8-Oxo-13,14,15,16,20-pentanorlabdan-12-al | 68982-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-Oxo-13,14,15,16,20-pentanorlabdan-12-al
• CAS: 68982-27-4
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: MRHGILGOWJDYHF-CORIIIEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-Oxo-13,14,15,16,20-pentanorlabdan-12-al 在 吡啶 、 甲醇 、 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 反应 12.0h， 生成 (1R,2S,8aS)-5,5,8a-trimethyl-1-(2-hydroxyethyl)-2-hydroxy-trans-perhydronaphthalene
  参考文献：
  名称：

  Pena, W.; Lopez, J. T.; Cortes, M., Bulletin de la Societe Chimique de France, 1992, # 2, p. 168 - 170

  摘要：

  DOI：
• 作为产物：
  描述：

  (4aS,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-1-methylidene-2(1H)-naphthalenone 在 二异丁基氢化铝 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 55.5h， 生成 8-Oxo-13,14,15,16,20-pentanorlabdan-12-al
  参考文献：
  名称：

  Pena, W.; Lopez, J. T.; Cortes, M., Bulletin de la Societe Chimique de France, 1992, # 2, p. 168 - 170

  摘要：

  DOI：

文献信息

• Total synthesis of (±)-(E)-8β,17-epoxylabd-12-ene-15,16-dial
  作者：Tong Hei Kim、Sachihiko Isoe

  DOI：10.1039/c39830000730

  日期：——

  The title labdanoid dialdehyde (10) which has high antifungal activity was synthesized stereoselectively from the trans-decalone derivative (1).

  具有高抗真菌活性的标题拉丹酰二醛（10）是从反式十烯酮衍生物（1）立体选择性地合成的。
• Studies toward the total synthesis of polyoxygenated labdanes: preliminary approaches
  作者：Denyse Herlem、Jocelyne Kervagoret、Dahai Yu、Françoise Khuong-Huu、Andrew S. Kende

  DOI：10.1016/s0040-4020(01)86264-5

  日期：1993.1

  material, methods are developed for the successive introduction of hydroxy groups at C-6, C-7 and C-8 of a decalin system, as well as for elaboration of a C-9 pentadiene chain in a preliminary approach to the total synthesis of trihydroxylabdadienes.

  以酮基酯3为原料，开发了在十氢化萘系统的C-6，C-7和C-8处连续引入羟基以及精制C-9戊二烯链的方法在初步合成三羟基labdadienes的初步方法中。
• New Diterpenes from<i>Alpinia galanga</i>WILD.
  作者：Hiroshi Morita、Hideji Itokawa

  DOI：10.1246/cl.1986.1205

  日期：1986.7.5

  Two new skeleton diterpenes(galanal A and B) and a new labdane type diterpene were isolated from the seeds of Alpinia galanga WILD.(Zingiberaceae) with (E)-8, 17-epoxy-labd-12-ene-15, 16-dial and their structures were established by the spectral evidences.

  用(E)-8, 17-epoxy-labd-12-ene-15, 16-从高良姜科(Zingiberaceae)种子中分离得到两种新型骨架二萜(galanal A和B)和一种新型劳丹脂型二萜。表盘及其结构是由光谱证据确定的。
• Conversion of sclareol into (+)-galanolactone and (+)-labdienedial
  作者：Mankil Jung、Seokjoon Lee、Byunghee Yoon

  DOI：10.1016/s0040-4039(97)00485-1

  日期：1997.4

  A short, regiospecific and first synthesis of (+)-galanolactone 5 and (+)labdienedial 1 1 was achieved from sclareol, respectively. (C) 1997 Elsevier Science Ltd.
• Bioactive Labdane Diterpenoids from <i>Renealmia alpinia</i> Collected in the Suriname Rainforest
  作者：Bing-Nan Zhou、Nina J. Baj、Thomas E. Glass、Stan Malone、Marga C. M. Werkhoven、Frits van Troon、David、Jan H. Wisse、David

  DOI：10.1021/np970233c

  日期：1997.12.1

  The preservation of tropical rainforests is an important goal both for the intrinsic value of their cultural and biological diversity as well as for the well-being of the peoples who make these forests their home. In addition, tropical forests are potential sources of new pharmaceutical products that can only be found by chemical prospecting in Nature's genetically encoded combinatorial library. As part of an effort to integrate biodiversity conservation and drug discovery with economic development, we have initiated a collaborative program to discover potential pharmaceuticals in the rainforest of Suriname. The plant Renealmia alpinia (Zingiberaceae) was selected for investigation based on its ethnomedical use as a febrifuge, but testing in the yeast Sc-7 assay gave a positive response, indicative of cytotoxic activity. Using this bioassay, the two new labdane diterpenes, 11-hydroxy-8(17),12(E)-labdadien-15,-16-dial 11,15-hemiacetal(1) and 16-oxo-8(17),12(E)-labdadien-15-oic acid (2), and the known diterpene, 8(17),12(E)-labdadien-15,16-dial (3), have been isolated. Their structures were elucidated by 1D and 2D NMR techniques (DEFT, COSY, HETCOR, HMBC, and NOESY) and IR, UV, and MS spectra, and the absolute stereochemistry of 1 was established by CD spectroscopy and by the formation and NMR analysis of alpha-methoxyphenylacetyl esters. The hemiacetal 1 was cytotoxic to M109 cells, with an IC50 value of 2.6 mu g/mL.