(1S,6R,7R)-1-甲基-7-(3-氧代丁基)-4-丙-2-亚基双环[4.1.0]庚烷-3-酮 | 100347-96-4

• 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
• 中文名称: (1S,6R,7R)-1-甲基-7-(3-氧代丁基)-4-丙-2-亚基双环[4.1.0]庚烷-3-酮
• 英文名称: curcumenone
• 英文别名: Bicyclo(4.1.0)heptan-3-one, 1-methyl-4-(1-methylethylidene)-7-(3-oxobutyl)-, (1S,6R,7R)-；(1S,6R,7R)-1-methyl-7-(3-oxobutyl)-4-propan-2-ylidenebicyclo[4.1.0]heptan-3-one
• CAS: 100347-96-4
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: HUZJLWLCLJEXEL-NFAWXSAZSA-N

物化性质

• 沸点：
  343.7±11.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• LogP：
  1.043 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

制备方法与用途

莪术双环烯酮是一种环酮类有机化合物，可用作含量测定、鉴定以及药理实验的参考。

反应信息

• 作为反应物：
  描述：

  (1S,6R,7R)-1-甲基-7-(3-氧代丁基)-4-丙-2-亚基双环[4.1.0]庚烷-3-酮 在 palladium hydroxide - carbon 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三氟甲磺酸三甲基硅酯 、 CeCl₂*H₂O 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 35.33h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,3S,4R,6R,7R)-4-isopropyl-1-methyl-7-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-bicyclo[4.1.0]hept-3-yl ester
  参考文献：
  名称：

  Absolute stereostructure of carabrane-type sesquiterpene and vasorelaxant-active sesquiterpenes from Zedoariae Rhizoma

  摘要：

  The aqueous acetone extract of Zedoariae Rhizoma was found to show inhibitory effects on contractions induced by high concentrations of potassium cation (K+) in isolated rat aortic strips. From the extract, two new carabrane-type sesquiterpenes, curcarabranols A and B, were isolated together with a few carabrane-type sesquiterpenes, such as curcumenone and 4S-dihydrocurcumenone. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence, which included the application of the modified Mosher's method and chemical conversion from curcumenone to curcarabranols A and B. In addition, several sesquiterpenes and diaryl-heptanoids (e.g. germacrone, glechomanolide, isocurucmenol, beta -eudesmol, and beta -dictyopterol) showed potent inhibitory effects on contractions induced by high concentrations of K+ in isolated rat aortic strips (inhibition > 80% at 100 muM), while they did not inhibit norepinephrine-induced contractions, so that the vasorelaxant activities of these sesquiterpenes were presumed to be dependent on their calcium channel-blocking activity. (C) 2001 Elsevier Science Ltd. AE rights reserved.

  DOI：

  10.1016/s0040-4020(01)00828-6
• 作为产物：
  描述：

  (4S)-二氢莪术双环烯酮 在 吡啶 、 chromium(VI) oxide 作用下， 以100%的产率得到(1S,6R,7R)-1-甲基-7-(3-氧代丁基)-4-丙-2-亚基双环[4.1.0]庚烷-3-酮
  参考文献：
  名称：

  Absolute Stereostructures of Carabrane-Type Sesquiterpenes, Curcumenone, 4S-Dihydrocurcumenone, and Curcarabranols A and B: Vasorelaxant Activity of Zedoary Sesquiterpenes.

  摘要：

  从莪术中分离出了新的莪术酚 A 和 B，以及两种已知的莪术酮和 4S- 二氢莪术酮。根据物理化学和化学证据确定了这些石榴烯类倍半萜的绝对立体结构。研究发现，包括 4S- 二氢莪术酮和莪术醇 A 和 B 在内的泽泻烯类倍半萜能抑制高浓度 K+ 在离体大鼠主动脉条带上引起的收缩。

  DOI：

  10.1248/cpb.46.1186

文献信息

• Structural determination of two new sesquiterpenes biotransformed from germacrone byMucor alternata
  作者：Niu Jia、MA Xiao Chi、Xin Xiu Lan、Jin Hong Wei、Guo Dean

  DOI：10.1002/mrc.2148

  日期：2008.2

  Eight transformed sesquiterpenes of germacrone by Mucor alternata were obtained. Their structures were characterized on the basis of spectral methods including 2D NMR. Among them, (1S, 4S, 5S, 10R)‐isozedoarondiol (2) and (1R, 4S, 5S, 10R)‐diepoxy‐12‐hydroxygermacrone (3) are new compounds. Copyright © 2007 John Wiley & Sons, Ltd.

