methyl [2',2'-2H2]-undec-10-enoate | 1019641-48-5

• 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: methyl [2',2'-2H2]-undec-10-enoate
• 英文别名: methyl [2',2'-²H₂]-undec-10-enoate
• CAS: 1019641-48-5
• 化学式: C₁₂H₂₂O₂
• 分子量: 200.29
• InChiKey: KISVAASFGZJBCY-ZWGOZCLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  14.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl [2',2'-2H2]-undec-10-enoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 [2',2'-2H2]-undec-10-en-1-ol
  参考文献：
  名称：

  Bolalipid Membrane Structure Revealed by Solid-State ²H NMR Spectroscopy

  摘要：

  Membranes made from three specifically deuterium-labeled ether-linked bolalipids, [1',1',20',20'-H-2(4)[C(20)BAS-PC, [2',2',19',19'-H-2(4)]C(20)BAS-PC, or [10',11'-H-2(2)]C(20)BAS-PC, were analyzed by H-2 NMR spectroscopy. Unlike more common monopolar, ester-linked phospholipids, C(20)BAS-PC exhibits a high degree of orientational order throughout the membrane and the sn-1 chain of the lipid initially penetrates the bilayer at an orientation different from that of the bilayer normal, resulting in inequivalent deuterium atoms at the C1 position. The approximate hydrophobic layer thickness and area per lipid are 18.4 A and 60.4 A(2), respectively, at 25 degrees C, and their respective thermal expansion coefficients are within 20% of the monopolar phospholipid, DLPC.

  DOI：

  10.1021/ja710190p
• 作为产物：
  描述：

  10-烯酸甲酯 在 sodium t-butanolate 作用下， 以72%的产率得到methyl [2',2'-2H2]-undec-10-enoate
  参考文献：
  名称：

  Bolalipid Membrane Structure Revealed by Solid-State ²H NMR Spectroscopy

  摘要：

  Membranes made from three specifically deuterium-labeled ether-linked bolalipids, [1',1',20',20'-H-2(4)[C(20)BAS-PC, [2',2',19',19'-H-2(4)]C(20)BAS-PC, or [10',11'-H-2(2)]C(20)BAS-PC, were analyzed by H-2 NMR spectroscopy. Unlike more common monopolar, ester-linked phospholipids, C(20)BAS-PC exhibits a high degree of orientational order throughout the membrane and the sn-1 chain of the lipid initially penetrates the bilayer at an orientation different from that of the bilayer normal, resulting in inequivalent deuterium atoms at the C1 position. The approximate hydrophobic layer thickness and area per lipid are 18.4 A and 60.4 A(2), respectively, at 25 degrees C, and their respective thermal expansion coefficients are within 20% of the monopolar phospholipid, DLPC.

  DOI：

  10.1021/ja710190p