(1S,8aR)-1-异丙基-4,7-二甲基-1,2,3,5,6,8a-六氢萘 | 483-76-1

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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,8aR)-1-异丙基-4,7-二甲基-1,2,3,5,6,8a-六氢萘
• 中文别名: Δ-杜松烯
• 英文名称: delta-cadinene
• 英文别名: (1S-cis-)-1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-naphthalene；(1S-cis)-1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-naphthalene；(1S,cis)-1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene；1,2,3,5,6,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene；δ‐cadinene；(+)-delta-Cadinene；(1S,8aR)-4,7-dimethyl-1-propan-2-yl-1,2,3,5,6,8a-hexahydronaphthalene
• CAS: 483-76-1
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: FUCYIEXQVQJBKY-ZFWWWQNUSA-N

物化性质

• 沸点：
  277.87°C (rough estimate)
• 密度：
  0.9160
• 闪点：
  38 °C
• 溶解度：
  DMF: 30 mg/ml,DMSO: 30 mg/ml,乙醇: 30 mg/ml,PBS (pH 7.2): 1 mg/ml
• LogP：
  6.271 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R10,R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  UN 2319 3/PG 3
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P331,P301+P310,P405
• 危险性描述：
  H304

制备方法与用途

Δ-杜松烯主要来源于烤烟烟叶、白肋烟烟叶和香料烟烟叶。

反应信息

• 作为反应物：
  描述：

  (1S,8aR)-1-异丙基-4,7-二甲基-1,2,3,5,6,8a-六氢萘 在 recombinant (+)-δ-cadinene hydroxylase 作用下， 反应 1.5h， 生成 (+)-8-hydroxy-δ-cadinene
  参考文献：
  名称：

  8-Hydroxy-(+)- δ -cadinene is a precursor to hemigossypol in Gossypium hirsutum

  摘要：

  [H-3](+)-delta-Cadinene and its 8-hydroxy derivative, prepared from (1RS)-[1-H-3]FPP by the action of one and two recombinant enzymes, respectively, were infiltrated into cotyledons of bacterial blight-resistant cotton plants as they biosynthesized sesquiterpene phytoalexins in response to infection by Xanthomonas campestris pv. malvacearum. Following both treatments, tritium appeared in the HPLC fraction that contained hemigossypol. Hemigossypol was isolated from the cotyledons that had been treated with [H-3](+)-8-hydroxy-delta-cadinene and was trimethylsilylated and purified. In two experiments, specific radioactivity of the hemigossypol derivative indicated that 5% and 10%, respectively, of the [H-3](+)-8-hydroxy-delta-cadinene had been converted to hemigossypol. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00270-x
• 作为产物：
  描述：

  farnesyl pyrophosphate 在 δ-cadinene synthase 作用下， 以98%的产率得到(1S,8aR)-1-异丙基-4,7-二甲基-1,2,3,5,6,8a-六氢萘
  参考文献：
  名称：

  δ-卡二烯合酶的 β 结构域中的氨基末端片段对催化至关重要†

  摘要：

  尽管距离活性位点很远，但植物倍半萜环化酶 δ-卡二烯合酶 (DCS) β 结构域中的柔性氨基末端片段 (NTS) 对于催化过程中的活性位点关闭和去溶剂化事件至关重要。

  DOI：

  10.1039/c6ob01398h

文献信息

• Sesquiterpene Synthases Cop4 and Cop6 from Coprinus cinereus: Catalytic Promiscuity and Cyclization of Farnesyl Pyrophosphate Geometric Isomers
  作者：Fernando Lopez-Gallego、Sean A. Agger、Daniel Abate-Pella、Mark D. Distefano、Claudia Schmidt-Dannert

  DOI：10.1002/cbic.200900671

  日期：——

  Cyclization of FPP: Two new fungal sesquiterpene synthase are described that have opposite catalytic fidelities in the cyclization of farnesyl diphosphate. Catalytic promiscuity can be drastically reduced by changing the conditions of the reaction. Conversion of the FPP geometric isomers was found to proceed via opposite enantiomers of a cyclic carbocation intermediate that are rearranged to different

