(±)-(3S,4S)-3,4-epoxy-1-undecene | 88086-60-6

• 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: (±)-(3S,4S)-3,4-epoxy-1-undecene
• 英文别名: trans-3,4-epoxy-1-undecene；(2S,3S)-2-ethenyl-3-heptyloxirane
• CAS: 88086-60-6；88086-62-8；98441-86-2
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: AFJNBWVDBYUPQJ-QWRGUYRKSA-N

物化性质

• 沸点：
  227.0±9.0 °C(Predicted)
• 密度：
  0.908±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  7
• 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：

  (±)-(3S,4S)-3,4-epoxy-1-undecene 在 六氟乙酰丙酮化铜的水合物 碳酸氢钠 、 硫脲 作用下， 以 甲醇 、 苯 为溶剂， 反应 18.0h， 生成 2-heptyl-2,5-dihydrothiophene
  参考文献：
  名称：

  Highly Selective Copper-Catalyzed Ring Expansion of Vinyl Thiiranes:  Application to Synthesis of Biotin and the Heterocyclic Core of Plavix

  摘要：

  We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described.

  DOI：

  10.1021/ja069059h
• 作为产物：
  描述：

  (E)-undeca-1,3-diene 在 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以30%的产率得到(±)-(3S,4S)-3,4-epoxy-1-undecene
  参考文献：
  名称：

  Copper-Catalyzed Rearrangement of Vinyl Oxiranes

  摘要：

  A novel copper-catalyzed vinyl oxirane ring expansion protocol has been developed. A wide range of vinyl oxiranes can be rearranged to 2,5-dihydrofurans in excellent yields in the presence of electrophilic copper(II) acetylacetonate catalysts. Regioisomeric vinyl oxiranes can be converted to a single dihydrofuran product using these conditions. This method uses low catalyst loadings (0.5-5 mol %), has good tolerance of substitution patterns, and can be done in the absence of solvent.

  DOI：

  10.1021/ja067073o

文献信息

• A Synthesis of the Chlorosulfolipid Mytilipin A via a Longest Linear Sequence of Seven Steps
  作者：Won-jin Chung、Joseph S. Carlson、D. Karl Bedke、Christopher D. Vanderwal

  DOI：10.1002/anie.201304565

  日期：2013.9.16

  Magnificent seven: The chlorosulfolipid mytilipin A was synthesized in racemic form in seven steps and in enantioenriched form in eight steps. Key transformations include a highly diastereoselective bromoallylation of a sensitive α,β‐dichloroaldehyde, a kinetic resolution of a vinyl epoxide, a convergent and highly Z‐selective alkene cross‐metathesis, and a chemoselective and diastereoselective dichlorination

  精彩七：氯硫脂 mytilipin A 以外消旋形式分七步合成，对映体富集形式分八步合成。关键转化包括敏感的 α,β-二氯醛的高度非对映选择性溴烯丙基化、乙烯基环氧化物的动力学拆分、会聚和高度Z选择性烯烃交叉复分解，以及复合二烯的化学选择性和非对映选择性二氯化。
• A simple, stereoselective, room-temperature synthesis of cis vinyloxiranes and trans 1-phenyl-1,3-butadiene
  作者：Jacques Auge、Serge David

  DOI：10.1016/s0040-4039(00)88249-0

  日期：1983.1

  The organotin reagent from 1-chloro-3-iodoprop-1-ene and SnCl2 in dimethylformamide reacted with aldehydes by ite chlorine-substituted carbon atom. Treatment with NaOMe then gave vinyloxiranes with good stereo-selectivity. benzaldehyde and 1-bromo-3-iodoprop-1-ene in the presence of two equivalents of SnCl2 gave exclusively -1-phenyl-1,3-butadiene.

  1-氯-3-碘丙-1-烯和SnCl 2在二甲基甲酰胺中的有机锡试剂通过氯取代的碳原子与醛反应。然后用NaOMe处理得到具有良好立体选择性的乙烯基环氧乙烷。在两当量的SnCl 2存在下，苯甲醛和1-溴-3-碘丙-1-烯仅产生-1-苯基-1,3-丁二烯。
• Production of 2,5-Dihydrofurans and Analogous Compounds
  申请人：Njardarson Jon

  公开号：US20090131691A1

  公开（公告）日：2009-05-21

  Vinyl oxiranes are rearranged to 2,5-dihydrofuran using catalyst (III) or (IV). The 2,5-dihydrofuran can be reduced to tetrahydrofuran. 3,4-Epoxy-1-butene substrate is converted to 2,5-dihydrofuran which in turn is converted to tetrahydrofuran. Substrate for making 3-methyltetrahydrofuran is prepared from isoprene. Substrate for making 2-methyltetrahydrofuran is prepared from piperylene. Reactions analogous to that with vinyl oxiranes are carried out with vinyl thiiranes and vinyl aziridines.

  乙烯基环氧烷通过催化剂（III）或（IV）重排成2,5-二氢呋喃。2,5-二氢呋喃可以还原成四氢呋喃。3,4-环氧-1-丁烯底物被转化为2,5-二氢呋喃，然后转化为四氢呋喃。制备3-甲基四氢呋喃的底物来自异戊二烯。制备2-甲基四氢呋喃的底物来自戊二烯。与乙烯基环氧硫烷和乙烯基氮杂环丙烷类似的反应也可以进行。
• WO2007/108999
  申请人：——

  公开号：——

  公开（公告）日：——
• US8404872B2
  申请人：——

  公开号：US8404872B2

  公开（公告）日：2013-03-26