methyl (2R,4R,6R,8R)-2,4,6,8-tetramethyldecanoate | 2490-56-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (2R,4R,6R,8R)-2,4,6,8-tetramethyldecanoate
• CAS: 2490-56-4
• 化学式: C₁₅H₃₀O₂
• 分子量: 242.402
• InChiKey: IGBSZPRCTMBPTC-AAVRWANBSA-N

物化性质

• 沸点：
  255.4±8.0 °C(Predicted)
• 密度：
  0.862±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (2R,4R,6R,8R)-2,4,6,8-tetramethyldecanoate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 36.0h， 生成 (2R,4R,6R,8R)-2,4,6,8-Tetramethyldecansaeure-octadecylester
  参考文献：
  名称：

  Morr, Michael; Wray, Victor; Fortkamp, Jens, Liebigs Annalen der Chemie, 1992, # 5, p. 433 - 440

  摘要：

  DOI：

文献信息

• New chiral side chains for ferro- and antiferro-electric liquid crystals derived from the preen-gland wax of the domestic goose
  作者：Gerd Heppke、Detlef Lötzsch、Michael Morr、Ludger Ernst

  DOI：10.1039/a704503d

  日期：——

  (2R,4R,6R,8R)-2,4,6,8-Tetramethyldecanoic acid and (2R,4R,6R,8R)-2,4,6,8-tetramethyldecanol, as well as the (2R,4R,6R,8R) and the (2S,4R,6R,8R) diastereomers of 4,6,8-trimethyldecan-2-ol, have been obtained from the preen-gland wax of the domestic goose. Starting from these alkanols and alkanoic acid, novel ferro- and antiferro-electric liquid crystals bearing four methyl branchings in the chiral side chain have been synthesized and their mesomorphic and electro-optical properties have been investigated. The results obtained are compared with the properties of the respective chiral (S)-2-methyldecanoic acid, (S)-decan-2-ol and (S)-2-methyldecanol derivatives. The compounds with four methyl branchings in the chiral side chain are found to exhibit lower melting points, broader SmC* phase ranges, higher values of spontaneous polarization and larger tilt angles in comparison to the respective compound with only one methyl branching.

  从家鹅前腺蜡中获得了 (2R,4R,6R,8R)-2,4,6,8-四甲基癸酸和 (2R,4R,6R,8R)-2,4,6,8-四甲基癸醇，以及 4,6,8-三甲基癸-2-醇的 (2R,4R,6R,8R) 和 (2S,4R,6R,8R) 非对映异构体。以这些烷醇和烷酸为起点，合成了手性侧链中含有四个甲基分支的新型铁电和反铁电液晶，并研究了它们的介形和电光特性。研究结果与手性 (S)-2-甲基癸酸、(S)-2-癸醇和 (S)-2-甲基癸醇衍生物的特性进行了比较。与只有一个甲基支链的化合物相比，手性侧链上有四个甲基支链的化合物表现出更低的熔点、更宽的 SmC* 相范围、更高的自发极化值和更大的倾斜角。
• Chemoenzymatic Synthesis of the C3-C11-Fragment of Borrelidin
  作者：Matthias Theurer、Yana El Baz、Katja Koschorreck、Vlada B. Urlacher、Guntram Rauhut、Angelika Baro、Sabine Laschat

  DOI：10.1002/ejoc.201100412

  日期：2011.8

  The ex-chiral pool synthesis of the Theodorakis C3–C11 fragment of borrelidin (1) by a chemoenzymatic approach in nine steps and 12 % overall yield starting from enantiopure methyl-branched preen gland wax esters is described. In the initial reaction, the wax ester was (ω-1)-hydroxylated regioselectively by using a mutant of the cytochrome P450 monooxygenase CYP102A1 as biocatalyst. The fourthstereocenter

  描述了通过化学酶法在九个步骤中合成疏螺旋体 (1) 的 Theodorakis C3–C11 片段的手性池合成，从对映体纯甲基支化蓍腺蜡酯开始，总产率为 12%。在初始反应中，通过使用细胞色素 P450 单加氧酶 CYP102A1 的突变体作为生物催化剂，蜡酯被 (ω-1) 区域选择性羟基化。C3-C11 片段中的第四个立体中心是通过手性辅助介导的烷基化产生的。为了解释全顺式聚丙酸酯替代差向异构化的实验结果，在 B3LYP/cc-pVDZ 水平上进行了量子化学计算。
• Chiral Methyl-Branched Surfactants and Phospholipids: Synthesis and Properties
  作者：Michael Morr、Jens Fortkamp、Stefan Rühe

  DOI：10.1002/anie.199724601

  日期：1997.12.1
• Highly Branched Alkanoic Acids from the Preen-Gland Wax of the Domestic Goose as Building Blocks for Chiral Triphenylenes
  作者：Andreas Schultz、Sabine Laschat、Michael Morr、Siegmar Diele、Michael Dreyer、Gerhard Bringmann

  DOI：10.1002/1522-2675(200211)85:11<3909::aid-hlca3909>3.0.co;2-r

  日期：2002.11

  The synthesis of chiral triphenylenes 7a,b bearing side chains derived from enantiomerically pure trimethyloctanoate la and tetramethyldecanoate 1b from the preen-gland wax of domestic goose was achieved in 3 or 4 steps. Compounds 7a,b were nonmesogenic; however, mixtures of 7a,b with hexakis(octyloxy)triphenylene or hexakis(decyloxy)triphenylene displayed columnar mesophases or soft crystal G phases, as was shown by differential-scanning calorimetry and optical-polarizing microscopy. Circular-dichroism measurements revealed weak associations of 7a,b in solution.
• Morr, Michael; Wray, Victor; Fortkamp, Jens, Liebigs Annalen der Chemie, 1992, # 5, p. 433 - 440
  作者：Morr, Michael、Wray, Victor、Fortkamp, Jens、Schmid, Rolf D.

  DOI：——

  日期：——