docosane-11,12-dione | 18229-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: docosane-11,12-dione
• CAS: 18229-34-0
• 化学式: C₂₂H₄₂O₂
• 分子量: 338.574
• InChiKey: PAYMZYPCKZSAPD-UHFFFAOYSA-N

物化性质

• 沸点：
  416.7±14.0 °C(Predicted)
• 密度：
  0.877±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  24
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-二氨基噻吩二氢溴酸盐 、 docosane-11,12-dione 以 乙醇 为溶剂， 反应 3.0h， 以97%的产率得到2,3-didecylthieno[3,4-b]pyrazine
  参考文献：
  名称：

  噻吩并[3,4-b]吡嗪：合成，结构和反应性。

  摘要：

  已经开发了用于有效制备2，3-二取代的噻吩并[3，4-b]吡嗪的通用合成途径。这些方法消除了前体3，4-二氨基噻吩的制备中的问题，并利用了通过适当的有机铜酸酯与草酰氯反应而制备的α-二酮。这种结合使得可以方便地高产率地制备噻吩并[3，4-b]吡嗪及其2，3-二取代的类似物（其中取代基＝甲基，己基，辛基，癸基，十二烷基和苯基）。还描述了这类化合物的结构和反应性，包括结构，电化学和pK（a）研究的结果。

  DOI：

  10.1021/jo0262255
• 作为产物：
  描述：

  1,4-二甲基哌嗪-2,3-二酮 以70%的产率得到
  参考文献：
  名称：

  Mueller-Westerhoff Ulrich T., Zhou Ming, J. Org. Chem, 59 (1994) N 17, S 4988-4992

  摘要：

  DOI：

文献信息

• Long-chain acyloins and vicinal diketones
  作者：D. E. Ames、G. Hall、B. T. Warren

  DOI：10.1039/j39680002617

  日期：——

  Several methods for the preparation of long-chain vicinal diketones are examined. The acyloin condensation, followed by oxidation, provides an excellent route to symmetrical compounds but is not satisfactory for unsymmetrical diketones. The latter are prepared (i) from dialkylacetylenes by semihydrogenation, hydroxylation, and oxidation with aqueous N-bromosuccinimide; and (ii) from an α-acetoxy-acid

  研究了制备长链邻二酮的几种方法。酰基转移酶缩合，然后进行氧化，提供了一种制备对称化合物的极佳途径，但对于不对称二酮而言并不令人满意。后者由（i）由二烷基乙炔经半氢化，羟基化和用N-溴代琥珀酰亚胺水溶液氧化而制得；（ii）由α-乙酰氧基酰氯和双四氢吡喃基或二苄基烷基丙二酸酯的钠衍生物衍生，然后除去保护基并脱羧得到α-乙酰氧基-酮，然后将其水解和氧化。
• Catalytic Action of Azolium Salts. VI. Preparation of Benzoins and Acyloins by Condensation of Aldehydes Catalyzed by Azolium Salts.
  作者：Akira MIYASHITA、Yumiko SUZUKI、Ken-ichi IWAMOTO、Takeo HIGASHINO

  DOI：10.1248/cpb.42.2633

  日期：——

  Benzoins 4 (2-hydroxyethanones substituted with aryl groups at the 1- and 2-positions) were prepared by self-condensation of aromatic aldehydes 3 using catalytic amounts of azolium salts 1 and 2 in excellent yields.1, 3-Dimethylbenzimidazolium iodide (2) was an effective catalyst for the preparation of acyloins 6 (2-hydroxyethanones substituted with alkyl groups at the 1- and 2-positions) by self-condensation of aliphatic aldehydes 5. On the other hand, an attempt at the condensation of hexanal (5d) catalyzed by 1, 3-dimethylimidazolium iodide (1) failed to yield the acyloin 6d, and instead the aldol-type condensed product 8d was obtained.

  苯偶姻 4（在 1- 和 2-位置上带有芳基取代的 2-羟基乙酮）通过使用少量的唑盐 1 和 2 作为催化剂，由芳香醛 3 的自缩合反应高效制备得到。1,3-二甲基苯并咪唑碘盐（2）是制备乙偶姻 6（在 1- 和 2-位置上带有烷基取代的 2-羟基乙酮）的有效催化剂，通过脂肪醛 5 的自缩合反应实现。另一方面，使用 1,3-二甲基咪唑碘盐（1）催化己醛（5d）的缩合反应未能得到乙偶姻 6d，而是得到了醛醇型缩合产物 8d。
• A direct access to α-diones from oxalyl chloride
  作者：Francesco Babudri、Vito Fiandanese、Giuseppe Marchese、Angela Punzi

  DOI：10.1016/0040-4039(95)01471-s

  日期：1995.10

  Cross-coupling reactions of oxalyl chloride with organocopper reagents, derived from Grignard reagents, cuprous bromide, and lithium bromide, provide a simple and straightforward method for the synthesis of symmetrical α-diones in very good yields.

  草酰氯与衍生自格氏试剂，溴化亚铜和溴化锂的有机铜试剂的交叉偶联反应为合成对称α-二酮提供了一种简单直接的方法，产率很高。
• Synthesis of Symmetrically and Unsymmetrically Substituted .alpha.-Diones from Organometallic Reagents and 1,4-Dialkylpiperazine-2,3-diones
  作者：Ulrich T. Mueller-Westerhoff、Ming Zhou

  DOI：10.1021/jo00096a049

  日期：1994.8

  The reaction of an equimolar mixture of N,N'-dialkylethylenediamines and diethyl oxalate in diethyl ether or 2-propanol leads to 1,4-dialkylpiperazine-2,3-diones. As cyclic and nearly planar tetraalkyl oxamides, these compounds are able to react with 2 equiv of organolithium or Grignard compounds to form, after hydrolysis, symmetrically substituted alpha-diones in excellent yields. The sequential addition of 1 equiv each of two different organolithium compounds affords unsymmetrically substitute alpha-diones when the more soluble longer chain dialkyl derivatives of piperazine-2,3-dione are employed. The dialkylethylenediamines can conveniently be recovered and recycled to the 1,4-dialkylpiperazine-2,3-diones in good yields.
• A simple synthesis of symmetrical α-diones from organometallic reagents and 1,4-dimethyl-piperazine-2,3-dione
  作者：Ulrich T. Mueller-Westerhoff、Ming Zhou

  DOI：10.1016/s0040-4039(00)61622-2

  日期：1993.1

  Short reflux of an equimolar mixture of N,N'-dimethyl ethylenediamine and diethyl oxalate in i-propanol or diethyl ether leads to 1,4-dimethyl-piperazine-2,3-dione, which is able to react with two equivalents of organolithium or Grignard compounds to form symmetrically substituted alpha-diones in excellent yields.