癸烷-1,4-二醇 | 37810-94-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 癸烷-1,4-二醇
• 英文名称: 1,4-decanediol
• 英文别名: decane-1,4-diol；decan-1,4-diol；(+/-)-1,4-Decandiol
• CAS: 37810-94-9
• 化学式: C₁₀H₂₂O₂
• 分子量: 174.283
• InChiKey: GFICPCFLWFXIJC-UHFFFAOYSA-N

物化性质

• 熔点：
  28°C
• 沸点：
  263.09°C (rough estimate)
• 密度：
  0.9418 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  癸烷-1,4-二醇 在 pyridinium chlorochromate 作用下， 生成 4-oxodecanal
  参考文献：
  名称：

  Synthesis and Occurrence of Oxoaldehydes in Used Frying Oils

  摘要：

  As part of our efforts to identify volatile decomposition products in used frying oils, a series of 4- and 5-oxoaldehydes were synthesized, purified, and characterized by gas chromatography, gas chromatography-mass spectrometry, gas chromatography-Fourier transform infrared spectrometry, and nuclear magnetic resonance spectrometry. Oxoaldehydes have been proposed as possible precursors of alkylfurans, which have potential anticancer effects. In a model reaction 4-oxononanal was refluxed in hexane for 40 days and only trace amounts of 2-pentylfuran were produced, suggesting that it is not a major precursor of the furan. The volatile constituents of used frying oils obtained from commercial food processors were studied, and 4-oxohexanal, 4-oxooctanal, 4-oxononanal, and 4-oxodecanal were identified.

  DOI：

  10.1021/jf00049a006
• 作为产物：
  描述：

  1,4-dihydroxydec-2-yne 在 乙醇 、 镍 作用下， 生成 癸烷-1,4-二醇
  参考文献：
  名称：

  Gouge, Annales de Chimie (Cachan, France), 1951, vol. <12> 6, p. 648,682

  摘要：

  DOI：

文献信息

• Biocatalytic oxidation of 1,4-diols and γ-lactols into γ-lactones: application to chemoenzymatic synthesis of drospirenone
  作者：Diego Romano、Martina Contente、Tiziana Granato、William Remelli、Paolo Zambelli、Francesco Molinari

  DOI：10.1007/s00706-012-0921-3

  日期：2013.5

  4-butanediols with Acetobacter aceti MIM 2000/28 gave the corresponding γ-lactones in good yields. The biotransformation occurred with intermediate formation of γ-lactols, which are also substrates for oxidation with Acetobacter aceti MIM 2000/28, as validated by selective biotransformation of 6β,7β;15β,16β-dimethylene-3-oxo-17α-pregn-4-en-21,17-carbolactol to drospirenone. Graphical Abstract

  摘要用醋醋醋杆菌MIM 2000/28氧化1-烷基-1,4-丁二醇可得到相应的γ-内酯，收率很高。生物转化发生与中间形成γ -lactols，其也用于与氧化的衬底醋化醋杆菌MIM28分之2000，通过6的选择性生物转化为验证β，7 β ; 15 β，16 β二亚甲基-3-氧代-17- α -pregn-4-en-21,17-甲内酯为屈螺烯酮。 图形概要
• CYP505E3: A Novel Self‐Sufficient ω‐7 In‐Chain Hydroxylase
  作者：Mpeyake Jacob Maseme、Alizé Pennec、Jacqueline Marwijk、Diederik Johannes Opperman、Martha Sophia Smit

  DOI：10.1002/anie.202001055

  日期：2020.6.22

  The self‐sufficient cytochrome P450 monooxygenase CYP505E3 from Aspergillus terreus catalyzes the regioselective in‐chain hydroxylation of alkanes, fatty alcohols, and fatty acids at the ω‐7 position. It is the first reported P450 to give regioselective in‐chain ω‐7 hydroxylation of C10–C16 n ‐alkanes, thereby enabling the one step biocatalytic synthesis of rare alcohols such as 5‐dodecanol and 7‐tetradecanol

