(2E,6E,8E)-4-Chloro-10-eth-(E)-ylidene-2,8-dimethyl-undeca-2,6,8-trienedioic acid 11-tert-butyl ester 1-methyl ester | 479092-45-0

• 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: (2E,6E,8E)-4-Chloro-10-eth-(E)-ylidene-2,8-dimethyl-undeca-2,6,8-trienedioic acid 11-tert-butyl ester 1-methyl ester
• CAS: 479092-45-0
• 化学式: C₂₀H₂₉ClO₄
• 分子量: 368.901
• InChiKey: MJEVISQNVZYMOJ-SIOLZFAGSA-N

物化性质

• 沸点：
  472.5±45.0 °C(predicted)
• 密度：
  1.050±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E,6E,8E)-4-Chloro-10-eth-(E)-ylidene-2,8-dimethyl-undeca-2,6,8-trienedioic acid 11-tert-butyl ester 1-methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以78%的产率得到(2E,6E,8E)-10-[(E)-ethylidene]-2,8-dimethylundeca-2,4,6,8-tetraenedioic acid 11-tert-butyl ester 1-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：

  (3E,5E)-tert-butyl [(2E)-ethylidene]-4-methyl-9-formyl-octa-3,5-dienate 在 吡啶 、 正丁基锂 、 氯化亚砜 、 间氯过氧苯甲酸 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 (2E,6E,8E)-4-Chloro-10-eth-(E)-ylidene-2,8-dimethyl-undeca-2,6,8-trienedioic acid 11-tert-butyl ester 1-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