(R)-2-(non-8-enyl)oxirane | 866415-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (R)-2-(non-8-enyl)oxirane
• 英文别名: (2R)-2-non-8-enyloxirane
• CAS: 866415-99-8
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: BUCRBRBWIKDPPZ-LLVKDONJSA-N

物化性质

• 沸点：
  220.5±9.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-(non-8-enyl)oxirane 在 lithium aluminium tetrahydride 作用下， 以90%的产率得到(S)-undec-10-en-2-ol
  参考文献：
  名称：

  （+）-aspicilin的立体选择性全合成

  摘要：

  描述了（+）-aspicilin的立体选择性合成。分子内参与亚磺酰基的区域和立体选择性功能化，烯键反应以及采用Masamune-Roush方案通过Wadsworth-Emmons反应进行大内酰胺化是该路线的关键步骤。

  DOI：

  10.1016/j.tetlet.2006.05.043
• 作为产物：
  描述：

  10-十一烯醛 在 sodium tetrahydroborate 、 sodium persulfate 、 (2S,5R)-5-methyl-2-tert-butyl-3-methylimidazolidin-4-one hydrochloride 、 copper(II) trifluoroacetate 、 lithium chloride 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 8.5h， 生成 (R)-2-(non-8-enyl)oxirane
  参考文献：
  名称：

  Resorcylic Acid Lactone Biosynthesis Relies on a Stereotolerant Macrocyclizing Thioesterase

  摘要：

  Zearalenone and radicicol are highly related resorcylic acid lactones with the rare property of having opposite stereochemical configurations of the secondary alcohol involved in lactone formation. The ability of the thioesterases from the zearalenone and radicicol biosynthetic pathways to macrocyclize both d and l configured synthetic substrate analogs was biochemically characterized and showed that both enzymes were highly stereotolerant, macrocyclizing both substrates with similar kinetic parameters. This observed stereotolerance is consistent with a proposed evolution of both natural products from a common ancestral resorcylic acid lactone.

  DOI：

  10.1021/ol502747t

文献信息

• Enantioselective Linchpin Catalysis by SOMO Catalysis: An Approach to the Asymmetric α-Chlorination of Aldehydes and Terminal Epoxide Formation
  作者：Muriel Amatore、Teresa D. Beeson、Sean P. Brown、David W. C. MacMillan

  DOI：10.1002/anie.200901855

  日期：2009.6.29

  Time for SOme MOre: For the first time SOMO (singly occupied molecular orbital) activation has been exploited to allow a new approach to the α‐chlorination of aldehydes. This transformation can be readily implemented as part of a linchpin catalysis approach to the enantioselective production of terminal epoxides.

  SOme MOre 时间：首次利用 SOMO（单占据分子轨道）激活来实现醛的 α-氯化的新方法。这种转化可以很容易地作为对映选择性生产末端环氧化物的关键催化方法的一部分来实现。
• Stereoselective total synthesis of (+)-aspicilin
  作者：Sadagopan Raghavan、T. Sreekanth

  DOI：10.1016/j.tetlet.2006.05.043

  日期：2006.7

  A stereoselective synthesis of (+)-aspicilin is described. Regio- and stereoselective functionalization by intramolecular participation of the sulfinyl group, ene reaction, and macrolactonization by Wadsworth–Emmons reaction employing Masamune–Roush protocol are the key steps of the route.

  描述了（+）-aspicilin的立体选择性合成。分子内参与亚磺酰基的区域和立体选择性功能化，烯键反应以及采用Masamune-Roush方案通过Wadsworth-Emmons反应进行大内酰胺化是该路线的关键步骤。
• Stereochemistry of Endogenous Palmitic Acid Ester of 9-Hydroxystearic Acid and Relevance of Absolute Configuration to Regulation
  作者：Andrew T. Nelson、Matthew J. Kolar、Qian Chu、Ismail Syed、Barbara B. Kahn、Alan Saghatelian、Dionicio Siegel

  DOI：10.1021/jacs.7b01269

  日期：2017.4.5

  elucidating the roles of these lipids, but these studies were performed with racemic mixtures, and the role of stereochemistry remains unexplored. Here, we synthesized the R- and S- palmitic acid ester of 9-hydroxystearic acid (R-9-PAHSA, S-9-PAHSA). Access to highly enantioenriched PAHSAs enabled the development of a liquid chromatography-mass spectrometry (LC-MS) method to separate and quantify R- and S-9-PAHSA

  脂质在细胞和生物体的结构、能量学和信号传导中具有基本作用。最近发现的羟基脂肪酸脂肪酸酯 (FAHFA) 是一种具有强效抗糖尿病和抗炎活性的脂质，表明我们对脂质组的组成和脂质功能的理解是不完整的。合成和测试 FAHFA 的能力对于阐明这些脂质的作用至关重要，但这些研究是用外消旋混合物进行的，立体化学的作用仍未得到探索。在这里，我们合成了 9-羟基硬脂酸的 R-和 S-棕榈酸酯（R-9-PAHSA、S-9-PAHSA）。获得高度对映体富集的 PAHSA 促进了液相色谱-质谱 (LC-MS) 方法的开发，以分离和量化 R-和 S-9-PAHSA，这种方法确定 R-9-PAHSA 是主要的立体异构体，它在 FAHFA 首次被发现的转基因小鼠的脂肪组织中积累。此外，9-PAHSA 生物合成和降解的生化分析表明 PAHSA 产生的酶和途径是立体特异性的，细胞系有利于 R-9-PAHSA 和羧基酯脂肪酶
• Stereoselective synthesis of (−)-jimenezin
  作者：Cheol Hee Hwang、Gyochang Keum、Kyoung Il Sohn、Dong Hoon Lee、Eun Lee

  DOI：10.1016/j.tetlet.2005.07.148

  日期：2005.9

  Total synthesis of jimenezin was achieved via radical cyclization of beta-alkoxyacrylate and beta-alkoxyvinyl sulfoxide intermediates and intramolecular olefin metathesis reaction. (c) 2005 Published by Elsevier Ltd.
• Resorcylic Acid Lactone Biosynthesis Relies on a Stereotolerant Macrocyclizing Thioesterase
  作者：Graham W. Heberlig、Monica Wirz、Meng Wang、Christopher N. Boddy

  DOI：10.1021/ol502747t

  日期：2014.11.21

  Zearalenone and radicicol are highly related resorcylic acid lactones with the rare property of having opposite stereochemical configurations of the secondary alcohol involved in lactone formation. The ability of the thioesterases from the zearalenone and radicicol biosynthetic pathways to macrocyclize both d and l configured synthetic substrate analogs was biochemically characterized and showed that both enzymes were highly stereotolerant, macrocyclizing both substrates with similar kinetic parameters. This observed stereotolerance is consistent with a proposed evolution of both natural products from a common ancestral resorcylic acid lactone.