  FPP 的环化：描述了两种新的真菌倍半萜烯合酶，它们在二磷酸法呢酯的环化中具有相反的催化保真度。通过改变反应条件可以大大减少催化混杂。发现 FPP 几何异构体的转化是通过环状碳阳离子中间体的相反对映异构体进行的，这些对映异构体重新排列成不同的倍半萜烯产物。
• Epicubebol and Related Sesquiterpenoids from the Brown Alga<i>Dictyopteris divaricata</i>
  作者：Minoru Suzuki、Nobuhiko Kowata、Etsuro Kurosawa

  DOI：10.1246/bcsj.54.2366

  日期：1981.8

  Epicubebol has been isolated from the methanol extracts of the brown alga Dictyopteris divaricata as the major constituent. Cadinane-type sesquiterpenes, cubebenes, δ-cadinene, cubenol, and epicubenol, as well as two sesquiterpene methyl ethers as minor constituents have also been obtained from the extracts.

  从褐藻 Dictyopteris divaricata 的甲醇提取物中分离出的主要成分是表贝酚。此外，还从萃取物中获得了笛烷类倍半萜、立方烯、δ-笛烷烯、立方醇和表贝醇，以及作为次要成分的两种倍半萜甲基醚。
• A Multiproduct Terpene Synthase from <i>Medicago truncatula</i> Generates Cadalane Sesquiterpenes via Two Different Mechanisms
  作者：Stefan Garms、Tobias G. Köllner、Wilhelm Boland

  DOI：10.1021/jo100917c

  日期：2010.8.20

  Terpene synthases are responsible for a large diversity of terpene carbon skeletons found in nature. The multiproduct sesquiterpene synthase MtTPS5 isolated from Medicago truncatula produces 27 products from farnesyl diphosphate (1, FDP). In this paper, we report the reaction steps involved in the formation of these products using incubation experiments with deuterium-containing substrates; we determined

  萜烯合酶负责在自然界中发现的大量萜碳骨架。从梅花苜蓿分离的多产物倍半萜烯合酶MtTPS5从二磷酸法呢酯（1，FDP）产生27种产物。在本文中，我们报告了使用含氘底物的孵育实验形成这些产物所涉及的反应步骤。我们确定了各个产品的绝对构型，以建立反应级联​​的立体化学过程和循环底物的初始构象。用氘氧化进行的附加标记实验表明，卡达仑倍半萜主要是通过中性中间germ烯D的质子化产生的（5）。这些发现提供了另一途径，即通过神经磷酸二磷酸神经脂酯（2，NDP）进入具有金刚烷骨架的倍半萜的途径。对该酶的突变分析表明，酪氨酸残基对质子化过程很重要。
• Lessons from 1,3-Hydride Shifts in Sesquiterpene Cyclizations
  作者：Jan Rinkel、Patrick Rabe、Paolina Garbeva、Jeroen S. Dickschat

  DOI：10.1002/anie.201608042

  日期：2016.10.17

  initial 1,10‐cyclisation‐1,3‐hydride shift cascades. Enzymes with products of known absolute configuration showed a coherent stereochemical course, except for (−)‐α‐amorphene synthase, for which the obtained results are better explained by an initial 1,6‐cyclisation. The link between the absolute configuration of the product and the stereochemical course of the 1,3‐hydride shifts enabled assignment of

  用7种细菌倍半萜环化酶将立体标记的前体转化，以研究其最初的1,10-环化-1,3-氢化物移位级联反应的立体化学。带有已知绝对构型的产物的酶显示出连贯的立体化学过程，除了（-）-α-Amorphene合酶外，最初的1,6-环化可以更好地解释所获得的结果。产品的绝对构型与1,3-氢化物转变的立体化学过程之间的联系使得可以分配三种酶产物的绝对构型，这可以通过常见副产物胚芽戊二烯D-4-ol的绝对构型独立确认。
• Biomimetic transformations of germacradienes. Stereospecific conversion of hedycaryol phenyl sulfides to cadinanes
  作者：Mitsuaki Kodama、Karuaki Shimada、Toshiya Takahashi、Chizuko Kabuto、Shô Itô

  DOI：10.1016/s0040-4039(01)82930-0

  日期：1981.1

  E,E- and 2Z,6E-hedycaryol phenyl sulfides were converted by [2.3]sigmatropy of their sulfoxides to the same allyl alcohol which in turn afforded cadinane derivatives stereospecifically by the action of acids.

  通过[2.3]亚砜的亚砜将E，E-和2Z，6E-巯基苯酚苯基硫化物转化为相同的烯丙醇，该烯丙醇又通过酸的作用立体定向地提供了癸二烷衍生物。