(1R,2R,4R,5R,1'S,2'R,5'S)-4-hydroxy-5-phenylselanyl-cyclohexane-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester | 479549-19-4

• 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: (1R,2R,4R,5R,1'S,2'R,5'S)-4-hydroxy-5-phenylselanyl-cyclohexane-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester
• 英文别名: bis[(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexyl] (1R,2R,4R,5R)-4-hydroxy-5-phenylselanylcyclohexane-1,2-dicarboxylate
• CAS: 479549-19-4
• 化学式: C₃₄H₅₂O₅Se
• 分子量: 619.744
• InChiKey: HXBKSQZIOCFPIU-XUBUVNJUSA-N

物化性质

• 熔点：
  130-131 °C
• 沸点：
  651.3±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,4R,5R,1'S,2'R,5'S)-4-hydroxy-5-phenylselanyl-cyclohexane-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester 在 二异丙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以92%的产率得到(1R,2R,3Z,5R,1'S,2'R,5'S)-5-hydroxy-cyclohex-3-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester
  参考文献：
  名称：

  Total synthesis of the polyenoyltetramic acid polycephalin C

  摘要：

  The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction has been determined by synthesis of both isomers and comparison of their CD spectra with natural polycephalin C. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00816-0
• 作为产物：
  描述：

  D-薄荷醇 在 吗啉 、 氯化二乙基铝 、 对甲苯磺酸 作用下， 以 正己烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 75.67h， 生成 (1R,2R,4R,5R,1'S,2'R,5'S)-4-hydroxy-5-phenylselanyl-cyclohexane-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester
  参考文献：
  名称：

  Total synthesis of the polyenoyltetramic acid polycephalin C

  摘要：

  The total synthesis of the polyenoyltetramic acid polycephalin C is described. Key steps of the synthesis include a double Swern oxidation, double Takai reaction and a double Stille reaction. In addition, the absolute stereochemistry of the ring junction has been determined by synthesis of both isomers and comparison of their CD spectra with natural polycephalin C. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00816-0

文献信息

• Total Synthesis of Polycephalin C and Determination of the Absolute Configurations at the 3″,4″ Ring Junction
  作者：Deborah A. Longbottom、Angus J. Morrison、Darren J. Dixon、Steven V. Ley

  DOI：10.1002/1521-3773(20020802)41:15<2786::aid-anie2786>3.0.co;2-z

  日期：2002.8.2