(R)-non-8-en-2-ol | 211695-57-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-non-8-en-2-ol
• 英文别名: (2R)-non-8-en-2-ol
• CAS: 211695-57-7
• 化学式: C₉H₁₈O
• 分子量: 142.241
• InChiKey: VMDNDMBRUXRQCH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-non-8-en-2-ol 在 咪唑 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三氟甲磺酸三甲基硅酯 、 氢氟酸 、 水 、 对苯醌 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.67h， 生成 (R,E)-9-(((2R,3R,5R,6S)-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)dec-2-enoic acid
  参考文献：
  名称：

  Deep Interrogation of Metabolism Using a Pathway-Targeted Click-Chemistry Approach

  摘要：

  Untargeted metabolomics indicates that the number of unidentified small-molecule metabolites may exceed the number of protein-coding genes for many organisms, including humans, by orders of magnitude. Uncovering the underlying metabolic networks is essential for elucidating the physiological and ecological significance of these biogenic small molecules. Here we develop a click-chemistry-based enrichment strategy, DIMEN (deep interrogation of metabolism via enrichment), that we apply to investigate metabolism of the ascarosides, a family of signaling molecules in the model organism C. elegans. Using a single alkyne modified metabolite and a solid-phase azide resin that installs a diagnostic moiety for MS/MS-based identification, DIMEN uncovered several hundred novel compounds originating from diverse biosynthetic transformations that reveal unexpected intersection with amino acid, carbohydrate, and energy metabolism. Many of the newly discovered transformations could not be identified or detected by conventional LC-MS analyses without enrichment, demonstrating the utility of DIMEN for deeply probing biochemical networks that generate extensive yet uncharacterized structure space.

  DOI：

  10.1021/jacs.0c06877
• 作为产物：
  描述：

  壬-8-烯-2-醇 在 Novozym 435 lipase 、 potassium hydroxide 作用下， 以 甲醇 、 异丙醚 为溶剂， 反应 4.5h， 生成 (R)-non-8-en-2-ol
  参考文献：
  名称：

  大病毒素A的组成型C 22-羧酸的不对称合成

  摘要：

  已经开发出大病毒素A的C 22-三羟基脂肪酸组分的有效不对称合成。关键步骤是高度对映选择性（i）脂肪酶催化的酰化作用；（ii）InCl 3-（S）-BINOL介导的烯丙基化作用；以及（iii）不对称二羟基化（ADH）反应。通过将所得的二醇非对映异构体转化为所需的环氧对映体，可以克服ADH反应的中等非对映选择性。

  DOI：

  10.1016/j.tet.2015.01.010

文献信息

• Stereochemical Assignment of the Fungal Metabolites Pestalotiopsones D and E through Enantiopure Synthesis
  作者：Andrew Michael Beekman、Russell Allan Barrow

  DOI：10.1021/np400473u

  日期：2013.11.22

  of pestalotiopsones D (4) and E (5) were elucidated through total synthesis of both the R and S enantiomers, allowing for the assignment of the stereochemistry of the natural compounds as the (+)-S enantiomers. The key steps include homologation of a substituted benzoic acid to the appropriate phenylacetate derivative using Birch reductive alkylation, an oxa-Michael cyclization induced by microwave irradiation

  瘟疫调理素是从内生真菌Pestalotiopsis sp。分离的真菌代谢产物。发现于红树林Rhizophora mucronata中，用于中药治疗痢疾的症状。通过完全合成R和S对映异构体，阐明了鼠疫调理素D（4）和E（5）的绝对构型，从而可以将天然化合物的立体化学指定为（+）- S对映体。关键步骤包括使用Birch还原烷基化将取代的苯甲酸同化为适当的苯乙酸酯衍生物，通过微波辐射诱导形成苯并二氢吡喃酮亚基的oxa-Michael环化反应以及由IBX介导的脱氢反应生成苯并酮骨架。进行了针对临床病原体的合成化合物的评估。
• Syntheses of Cytosporones A, C, J, K, and N, Metabolites from Medicinal Fungi
  作者：Andrew M. Beekman、Russell A. Barrow

