farnesiferol C | 512-17-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: farnesiferol C
• 英文别名: 7-[(E)-3-methyl-5-[(1S,2R,4R)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]pent-2-enoxy]chromen-2-one
• CAS: 512-17-4
• 化学式: C₂₄H₃₀O₄
• 分子量: 382.5
• InChiKey: OCHZHKVSLMBEJP-QYQYHAIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为产物：
  描述：

  kopeolone 在 sodium tetrahydroborate 、 硫酸 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 1.25h， 生成 farnesiferol C
  参考文献：
  名称：

  A new terpenoid coumarin fromFerula kopetdaghensis

  摘要：

  DOI：

  10.1007/bf00581594

文献信息

• Zeolite NaY‐Promoted Monocyclization of Epoxy Polyene Terpenes: A Unique Route for the Direct Synthesis of Incompletely Cyclized Naturally Occurring Terpenols
  作者：Constantinos Tsangarakis、Christos Raptis、Elias Arkoudis、Manolis Stratakis

  DOI：10.1002/adsc.200800180

  日期：2008.7.7

  the brown algae Cystophora monoliformis. The optical rotation of achilleol A derived from the cyclization of (S)-2,3-epoxysqualene matches with that of the natural product, thus the absolute configuration of achilleol A was established as 1S,3R. From the mechanistic point of view, the NaY-promoted cyclization of 9,10-epoxygeranylacetone, selectively deuterium labelled at the C-10 methyl group, is >97%

  通过限制在NaY沸石中，各种环氧多烯萜容易环化，主要形成单环化产物。不管环氧萜烯的侧链如何，单环化途径都非常占优势，而单环产物具有区域选择性地具有外亚甲基双键。在乙酸法呢烯基乙酸酯，环氧法呢烯基丙酮或2,3-环氧角鲨烯的情况下，选择性单环化为合成多种天然产物（例如榄香二醇，法呢香酚B–D，阿奇儿醇A，山茶酚C和四种法呢基丙酮）提供了直接途径。褐藻中提取的代谢产物。由（S的环化引起的Achilleol A的旋光。基）-2,3-环氧角鲨烯与天然产物的匹配，从而achilleol A的绝对构型确定为1小号，3 - [R 。从机理的角度来看，NaY促进的9,10-环氧香叶基丙酮（在氘代C-10甲基上进行选择性氘标记）的环化相对于宝石-二甲基基团的局部立体选择性> 97％。这一结果与协调机制相吻合。最后，我们首次通过标记实验证明，环氧多烯萜烯在酸催化下向2,3,4-三甲基环己酮的仿生转化是高度立体选
• Regio- and Stereoselective Syntheses of 7-Oxabicyclo[2.2.1]heptanes <i>via</i> a Gold(I)-Catalyzed Cycloisomerization of Alkynediols: Asymmetric Total Synthesis of Farnesiferol C
  作者：Yue-Qing Gu、Peng-Peng Zhang、Jun-Kai Fu、Song Liu、Yu Lan、Jian-Xian Gong、Zhen Yang

  DOI：10.1002/adsc.201600218

  日期：2016.4.28

  7‐oxabicyclo[2.2.1]heptanes, which proceeds through a sequential reaction involving gold(I)‐catalyzed cycloisomerization of alkynediols and sequential semi‐pinacol‐type 1,2‐alkyl migration, was developed. The developed chemistry was applied to the asymmetric total synthesis of the natural product farnesiferol C.

  一种高度区域选择性和立体选择性的方法，可构建广泛的7-氧杂双环[2.2.1]庚烷，该过程通过涉及炔烃的金（I）催化的环异构化和顺序的半频哪醇型1,2-的顺序反应进行烷基迁移。已开发的化学方法可用于天然产物法尼醇C的不对称全合成。
• Selective Monocyclization of Epoxy Terpenoids Promoted by Zeolite NaY. A Short Biomimetic Synthesis of Elegansidiol and Farnesiferols B−D
  作者：Constantinos Tsangarakis、Elias Arkoudis、Christos Raptis、Manolis Stratakis

  DOI：10.1021/ol062798i

  日期：2007.2.1

  Epoxy terpenes cyclize readily, by confinement within zeolite NaY, to form exomethylenic cyclohexanols as the major products. The selective monocyclization of 10,11-epoxyfarnesyl acetate within NaY provides a short and efficient biomimetic route to (+/-)-elengasidiol and (+/-)-farnesiferols B-D.
• Unexpected Rearrangement in the Peroxytrifluoroacetic Acid-Mediated Baeyer-Villiger Oxidation of trans-3.beta.-Hydroxy-4,4,10.beta.-trimethyl-9-decalone Forming a 7-Oxabicyclo[2.2.1]heptane. Structure Proof and Total Synthesis of (.+-.)-Farnesiferol-C
  作者：F. W. Joachim Demnitz、Cristiane Philippini、Ralph A. Raphael

  DOI：10.1021/jo00121a032

  日期：1995.8

  A rearrangement in the Baeyer-Villiger oxidation of trans- 3 beta-hydroxy-4,4,10 beta-trimethyl-9-decalone (2a) and of OCH(2)OMe (2b) and OTHP (2c) derivatives using peroxytrifluoroacetic acid is reported. The reaction involves trifluoroacetic acid catalyzed rearrangement-of the initially formed hydroxy lactone 5a giving the 7-oxabicyclo[2.2.1]heptane carboxylic acid 6. This unexpected rearrangement is a useful preparation of the 7-oxabicyclo[2.2.1]heptane ring system and constitutes a stereoselective synthesis of the left-hand portion of the sesquiterpene-coumarin ether (+/-)-farnesiferol-C (10). The product 6 serves as an advanced, key intermediate from which a total synthesis and structure proof of this natural product is presented.