methyl 12-hydroxy-13,14,15,16-tetranorlabd-8(17)-en-19-oate | 39668-53-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 12-hydroxy-13,14,15,16-tetranorlabd-8(17)-en-19-oate
• 英文别名: methyl (1S,4aR,5S,8aR)-5-(2-hydroxyethyl)-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 39668-53-6
• 化学式: C₁₇H₂₈O₃
• 分子量: 280.408
• InChiKey: WURXPHFHXKVWFD-ABFRBSLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 12-hydroxy-13,14,15,16-tetranorlabd-8(17)-en-19-oate 在 氢氧化钾 、 lithium aluminium tetrahydride 、 jones reagent 、 对甲苯磺酸 、 一水合肼 作用下， 以 四氢呋喃 、 硝基甲烷 、 丙酮 为溶剂， 反应 5.5h， 生成 降龙涎香醚
  参考文献：
  名称：

  Synthesis of Ambrox® from communic acids

  摘要：

  Two routes for preparing Ambrox(R) (1) from the methyl esters of trans-communic acid (2b) and/or cis-communic acid (3b), via selective degradation of their side chains, stereoselective formation of the tetrahydrofurane ring, and reduction of the axial methoxycarbonyl group, are described.

  DOI：

  10.1016/s0040-4020(01)87963-1
• 作为产物：
  描述：

  (E)-methyl communate 在 lithium aluminium tetrahydride 、 氧气 、 臭氧 作用下， 生成 methyl 12-hydroxy-13,14,15,16-tetranorlabd-8(17)-en-19-oate
  参考文献：
  名称：

  Synthesis of Ambrox® from communic acids

  摘要：

  Two routes for preparing Ambrox(R) (1) from the methyl esters of trans-communic acid (2b) and/or cis-communic acid (3b), via selective degradation of their side chains, stereoselective formation of the tetrahydrofurane ring, and reduction of the axial methoxycarbonyl group, are described.

  DOI：

  10.1016/s0040-4020(01)87963-1

文献信息

• Diastereoselective Intramolecular Heck Reaction Assisted by an Acetate Group: Synthesis of the Decahydrobenzofluorene Derivative Dasyscyphin E
  作者：Fermín Jiménez、Antonio Fernández、Ettahir Boulifa、Ahmed Ibn Mansour、Ramón Alvarez-Manzaneda、Rachid Chahboun、Enrique Alvarez-Manzaneda

  DOI：10.1021/acs.joc.7b01551

  日期：2017.9.15

  The first synthesis of antifungal sesquiterpene quinol dasyscyphin E was achieved starting from trans-communic acid. The process described involves the first diastereoselective synthesis of this type of compound by cyclization of an aryl bicyclosesquiterpene. The acid was efficiently transformed into a sesquiterpene synthon, which was converted into the corresponding bromoaryl sesquiterpene. The key

  抗真菌倍半萜烯喹啉dasyscyphin E的第一个合成是从反式-交流酸开始的。所描述的方法涉及通过芳基双环倍半萜烯的环化来进行这种类型化合物的第一次非对映选择性合成。该酸被有效地转化为倍半萜烯合成子，后者被转化为相应的溴芳基倍半萜烯。合成序列的关键步骤是后者在Heck反应条件下的环化，产生具有完全非对映选择性的目标化合物的四环骨架。乙酸酯基团的参与对于Heck反应的过程和该方法的立体选择性都是决定性的。
• Cambie, Richard C.; Clark, George R.; Goeth, Michelle E., Australian Journal of Chemistry, 1989, vol. 42, # 4, p. 497 - 510
  作者：Cambie, Richard C.、Clark, George R.、Goeth, Michelle E.、Rickard, Clifton E.F.、Rutledge, Peter S.、et al.

  DOI：——

  日期：——
• CAMBIE, RICHARD C.;CLARK, GEORGE R.;GOETH, MICHELLE E.;RICKARD, CLIFTON E+, AUSTRAL. J. CHEM., 42,(1989) N, C. 497-509
  作者：CAMBIE, RICHARD C.、CLARK, GEORGE R.、GOETH, MICHELLE E.、RICKARD, CLIFTON E+

  DOI：——

  日期：——
• Synthesis of Ambrox® from communic acids
  作者：Alejandro F. Barrero、Joaquín Altarejos、Enrique J. Alvarez-Manzaneda、José M. Ramos、Sofía Salido

  DOI：10.1016/s0040-4020(01)87963-1

  日期：1993.7

  Two routes for preparing Ambrox(R) (1) from the methyl esters of trans-communic acid (2b) and/or cis-communic acid (3b), via selective degradation of their side chains, stereoselective formation of the tetrahydrofurane ring, and reduction of the axial methoxycarbonyl group, are described.