trans-2,3-epoxyoctane | 152441-84-4

• 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: trans-2,3-epoxyoctane
• 英文别名: (2R,3R)-2-methyl-3-pentyloxirane
• CAS: 152441-84-4
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: SNAUWGUVQBOHMZ-HTQZYQBOSA-N

物化性质

• 沸点：
  153.8±8.0 °C(Predicted)
• 密度：
  0.847±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  Titanocene dichloride 、 trans-2,3-epoxyoctane 生成 反-2-辛烯
  参考文献：
  名称：

  SCHOBERT, RAINER, ANGEW. CHEM., 100,(1988) N, C. 869-871

  摘要：

  DOI：
• 作为产物：
  描述：

  反-2-辛烯 在 [Ni^II(dpap)](ClO₄) 、 间氯过氧苯甲酸 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以72.1%的产率得到trans-2,3-epoxyoctane
  参考文献：
  名称：

  二级配位球中的质子开关，以控制金属中心的催化事件：mid酰胺镍配合物的仿生羰基转移化学

  摘要：

  高价金属氧物种是许多金属酶催化循环中氧原子转移步骤的关键中间体。尽管此类酶的氧化还原活性金属中心通常由阴离子氨基酸侧链或卟啉环支撑，但肽主链可能充当强电子给体配体，以稳定高氧化态。为了测试这种想法在合成环境中的可行性，我们准备了一种新的酰胺基多齿配体的镍（II）配合物。该N5配体的单核镍配合物通过使用mCPBA作为末端氧化剂来催化多种烯烃的环氧化反应。值得注意的是，对于末端烯烃底物观察到非常高的催化效率和选择性。我们发现，次级配位球的质子化是催化循环的入口，在催化循环中，随后形成高价镍物种进行氧转移反应。概念上平行的过程可能允许金属酶通过在次级配位领域使用质子开关来控制初级配位领域的催化循环。

  DOI：

  10.1002/chem.202005183

文献信息

• Titanium<i>cis</i>-1,2-Diaminocyclohexane (<i>cis</i>-DACH) Salalen Catalysts for the Asymmetric Epoxidation of Terminal Non-Conjugated Olefins with Hydrogen Peroxide
  作者：Qifang Wang、Jörg-M. Neudörfl、Albrecht Berkessel

  DOI：10.1002/chem.201404639

  日期：2015.1.2

  Chiral Ti salalen complexes catalyze the asymmetric epoxidation of terminal non‐conjugated olefins with hydrogen peroxide. Modular ligands based on cis‐1,2‐diamino‐cyclohexane (cis‐DACH) were developed, giving high yields and enantiomeric excesses (ee, up to 96 %) at catalyst loadings as low as 0.1–0.5 mol %, and even under solvent‐free conditions.

  手性Ti Salalen配合物催化过氧化氢催化末端非共轭烯烃的不对称环氧化。开发了基于顺式1,2-二氨基环己烷（cis - DACH）的模块化配体，在催化剂负载量低至0.1-0.5 mol％甚至更低的情况下，可提供高收率和对映体过量（ee，高达96％）无溶剂条件。
• Chemoenzymatic synthesis of “α-bichiral” synthons. Application to the preparation of chiral epoxides
  作者：Pascale Besse、Henri Veschambre

  DOI：10.1016/s0957-4166(00)80239-6

  日期：1993.6

  Microbiological reduction of 3-bromo-2-octanone and 3-azido-2-octanone led to all the stereoisomers of 3-bromo-2-octanol and 3-azido-2-octanol. Chiral 2,3-epoxyoctanes were prepared from the 3-bromo-2-octanols.
• Kinetic resolution of racemic halohydrins, precursors of optically active di- and trialkyl-substituted epoxides, with lipase from Pseudomonas sp.
  作者：Waldemar Adam、Lluís Blancafort、Chantu R. Saha-Möller

  DOI：10.1016/s0957-4166(97)00430-8

  日期：1997.10

  Asymmetric acetylation of racemic halohydrins with vinyl acetate catalyzed by lipase from Pseudomonas sp. afforded the optically active beta-halo alcohols 1 and acetates 2 in high enantiomeric excess (68 to > 98%). The enzymatic kinetic resolution was performed on the preparative scale and the halo alcohols 1 and acetates 2 led to the optically active epoxides 3 after base treatment. (C) 1997 Elsevier Science Ltd.
• Microbiological transformations. Part 39: Determination of the regioselectivity occurring during oxirane ring opening by epoxide hydrolases: a theoretical analysis and a new method for its determination
  作者：Philippe Moussou、Alain Archelas、Jacques Baratti、Roland Furstoss

  DOI：10.1016/s0957-4166(98)00122-0

  日期：1998.5

  In the course of this work we have devised new equations as well as a new method allowing for the total determination of the regioselectivity occurring during biohydrolysis of a racemic epoxide by an epoxide hydrolase. This determination is achievable by simply studying the racemic epoxide as a substrate. The results showed that, depending on the enantioselectivity (E value) and the regioselectivity involved, the absolute configuration as well as the enantiopurity of the residual epoxide and of the formed diol appear to be highly variable. For a specific enzyme/substrate couple, the yield and enantiopurity of the less reactive (remaining) epoxide-and thus the possibility to prepare it in enantiopure form-exclusively depend upon the enzyme enantioselectivity. On the other hand, the ee of the formed diol (eep) depends upon the enantioselectivity and on the regioselectivity of the oxirane ring opening. A theoretical analysis based on the material balance, as well as several practical examples, are provided to illustrate the various possibilities of such biohydrolyses. (C) 1998 Elsevier Science Ltd. All rights reserved.
• DENIS J. N.; VICENS J.; KRIEF A., TETRAHEDRON LETT., 1979, NO 29, 2697-2700
  作者：DENIS J. N.、 VICENS J.、 KRIEF A.

  DOI：——

  日期：——