methyl 5-[(1R,2R,4aS,8aS)-2-formyloxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoate

• 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: methyl 5-[(1R,2R,4aS,8aS)-2-formyloxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoate
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: CEHXOVCCJGHXEP-GKJHBJHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-[(1R,2R,4aS,8aS)-2-formyloxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoate 在 氢氧化钾 、 potassium permanganate 、 magnesium sulfate 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 硝基甲烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 289.92h， 生成 降龙涎香醚
  参考文献：
  名称：

  Synthesis of Ambrox® from labdanolic acid

  摘要：

  A synthesis of the valuable amber-type odorant Ambrox(R) from labdanolic acid (main diterpenoid of the acid fraction of nonpolar extracts of Cistus ladaniferus L.) is reported. The conversion is based on (a) the alpha,beta-dehydrogenation of methyl labdanolate using an organoselenium reagent, (b) subsequent oxidative degradations of the side chain, and (c) final acid-promoted cyclization of the resulting tetranorlabdan-8alpha,12-diol. The influence of the temperature and solvent in the cyclization of the diol with p-toluenesulfonic acid is also described. Thus, Ambrox(R) has been obtained by a six-step procedure in 33% overall yield from methyl labdanolate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00571-9

文献信息

• Synthesis of Ambrox® from labdanolic acid
  作者：Juan M Castro、Sofı́a Salido、Joaquı́n Altarejos、Manuel Nogueras、Adolfo Sánchez

  DOI：10.1016/s0040-4020(02)00571-9

  日期：2002.7

  A synthesis of the valuable amber-type odorant Ambrox(R) from labdanolic acid (main diterpenoid of the acid fraction of nonpolar extracts of Cistus ladaniferus L.) is reported. The conversion is based on (a) the alpha,beta-dehydrogenation of methyl labdanolate using an organoselenium reagent, (b) subsequent oxidative degradations of the side chain, and (c) final acid-promoted cyclization of the resulting tetranorlabdan-8alpha,12-diol. The influence of the temperature and solvent in the cyclization of the diol with p-toluenesulfonic acid is also described. Thus, Ambrox(R) has been obtained by a six-step procedure in 33% overall yield from methyl labdanolate. (C) 2002 Elsevier Science Ltd. All rights reserved.