edema in rats (ED50 from 0.017 to 0.010 mmol/kg). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00939-3
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (S)-α-aminooleic acid 在 三乙胺 作用下， 以 甲醇 为溶剂， 以98%的产率得到(2S,9Z)-2-(tert-butoxycarbonylamino)octadec-9-enoic acid
  参考文献：
  名称：

  Synthesis and In vivo anti-inflammatory activity of long-chain 2-amino-alcohols

  摘要：

  The synthesis of optically pure long-chain 2-amino-alcohols and 1-O-dodecyl-2-deoxy-2-amino-sn-glyceroI was carried out starting from L- or D-Boc-Ser(OBn)-ol by oxidation and consecutive Wittig reaction or etherification reaction. 2-Amino-oleyl alcohol was synthesized by reduction of the corresponding 2-amino-oleic acid. All the long chain amino-alcohols presented interesting inhibition of carrageenin-induced paw edema in rats (ED50 from 0.017 to 0.010 mmol/kg). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00939-3

文献信息

• A novel monoacylglycerol lipase inhibitor with analgesic and anti-inflammatory activity
  作者：Victoria Magrioti、George Naxakis、Dimitra Hadjipavlou-Litina、Alexandros Makriyannis、George Kokotos

  DOI：10.1016/j.bmcl.2008.09.039

  日期：2008.10

  A variety of long chain 1,2-diamines and related compounds were synthesized and tested for their activity on fatty acid amide hydrolase (FAAH) and monoacyglycerol lipase (MGL). (2S,9Z)-Octadec-9-ene-1,2-diamine selectively inhibits MGL (K-i 21.8 mu M) without significantly affecting FAAH. This compound exhibited interesting in vivo analgesic and anti-inflammatory properties, suggesting that selective inhibitors of MGL may be valuable novel agents for the treatment of inflammatory pain. (C) 2008 Elsevier Ltd. All rights reserved.
• Triacylglycerols Based on 2-(<i>N</i>-<i>tert</i>-Butoxycarbonylamino)oleic Acid Are Potent Inhibitors of Pancreatic Lipase
  作者：Victoria Magrioti、Robert Verger、Violetta Constantinou-Kokotou

  DOI：10.1021/jm034202s

  日期：2004.1.1

  A novel class of potent human pancreatic lipase (HPL) inhibitors was developed. Triacylglycerol analogues containing 2-(N-tert-butoxycarbonylamino) fatty acids were synthesized, and their ability to form stable films at the air/ water interface was studied. The inhibition of human digestive lipases by the compounds synthesized was studied by the monolayer technique, and the triesters of glycerol and 2-methylglycerol with 2-(N-tert-butoxycarbonylamino)oleic acid were found to be potent inhibitors of HPL.