  DOI：10.1071/ch15144

  日期：——

  compounds for the first time. The key steps included a recently described homologation of benzoic acid to the analogous phenyl acetate using Birch reductive alkylation conditions, acylation of the appropriate phenyl acetate derivative, and a selective reduction and spontaneous biomimetic lactonization to yield the 3-isochromanone skeleton. The synthesized natural products were evaluated for their biological

  报道了真菌代谢产物细胞孢子A，（±）-C和N的合成。并首次描述了细胞孢子J和K的合成。含有稀有的3-异苯并二氢吡喃酮亚结构的天然产物外消旋细胞孢子J和外消旋细胞孢子K的制备分别以8个线性步骤进行，总产率分别为45％和7个线性步骤，产率为46％，从而完成了表征这些化合物是第一次。关键步骤包括最近描述的使用桦木还原烷基化条件将苯甲酸同化为乙酸苯酯的类似物，适当乙酸苯酯衍生物的酰化，以及选择性还原和自发仿生内酯化以生成3-isochromanone骨架。
• Novel Carboxylic Acid and Antidepressant Composition Containing the Same as Active Ingredient
  申请人：Yoshimura Hiroyuki

  公开号：US20100184860A1

  公开（公告）日：2010-07-22

  The present invention provides a novel compound and antidepressant composition that can be effectively used for improving depressed mood and depressed state, particularly for depressed mood and depressed state in menopausal women. The compound of the present invention is represented by the following formula (1): wherein R 1 and R 2 are identical or different and represent a hydrogen atom, a hydroxyl group or an acetyloxy group, and n is an integer of 2 to 7, or a pharmaceutically acceptable salt or ester thereof. This compound is used as an active ingredient in the antidepressant composition. Examples of the compound of the invention include (2E)-9,10-dihydroxy-2-decenoic acid, (2Z)-9,10-dihydroxy-2-decenoic acid, (2E)-9-hydroxy-2-decenoic acid, and (2E)-7-acetoxy-2-heptenoic acid.

  本发明提供了一种新型化合物和抗抑郁剂组合物，可有效用于改善抑郁情绪和抑郁状态，特别是用于绝经期妇女的抑郁情绪和抑郁状态。本发明的化合物由以下式（1）表示：其中R1和R2相同或不同，代表氢原子、羟基或乙酰氧基，n为2至7的整数，或其药学上可接受的盐或酯。该化合物作为抗抑郁剂组合物中的活性成分使用。本发明的化合物示例包括（2E）-9,10-二羟基-2-癸烯酸，（2Z）-9,10-二羟基-2-癸烯酸，（2E）-9-羟基-2-癸烯酸和（2E）-7-乙酰氧基-2-庚烯酸。
• Total synthesis of greensporone C
  作者：Kwanruthai Tadpetch、Laksamee Jeanmard、Vatcharin Rukachaisirikul

  DOI：10.1016/j.tetlet.2017.07.074

  日期：2017.8

  The first total synthesis of greensporone C, a cytotoxic 14-membered resorcylic acid lactone, has been accomplished via a longest linear sequence of 16 steps in 3.3% overall yield. The key features of the synthesis include Mitsunobu esterification and ring-closing metathesis to construct the macrocycle and establish the (E)-olefin geometry, respectively. Our synthesis also confirmed the absolute stereochemistry

  Greensporone C（一种具有细胞毒性的14元间苯二酸内酯）的首次总合成已通过16个步骤的最长线性序列完成，总产率为3.3％。合成的关键特征包括Mitsunobu酯化和闭环易位，以分别构建大环并建立（E）-烯烃的几何形状。我们的合成也证实了天然产物的绝对立体化学。
• Glycal approach to the synthesis of macrolide (−)-A26771B
  作者：Puli Saidhareddy、Arun K. Shaw

  DOI：10.1039/c4ra17084a

  日期：——

  A convergent total synthesis of a 16-membered macrolactone natural product (−)-A26771B 1 starting from 3,4,6-tri-O-acetyl-D-glucal 7 is reported. The Ferrier rearrangement of acetylated glucal 7, cross metathesis between chiral fragments 3 and 4, Yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.

  据报道，从3,4,6-三-O-乙酰基-D-葡糖醛7开始，由16个成员组成的大内酯天然产物（-）-A26771B 1会聚在一起。乙酰化葡聚糖7的Ferrier重排，手性片段3和4之间的交叉易位，山口大内酯化和烯丙醇的选择性氧化是合成的关键特征。