3β-<2-Hydroxy-propyl-(2)>-5-oxo-9β-methyl-trans-dekalin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3β-<2-Hydroxy-propyl-(2)>-5-oxo-9β-methyl-trans-dekalin
• 英文别名: (4aR,7R,8aR)-7-(2-hydroxypropan-2-yl)-4a-methyl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-one
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: BQHVYLSLRVDWHX-UHIISALHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-<2-Hydroxy-propyl-(2)>-5-oxo-9β-methyl-trans-dekalin 在 咪唑 、 六甲基磷酰三胺 、 四(三苯基膦)钯 、 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 r-eudesmol
  参考文献：
  名称：

  A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol

  摘要：

  The ether extract of the liverwort Porella perrottetiana afforded (-)-alpha-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (-)-alpha-eudesmol strongly suggested that the positive values (e.g. + 28.5 degrees) described in many previous papers should be revised. Since the absolute configuration of (-)-alpha-eudesmol was identical to that of (+)-beta-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (-)-alpha-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (-)-alpha-eudesmol will be discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00299-x
• 作为产物：
  描述：

  4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮 在 五氯化磷 作用下， 反应 2.0h， 生成 3β-<2-Hydroxy-propyl-(2)>-5-oxo-9β-methyl-trans-dekalin
  参考文献：
  名称：

  倍半萜—III：杜仲倍半萜的全合成

  摘要：

  （±_-β-Eudesmol（1）已从八酮2以高度立体选择性的10阶段路线合成。几种合成中间体可能是用于合成其他杜仲倍半萜类化合物的潜在有用化合物。

  DOI：

  10.1016/s0040-4020(01)82485-6

文献信息

• Functionalisation of saturated hydrocarbons. Part XI. Oxidation of cedrol, ?- and ?-eudesmol, sclareol, manoyl oxide, 1,9-dideoxyforskolin, methyltrans-dihydroiasmonate, and tetrahydrolinalool by the ?Gif system?
  作者：Derek H. R. Barton、Jean-Clauude Beloeil、Annick Billion、Jean Boivin、Jean-Yves Lallemand、Patrick Lelandais、Simone Mergui

  DOI：10.1002/hlca.19870700824

  日期：1987.12.16

  The oxidation of cedrol (1), β- and γ-eudesmol (6 and 7, resp.), sclareol (14) manoyl oxide (15), 1,9-dideoxyforskolin (22) (±)-methyl trans-dihydrojasmonate (28), and tetrahydrolinalool (32) nearly all of natural terpenoid origin, by the ‘Gif system’ has afforded a number of novel products (3, 11, and 12, 16/17, 18/19, 26, 29–31, and ketones corresponding to 34–35, res.). The structures of these compounds

  头孢（1），β-​​和γ-地摩尔（分别为6和7），香紫苏醇（14）氧化锰（15），1,9-二脱氧伏夫林（22）（±）-反式-二氢茉莉酸甲酯（（1））的氧化。28），和四氢芳樟醇（32）几乎所有天然萜类来源的，由'的Gif系统'已经得到了许多的新产品（的3，11，和12，16/17，18/19，26，29-31，和对应于34–35的酮，res。）。这些化合物的结构是通过包括2D-NMR在内的光谱技术确定的，并在适当情况下通过与真实样品进行比较来确定。
• Terpenoids—XCVIII
  作者：R.K. Mathur、A.S. Rao

  DOI：10.1016/0040-4020(67)85076-2

  日期：1967.1

  The title compounds have been synthesized. The Huang-Minlon reduction of ketoalcohol XVI has been studied. Improved methods for the preparation of 2-methylcyclohexane-1,4-dione and 4,4-ethylenedioxy-2-methylcyclohexanone have been developed.

  标题化合物已经合成。研究了酮醇XVI的Huang-Minlon还原。已经开发了制备2-甲基环己烷-1，4-二酮和4，4-乙烯二氧基-2-甲基环己酮的改进方法。
• Structures and Spasmolytic Activities of Derivatives from Sesquiterpenes of Alpinia speciosa and Alpinia japonica.
  作者：Makoto MORITA、Hiroshi NAKANISHI、Hiroshi MORITA、Susumu MIHASHI、Hideji ITOKAWA

  DOI：10.1248/cpb.44.1603

  日期：——

  Sesquiterpenes isolated from Alpinia speciosa and Alpinia japonica, and their derivatives were found to inhibit histamine- or barium chloride-induced contraction of excised guinea pig ileum when tested by the Magnus method. Major spasmolytic principles contained in those extracts were the sesquiterpenes, β-eudesmol, nerolidol, humulene epoxide II and 4α-hydroxydihydroagarofuran. Relationships between the chemical structures of the sesquiterpenes and their derivatives, and their spasmolytic activities were discussed.

  通过马格努斯法测试发现，从白山药和白山药中分离出的倍半萜及其衍生物可抑制组胺或氯化钡引起的切除豚鼠回肠收缩。这些提取物所含的主要解痉成分是倍半萜、β-桉叶油醇、橙花叔醇、环氧化葎草烯 II 和 4α-羟基二氢豨莶草醚。讨论了倍半萜及其衍生物的化学结构与它们的解痉活性之间的关系。
• The absolute configuration of eudesmane-type sesquiterpenoids found in the Japanese liverwort Chiloscyphus polyanthos
  作者：M Toyota、T Saito、Y Asakawa

  DOI：10.1016/s0031-9422(99)00159-4

  日期：1999.8

  The ether extract of the liverwort Chiloscyphus polyanthos afforded sesquiterpenoids which are enantiomeric to those found in another liverwort Lepidozia vitrea. The absolute configurations of the sesquiterpenoids found in the title species were determined by spectroscopic evidence, chemical derivatization and /or X-ray crystallographic analysis.

  地草 Chiloscyphus polyanthos 的醚提取物提供了倍半萜类化合物，其与另一种地草 Lepidozia vitrea 中发现的化合物是对映异构体的。在标题物种中发现的倍半萜类化合物的绝对构型是通过光谱证据、化学衍生化和/或 X 射线晶体学分析确定的。
• Sugii; Shindo, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1930, vol. 50, p. 709,711; dtsch. Ref. S. 103
  作者：Sugii、Shindo

  DOI：——

  日期：——