(3E,5E,9E)-12-Cyano-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-8-phenylselanyl-dodeca-3,5,9-trienoic acid tert-butyl ester | 479092-41-6

• 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,5E,9E)-12-Cyano-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-8-phenylselanyl-dodeca-3,5,9-trienoic acid tert-butyl ester
• CAS: 479092-41-6
• 化学式: C₂₇H₃₃NO₃Se
• 分子量: 498.524
• InChiKey: FMFMLLBQKGUILM-IZGVGOKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3E,5E,9E)-12-Cyano-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-8-phenylselanyl-dodeca-3,5,9-trienoic acid tert-butyl ester 在 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (3E,5E,9E)-12-Cyano-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-8-phenylselanyl-dodeca-3,5,9-trienoic acid methyl ester
  参考文献：
  名称：

  The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule

  摘要：

  The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a beta-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01290-5
• 作为产物：
  描述：

  N,N-diethylbenzeneselenamide 在 正丁基锂 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 (3E,5E,9E)-12-Cyano-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-8-phenylselanyl-dodeca-3,5,9-trienoic acid tert-butyl ester
  参考文献：
  名称：

  The diastereoselective asymmetric total synthesis of NG-391, a neuronal cell-protecting molecule

  摘要：

  The stereocontrolled total synthesis of (+)-NG-391, a neuronal cell-protecting molecule, is described along with the determination of its absolute stereochemistry. The following reactions in this synthesis are particularly noteworthy: (1) The stereoselective construction of the conjugated (E,E,E,E,E)-pentaene from an (E,E,E)-alcohol using an IBX oxidation followed by stereoselective Horner-Emmons reaction. (2) The (E)-selective Knoevenagel condensation of a beta-ketonitrile with a chiral 2-alkoxyaldehyde prepared from (S)-malic acid. (3) A diastereoselective epoxidation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01290-5