  来自土曲霉的自给自足的细胞色素P450单加氧酶CYP505E3催化ω-7位烷烃，脂肪醇和脂肪酸的区域选择性链内羟化反应。这是第一个报道的P450，具有C10–C16 n的区域选择性链内ω-7羟基化作用链烷烃，从而一步一步生物催化合成稀有醇（如5-十二烷醇和7-十四烷醇）。它显示出一个甲基末端对第八个碳原子的区域选择性超过70％，并且对癸烷（TTN≈8000）和十二烷（TTN≈2000）的活性很高。CYP505E3可用于通过两种途径合成高价值风味化合物δ-十二内酯：1）将十二烷酸转化为5-羟基十二烷酸（区域选择性为24％），在低pH内酰胺酶下可转化为δ-十二内酯，以及2）转化将1-十二烷醇转化为1,5-十二烷二醇（55％的区域选择性），可以通过马肝醇脱氢酶将其转化为δ-十二烷内酯。
• Simple Preparation of<i>Rhodococcus erythropolis</i>DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones
  作者：Enriqueta Martinez-Rojas、Teresa Olejniczak、Konrad Neumann、Leif-Alexander Garbe、Filip Boratyñski

  DOI：10.1002/chir.22623

  日期：2016.9

  In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane‐1,4‐diol (2a) and decane‐1,5‐diol (3a) into the corresponding γ‐ (2b) and δ‐decalactones (3b) with yield of 80% and enantiomeric excess (ee) = 75% and ee = 90%, respectively. Among oxidation of meso diols, (−)‐(1S,5R)‐cis‐3‐oxabicyclo[4

  在当前的研究中，我们提出了一个绿色的工具箱来生产生态化合物，如内酯部分。红球菌DSM 44534细胞已用于将癸烷-1,4-二醇（2a）和癸烷-1,5-二醇（3a）氧化成相应的γ-（2b）和δ-癸内酯（3b） 80％和对映体过量（ee）= 75％，ee = 90％。在内消旋二醇的氧化中，（-）-（1S，5R）-顺式-3-氧杂双环[4.3.0] non-7-en-2-1（5a）的产率为56％，ee = 76％，以及（ - ） - （2R，3S） -顺式-内切形成了100％收率且ee = 90％的-3-oxabicyclocyclo [2.2.1] dec-7-en-2-one（6a）。值得一提的是R.红球菌DSM 44534在含有乙醇作为能源和碳的唯一来源矿物培养基中生长手性28：623-627，2016。©2016 Wiley Periodicals，Inc.
• IBX/n-Bu4NBr/CH2Cl2–H2O: a new mild system for selective oxidation of secondary alcohols
  作者：Chutima Kuhakarn、Krisada Kittigowittana、Manat Pohmakotr、Vichai Reutrakul

  DOI：10.1016/j.tet.2005.07.051

  日期：2005.9

  A new alternative system for the chemoselective oxidation of secondary hydroxyl group to ketone with IBX/n-Bu4NBr in CH2Cl2–H2O has been developed. Under the reaction conditions, the secondary hydroxyl group was highly chemoselectively oxidized to the corresponding ketone, in moderate to good yields at rt, in the presence of primary hydroxyl group within the same molecule.

  开发了一种新的替代系统，用于在CH 2 Cl 2 -H 2 O中用IBX / n -Bu 4 NBr将仲羟基化学选择性氧化为酮。在反应条件下，在同一分子内存在伯羟基的情况下，仲羟基在室温下以中等至良好的收率被高度化学选择性氧化为相应的酮。
• The preparation of trialkylvinylborates and their reactions with oxiranes and with iodine. A facile synthesis of 1,4-alkanediols and 1-alkenes
  作者：K. Utimoto、K. Uchida、M. Yamaya、H. Nozaki

  DOI：10.1016/0040-4020(77)80381-5

  日期：1977.1

  Reaction of trialkylboranes with vinyllithium gives non-isolable lithium trialkylvinylborates which react with oxirane and methyloxirane affording 1,4- and 2,5-alkanediols, respectively. Treatment of trialkylboranes with vinylmagnesium bromide produces bromomagnesium trialkylvinylborates which analogously afford alkanediols. Successive treatment of the borates with aqueous alkali and iodine provides

  三烷基硼烷与乙烯基锂的反应得到不可分离的三烷基乙烯基硼酸锂，其与环氧乙烷和甲基环氧乙烷反应，分别得到1，4-和2，5-链烷二醇。用乙烯基溴化镁处理三烷基硼烷可得到三烷基乙烯基硼酸溴镁，类似地得到链烷二醇。用碱金属和碘水溶液连续处理硼酸盐可得到1-烯烃。