threo-1,2-epoxy-3,7-dimethy-6-octen-3-ol | 29428-57-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: threo-1,2-epoxy-3,7-dimethy-6-octen-3-ol
• 英文别名: 1,2-epoxylinalool；(2R)-6-methyl-2-[(2S)-oxiran-2-yl]hept-5-en-2-ol
• CAS: 29428-57-7
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: BXOURKNXQXLKRK-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  threo-1,2-epoxy-3,7-dimethy-6-octen-3-ol 在 bis(acetylacetonate)oxovanadium 盐酸 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 正丁基锂 、 四甲基乙二胺 、 四丁基氟化铵 、 sodium 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 72.0h， 生成 (2R,5R)-tetrahydro-2-<(2S,5R)-tetrahydro-5-<(1S,4S,5R)-1,4,5-trihydroxy-1,5,9-trimethyldec-8-enyl>furan-2-yl>-5-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-2-methylfuran
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013
• 作为产物：
  描述：

  (R)-芳樟醇 在 bis(acetylacetonate)oxovanadium 、 叔丁基过氧化氢 作用下， 以 甲苯 、 癸烷 为溶剂， 反应 20.17h， 以30%的产率得到threo-1,2-epoxy-3,7-dimethy-6-octen-3-ol
  参考文献：
  名称：

  非对映体化环氧化和硒催化的氧化环化合成（+）-希腊烟草内酯

  摘要：

  从容易获得的（R）-芳樟醇开始发展C 11-杂环类（+）-希腊烟草内酯的不对称合成。该合成包括四个步骤，其特征在于使用钒，钯和硒催化的环化反应生成非对映体化环氧化和氧化四氢吡喃。

  DOI：

  10.1021/acs.orglett.7b00484

文献信息

• Synthesis of (R)- and (R)-4-methyl-6-2?-methylprop-1?-enyl-5,6-dihydro-2H-pyran (Nerol oxide) and Natural Occurrence of its Racemate
  作者：G�nther Ohloff、Wolfgang Giersch、Karl H. Schulte-Elte、Paul Enggist、Edouard Demole

  DOI：10.1002/hlca.19800630626

  日期：1980.9.17

  3-epoxy-citronellols (5) was prepared from (−)-(R)-linalool (3) via epoxy alcohol 4 and then reduced to (−)-(R)-3-hydroxy-citronellol (6). Sensitized photooxygenation of (−)-(R)-diol 6 led in part to (−)-(R)-triol 8 which was cyclodehydrated by dilute acid to a mixture of diastereoisomeric tetrahydropyran-4-ols 9 and 10. Dehydration of hydroxy ethers 9 and 10 afforded (−)-(S)-nerol oxide (11) and (+)-(R)-nerol

  按照已知方法，由（-）-制备（-）-（2 S，3 R）-和（+）-（2 R，3 R）-2,3-环氧香茅酚（5）的混合物。（R）-芳樟醇（3）通过环氧醇4，然后还原为（-）-（R）-3-羟基-香茅醇（6）。（-）-（R）-二醇6的敏化光氧化部分导致（-）-（R）-三醇8，后者被稀酸环化脱水成非对映异构体四氢吡喃-4-醇9和10的混合物。羟基醚9和10的脱水分别得到（-）-（S）-氧化新戊二醇（11）和（+）-（R）-氧化新戊二醇（12），光学纯度为91％。从保加利亚玫瑰油中分离出的氧化氮（0.038％）被证明是外消旋的。这些结果为植物中氧化神经醇的形成提供了一些启示。
• Total synthesis and biological evaluation of the natural product (−)-cyclonerodiol, a new inhibitor of IL-4 signaling
  作者：Jens Langhanki、Kristina Rudolph、Gerhard Erkel、Till Opatz

  DOI：10.1039/c4ob02021a

  日期：——

  In a screening program of natural compounds from fungi, the known cyclopentanoid sesquiterpene (−)-cyclonerodiol was identified as a specific inhibitor of the IL-4 induced STAT6 signaling pathway (IC50 = 9.7 μM) which is required for the differentiation of naive CD4 T cells to T helper type 2 (Th2) lymphocytes. As many allergic conditions, including allergic asthma and atopic diseases, are driven by

  在真菌天然化合物的筛选程序中，已知的环戊烷倍半萜（-）-环神经二醇被鉴定为IL-4诱导的STAT6信号通路的特异性抑制剂（IC 50 = 9.7μM），这是幼稚CD4分化所必需的T细胞至T辅助2型（Th2）淋巴细胞。由于过度的Th2反应导致许多过敏性疾病，包括过敏性哮喘和特应性疾病，因此STAT6是开发新疗法的有希望的目标。使用环氧自由基环化作为关键步骤，从（-）-芳樟醇分六步合成了该化合物。
• Synthesis of Plakortolides E and I Enabled by Base Metal Catalysis
  作者：Stefan Leisering、Alexandros Mavroskoufis、Patrick Voßnacker、Reinhold Zimmer、Mathias Christmann

  DOI：10.1021/acs.orglett.1c01457

  日期：2021.6.18

  A protecting-group-free synthesis of two endoperoxide natural products, plakortolide E and plakortolide I, is reported. Key steps are a vanadium-mediated epoxidation, an iron-catalyzed allylic substitution, and a cobalt-induced endoperoxide formation. Our approach combines chemoselective bond-forming reactions and one-pot operations to forge an overall efficient synthesis.

  报道了两种内过氧化物天然产物 plakortolide E 和 plakortolide I 的无保护基合成。关键步骤是钒介导的环氧化、铁催化的烯丙基取代和钴诱导的内过氧化物形成。我们的方法结合了化学选择性键形成反应和一锅法操作，以形成整体高效的合成。
• Regio- and stereocontrolled synthesis of epoxy alcohols and triols from allylic and homoallylic alcohols via iodocarbonates
  作者：Alessandro Bongini、Giuliana Cardillo、Mario Orena、Gianni Porzi、Sergio Sandri

  DOI：10.1021/jo00145a004

  日期：1982.11
• Protecting-Group-Free Synthesis of Chokols
  作者：Carmen Pérez Morales、Julieta Catalán、Victoriano Domingo、José A. González Delgado、José A. Dobado、M. Mar Herrador、José F. Quílez del Moral、Alejandro F. Barrero

  DOI：10.1021/jo102280n

  日期：2011.4.15

  As a result of a combined theoretical and experimental study, we describe a two-step protocol for the preparation of an optically pure, multifunctional, cyclopentanic core shared by a number of natural products. This process is based on a hitherto unreported Ti(III)-mediated diastereoselective cyclization in which the hydroxy-directed template effect played by the Ti(III) species was found to be crucial for the stereoselective outcome of the reaction. The viability of this concept was confirmed with the first protecting-group free synthesis of three enantiopure chokols, namely, chokols K, E, and B.