  获得了八株由互生毛霉转化的杰马克酮倍半萜。它们的结构基于包括 2D NMR 在内的光谱方法进行了表征。其中，(1S, 4S, 5S, 10R)-isozedoarondiol (2) 和 (1R, 4S, 5S, 10R)-diepoxy-12-hydroxygermacrone (3) 是新化合物。版权所有 © 2007 John Wiley & Sons, Ltd.
• Biotransformation of sesquiterpenes by cultured cells ofCurcuma zedoaria
  作者：Norihiro Sakui、Masanori Kuroyanagi、Yoko Ishitobi、Makoto Sato、Akira Ueno

  DOI：10.1016/0031-9422(91)83023-e

  日期：1992.1

  Abstract The transformation of a 10-membered ring sesquiterpene, germacrone, into guaiane-type sesquiterpenes by suspension cultured cells ofCurcuma zedoaria was investigated. Germacrone was converted into several sesquiterpenes, some of which were isolated from theCurcuma spp. plants through, the key intermediate, (4R,5R)-germacrone 4,5-epoxide, and their structures were determined by spectral and

  摘要 研究了莪术悬浮培养细胞将十元环倍半萜基麦角酮转化为愈创木酚型倍半萜。Germacrone 被转化为几种倍半萜，其中一些是从 Curcuma spp 中分离出来的。植物通过关键中间体 (4R,5R)-germacrone 4,5-epoxide，通过光谱和化学证据确定了它们的结构。一些衍生物的构型与从姜黄属植物中分离的倍半萜的构型相反。芳香族，C. 龙加和C。芹菜。还分离了一种eudesmane 型产品并确定了其结构。从结构上推测，germacrone 通过中间体 (1S, 10S)-germacrone 1,10-epoxide 转化，并通过germacrone 1 的转化进一步证实，10-环氧化物经酸处理成同品。还确定了两种新产品的结构，并推导了它们通过姜黄酮和二氢姜黄酮的转化机制。
• Biotransformation of germacrone by suspension cultured cells
  作者：Shiho Sakamoto、Naoko Tsuchiya、Masanori Kuroyanagi、Akira Ueno

  DOI：10.1016/s0031-9422(00)94823-4

  日期：1994.3

  Abstract The transformation of germacrone, a 10-membered ring sesquiterpene, by suspension cultured cells of Lonicera japonica, Bupleurum falcatum, Polygonum tinctorium and solidago altissima , was investigated. Germacrone was converted into several types of sesquiterpenes, such as guaiane, eudesmane and seco-guaiane and their structures were determined from spectral and chemical evidence. The configurations

  摘要 研究了金银花、柴胡、何首乌和一枝黄花悬浮培养细胞对10元环倍半萜基麦角酮的转化。Germacrone 被转化为几种类型的倍半萜，如愈创木、eudesmane 和 seco-guaiane，它们的结构由光谱和化学证据确定。一些产品的构型是通过 CD 光谱确定的。讨论了四种悬浮培养细胞在产品种类上的差异。
• Direct chemical derivatization of natural plant extract: straightforward synthesis of natural plant-like hydantoin
  作者：Keisuke Tomohara、Tomohiro Ito、Naoto Hasegawa、Atsushi Kato、Isao Adachi

  DOI：10.1016/j.tetlet.2016.01.054

  日期：2016.2

  The direct chemical derivatization of natural plant extracts that would enable the straightforward synthesis of natural plant-like molecules seemed to be far from reality due primarily to the inherently complex chemical property of the extract. After model studies, the envisioned derivatization was realized under the rationally designed Bucherer–Bergs reaction conditions to afford unnatural hydantoin

  天然植物提取物的直接化学衍生化将使天然植物样分子的直接合成成为现实，这似乎还远远没有实现，这主要是由于提取物固有的复杂化学性质。经过模型研究，可以在合理设计的Bucherer-Bergs反应条件下实现预想的衍生化反应，以从姜黄姜黄乙酸乙酯提取物中提供带有四取代碳的非天然乙内酰脲。反应以足够的化学选择性进行，从而通过可靠的光谱分析指导从混合物中鉴定出所需的产物。
• Transdermal delivery of pharmaceutical agents
  申请人：Russell-Jones J. Gregory

  公开号：US20070243132A1

  公开（公告）日：2007-10-18

  The present invention generally relates to a vehicle useful for delivering a pharmaceutically active compound including a genetic molecule or composition. More particularly, the present invention provides microemulsions for transdermal delivery of pharmaceutically active agents to a subject.

  本发明通常涉及一种用于传递包括遗传分子或组成的药物活性化合物的车辆。更具体地，本发明提供了微乳液，用于经皮途径向受体传递药物活性剂。