14,15-dinorlabd-8-en-13-ol | 960116-67-0

• 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: 14,15-dinorlabd-8-en-13-ol
• CAS: 960116-67-0；54169-34-5；54169-37-8
• 化学式: C₁₈H₃₂O
• 分子量: 264.451
• InChiKey: NYGNKEIXNFJKQB-RNYWFIABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  14,15-dinorlabd-8-en-13-ol 、 乙酸酐 在 吡啶 作用下， 反应 6.0h， 以98%的产率得到13-acetoxy-14,15-dinor-8-labdene
  参考文献：
  名称：

  Synthetic studies to highly functionalised B ring labdanes

  摘要：

  Several 6,7-dioxygenated (cis or trans) labdanes have been synthesised starting front sclareol. A new strategy that allows the obtention of diols alpha-cis as well as beta-cis of trans is described. In particular, the syntheses of three natural highly functionalised labdanes in the B rings of 2, 3 and 4 with different side chains are reported. The syntheses have permitted to Correct the proposed Structure for one of them. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.083
• 作为产物：
  描述：

  15,16-dinor-labd-8-en-13-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以99%的产率得到14,15-dinorlabd-8-en-13-ol
  参考文献：
  名称：

  Synthetic studies to highly functionalised B ring labdanes

  摘要：

  Several 6,7-dioxygenated (cis or trans) labdanes have been synthesised starting front sclareol. A new strategy that allows the obtention of diols alpha-cis as well as beta-cis of trans is described. In particular, the syntheses of three natural highly functionalised labdanes in the B rings of 2, 3 and 4 with different side chains are reported. The syntheses have permitted to Correct the proposed Structure for one of them. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.083

文献信息

• Polyene cyclizations using mercury (II) triflate-N,N-dimethylaniline complex - participation by internal nucleophiles
  作者：Aravamudan S. Gopalan、Robert Prieto、Britta Mueller、David Peters

  DOI：10.1016/s0040-4039(00)91704-0

  日期：1992.3

  The cyclization of a number of functionalized polyenes with mercuric triflate - N,N-dimethylaniline complex (Nishizawa's reagent) to give bicyclic or tricyclic products has been studied. Suitably positioned internal nucleophiles, such as carbonyl, hydroxy and β-ketoester groups were found to participate to varying extent, in the termination of these cyclizations.

  已经研究了使用三氟甲磺酸汞-N，N-二甲基苯胺络合物（西泽试剂）将许多官能化多烯环化以生成双环或三环产物的方法。发现合适定位的内部亲核试剂，例如羰基，羟基和β-酮酸酯基团在这些环化的终止中以不同程度参与。
• Synthesis of (+)-lagerstronolide from (+)-sclareol
  作者：Pilar Basabe、Olga Bodero、Isidro S. Marcos、David Diez、Mónica de Román、Araceli Blanco、Julio G. Urones

  DOI：10.1016/j.tet.2007.09.036

  日期：2007.11

  The gamma-acetoxybutenolide (+)-lagerstronolide was synthesized from (+)-sclareol, with an overall yield of 10%. The absolute stereochemistry for the natural compound (-)-lagerstronolide has been correctly established. (c) 2007 Elsevier Ltd. All rights reserved.