噁丙环,2-[(苯基甲氧基)甲基]-3-丙基-,(2R,3S)-rel- | 107076-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 噁丙环,2-[(苯基甲氧基)甲基]-3-丙基-,(2R,3S)-rel-
• 英文名称: (E)-1-(benzyloxy)-2,3-epoxyhexane
• 英文别名: (2S,3S)-2-(phenylmethoxymethyl)-3-propyloxirane
• CAS: 107076-91-5；116949-66-7；145032-21-9；146388-80-9
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: NFQNKIPOHHGDFH-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  噁丙环,2-[(苯基甲氧基)甲基]-3-丙基-,(2R,3S)-rel- 在 magnesium iodide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 6.0h， 以90%的产率得到(2S^*,3R^*)-1-(Benzyloxy)-3-iodohexan-2-ol
  参考文献：
  名称：

  Regioselective opening of epoxy alcohols: mild chemo- and stereoselective preparation of iodohydrins and 1,2-diols

  摘要：

  Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.

  DOI：

  10.1021/jo00021a045
• 作为产物：
  描述：

  (E)-((hex-2-en-1-yloxy)methyl)benzene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以91%的产率得到噁丙环,2-[(苯基甲氧基)甲基]-3-丙基-,(2R,3S)-rel-
  参考文献：
  名称：

  Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 5. Synthesis and reactions of some 2,3-epoxy-1-alkanol derivatives

  摘要：

  In order to study the effect of a remote polar functionality on the regiochemistry of the ring opening of aliphatic epoxides, the synthesis and some nucleophilic additions (methanolysis, azidolysis, and aminolysis) of suitable 2,3-epoxy-1-alkanol derivatives (epoxides trans-1a-d and cis-2) were carried out. The C-3 selectivity commonly observed when nonchelating ring opening conditions are used is lower than when the epoxides are allowed to react in the presence of metal ions (Li+, Mg2+, Zn2+) due to the probable intervention of bidentate-chelated intermediates in the latter case, and in some instances an almost complete C-3 regioselection is obtained. Under identical conditions involving chelation control, trans epoxide la shows higher C-3 selectivity than cis isomer 2. A free hydroxyl functionality is not necessary in order to observe chelation-controlled regioselectivity in the epoxides that we examined.

  DOI：

  10.1021/jo00057a040

文献信息

• Arabinose-Derived Ketones as Catalysts for Asymmetric Epoxidation of Alkenes
  作者：Tony K. M. Shing、Gulice Y. C. Leung、To Luk

  DOI：10.1021/jo050928f

  日期：2005.9.1

  Readily available arabinose-derived ketones, containing a tunable butane-2,3-diacetal as the steric blocker, displayed increasing enantioselectivity (up to 90% ee) with the size of the acetal alkyl group in catalytic asymmetric epoxidation of trans-disubstituted and trisubstituted alkenes. The stereochemical communication between our ketone catalysts and the alkene substrates is mainly due to steric

  现成的阿拉伯糖衍生的酮，包含可调节的2,3-丁烷作为空间阻滞剂，在反式-二取代和三取代的催化不对称环氧化反应中，随着乙缩醛烷基大小的增加，对映选择性增加（最多90％ee）。烯烃。我们的酮催化剂与烯烃底物之间的立体化学连通主要是由于空间效应，而涉及底物和催化剂的苯基之间的π-π相互作用的电子效应在我们的系统中似乎不起作用。
• Regio and diastereoselective oxygen assisted opening by mono-chloroborane-dimethylsulfide of epoxides to anti Chlorohydrins.
  作者：Paolo Bovicelli、Paolo Lupattelli、Maria Teresa Bersani、Enrico Mincione

  DOI：10.1016/s0040-4039(00)60037-0

  日期：1992.10

  The opening reaction of epoxides by monochloroborane-dimethylsulfide 1 proceeds by oxygen anchimeric assistance in a regio and diastereoselective manner to give the corresponding anti chlorohydrins.

  通过一氯硼烷-二甲基硫醚1的环氧化物的开环反应通过氧骨架异构反应以区域和非对映选择性的方式进行，得到相应的抗氯代醇。
• A new base promoted rearrangement of (E)-1-benzyloxy-2,3-epoxyalkanes
  作者：Angelika Thurner、Ferenc Faigl、Alessandro Mordini、Anna Bigi、Gianna Reginato、László Töke

  DOI：10.1016/s0040-4020(98)00684-x

  日期：1998.9

  (E)-1-benzyloxy-2,3-epoxyalkanes (4) underwent stereoselective rearrangement in the presence of LIDAKOR reagent and large excess of butyllithium producing (Z)-alkendiols (7) at ambident temperature. The same reaction serves anti oxetanes (6) at −75 °C which can also rearrange to 7 when the temperature arises.

  （ê）-1-苄氧基-2,3-环氧烷烃（4）行立体选择性重排LIDAKOR试剂和大量过量的丁基锂制备（的存在Ž在两可温度）-alkendiols（7）。相同的反应在-75°C时产生抗氧杂环丁烷（6），当温度升高时也可以重排至7。
• Useful base promoted elaborations of oxiranyl ethers
  作者：Angelika Thurner、Ferenc Faigl、László Tőke、Alessandro Mordini、Michela Valacchi、Gianna Reginato、Gábor Czira

  DOI：10.1016/s0040-4020(01)00790-6

  日期：2001.9

  Functionalized oxiranyl ethers can be regio- and stereoselectively converted into hydroxy oxetanes or cis-diols by treatment with organometallic bases. These two rearrangements can be conveniently carried out either using different reaction conditions starting from the oxirane or in two consecutive steps from the oxirane via the oxetane. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 18: Regioselectivity of the opening reactions with MeOH of 1-(benzyloxy)-2,3- and -3,4-epoxyalkanes under condensed and gas phase operating conditions
  作者：Paolo Crotti、Gabriele Renzi、Graziella Roselli、Valeria Di Bussolo、Laura Lucarelli、Maria Rosaria Romano

  DOI：10.1016/j.tet.2005.05.040

  日期：2005.8

  The regiochemical behavior of a series of aliphatic open chain epoxides bearing a heterofunctionality in an allylic or homoallylic relationship has been examined in the opening reaction with MeOH under both condensed and gas phase operating conditions. The results indicate that the proton (actually D+) possesses in the gas phase intrinsic chelating properties which are even superior than those of Li (+) in the condensed phase. (c) 2005 Elsevier Ltd. All rights reserved.