8α-formyloxy-14,15-dinorlabdan-13-one | 467251-09-8

• 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: 8α-formyloxy-14,15-dinorlabdan-13-one
• 英文别名: (-)-sclareol；(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(3-oxobutyl)-decahydronaphthalen-2-yl formate；[(1R,2R,4aS,8aS)-2,5,5,8a-tetramethyl-1-(3-oxobutyl)-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-yl] formate
• CAS: 467251-09-8
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: LVMFSGRJDKFVAO-OGWHTMIXSA-N

物化性质

• 沸点：
  376.6±11.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8α-formyloxy-14,15-dinorlabdan-13-one 在 氢氧化钾 、 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 为溶剂， 反应 289.17h， 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
• 作为产物：
  描述：

  香紫苏醇 在 lead(IV) tetraacetate 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以97%的产率得到8α-formyloxy-14,15-dinorlabdan-13-one
  参考文献：
  名称：

  A short synthetic route towards merosesquiterpenes with a benzoxanthene skeleton

  摘要：

  报道了一种从（-）-莽草醇开始制备具有苯并氧黄酮骨架的merosesquiterpenes的简短合成序列。目标化合物的D环通过Diels-Alder环加成获得。

  DOI：

  10.1039/c4cc05116e

文献信息

• First enantiospecific synthesis of marine sesquiterpene quinol akaol A
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Esteban Alvarez、Antonio Fernández、Ramón Alvarez-Manzaneda、Ali Haidour、Jose Miguel Ramos、Ali Akhaouzan

  DOI：10.1039/c1cc14608d

  日期：——

  The first enantiospecific synthesis of akaol A, a marine sesquiterpene quinol, has been achieved. Key steps of the synthetic sequence are the oxidative degradation of (-)-sclareol to a dinorlabdane ketoester, mediated by the ozone-lead(IV) acetate system, the diastereoselective alpha-methylation of a ketoaldehyde, followed by an intramolecular aldol condensation and the further Diels-Alder cycloaddition

  已经实现了第一级对映体合成的akaaka A，一种海洋倍半萜烯喹诺醇。合成序列的关键步骤是（-）-香紫苏醇被臭氧-乙酸铅（IV）系统介导氧化降解为二去甲丹烷酮酸酯，酮醛的非对映选择性α-甲基化，随后分子内羟醛缩合和二烯醇醚的进一步Diels-Alder环加成。
• Preparation of oxocene terpenes. The first enantiospecific synthesis of cytotoxic arenaran A
  作者：Alejandro Torres、Pilar Gutierrez、Ramón Alvarez-Manzaneda、Rachid Chahboun、Enrique Alvarez-Manzaneda

  DOI：10.1039/c6ob01640e

  日期：——

  The first syntheses of cytotoxic marine arenarans A and B starting from commercial (−)-sclareol are reported. The oxocene ring of the target compound is formed via ring-closing metathesis, a process that depends on certain structural requirements. The trans-fused structure of the natural product is confirmed by comparison with the cis-fused isomer, which was synthesized. This synthetic strategy is

  报道了从商业（-）-香紫苏醇开始的细胞毒性海洋arenarans A和B的首次合成。目标化合物的茂新环是通过闭环复分解反应形成的，该过程取决于某些结构要求。通过与合成的顺式融合异构体比较，证实了天然产物的反式融合结构。该合成策略也适用于其他茂新萜烯的合成。
• A short synthetic route towards merosesquiterpenes with a benzoxanthene skeleton
  作者：Antonio Fernández、Esteban Alvarez、Ramón Alvarez-Manzaneda、Rachid Chahboun、Enrique Alvarez-Manzaneda

  DOI：10.1039/c4cc05116e

  日期：——

  A short synthetic sequence for the preparation of merosesquiterpenes with a benzoxanthene skeleton starting from (−)-sclareol is reported. The D ring of the target compound is obtained through a Diels–Alder cycloaddition.

  报道了一种从（-）-莽草醇开始制备具有苯并氧黄酮骨架的merosesquiterpenes的简短合成序列。目标化合物的D环通过Diels-Alder环加成获得。
• 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.