(+/-)-(2R^*,4R^*,6S^*)-methyl 6-hydroxy-2,4-dimethylheptanoate

• 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: (+/-)-(2R^*,4R^*,6S^*)-methyl 6-hydroxy-2,4-dimethylheptanoate
• 英文别名: methyl (2R^*,4S^*,6S^*)-6-hydroxy-2,4-dimethyl-heptanoate；methyl (2RS,4SR,6SR)-6-hydroxy-2,4-dimethylheptanoate；methyl 6-hydroxy-2,4-dimethylheptanoate；methyl (2R,4S,6S)-6-hydroxy-2,4-dimethylheptanoate
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: DKLYCLXAHDLYOB-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-(2R^*,4R^*,6S^*)-methyl 6-hydroxy-2,4-dimethylheptanoate 在 4-二甲氨基吡啶 、 lithium hydroxide 、 氢氟酸 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 73.58h， 生成 (2R^*,4s^*,6S^*)-2,6-dibenzoyloxy-4-methyl-heptane
  参考文献：
  名称：

  Conformation preferences in 2,4,6-trisubstituted heptanes

  摘要：

  The preference of (2R*,4r*,6S*)-2,4,6-trichloroheptane (6) for populating the fully extended conformation mirrors the local conformational preferences of the 2,4-dichloropentane subunits. Likewise, the preference of (2R*,4r*,6S*)-2,6-dichloro-4-methyl-heptane (9) to populate the extended conformation mirrors that of the 2-chloro-4-methyl-heptane subunits. There is therefore no cooperative effect (neither positive nor negative) between the 2,4-disubstituted pentane subunits in determining the conformer preferences of the 2,4,6-trisubstituted heptanes studied. (C) Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00349-x
• 作为产物：
  描述：

  N-<(2R,4S,6S)-2,4-dimethyl-6-(3,5-dinitrobenzoyloxy)heptanoyl>-O-(3,5-dinitrobenzoyl)-(S)-prolinol 在 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 2.17h， 生成 (+/-)-(2R^*,4R^*,6S^*)-methyl 6-hydroxy-2,4-dimethylheptanoate
  参考文献：
  名称：

  Synthesis of both the enantiomers of lardolure, the aggregation pheromone of the acarid mite,

  摘要：

  DOI：

  10.1016/s0040-4020(01)88157-6

文献信息

• A cross metathesis strategy for the synthesis of highly functionalized conjugated cyanodienes: synthesis of the C3–C17 framework of (−)-borrelidin
  作者：C. Vamsee Krishna、Vasudev R. Bhonde、A. Devendar、Santanu Maitra、K. Mukkanti、Javed Iqbal

  DOI：10.1016/j.tetlet.2008.01.055

  日期：2008.3

  A cross metathesis strategy for the synthesis of highly functionalized conjugated cyanodienes was developed and was successfully applied in the synthesis of the C3–C17 framework of (−)-borrelidin.

  开发了一种交叉复分解策略，用于合成高度官能化的共轭氰基二烯，并成功地用于合成（-）-硼瑞林的C3–C17构架。
• Synthesis of (2R,4R)-Supellapyrone, the Sex Pheromone of the Brownbanded Cockroach,Supella longipalpa, and Its Three Stereoisomers
  作者：Ken Fujita、Kenji Mori

  DOI：10.1002/1099-0690(200102)2001:3<493::aid-ejoc493>3.0.co;2-b

  日期：2001.2

  Supellapyrone [(2R,4R)-5-(2,4-dimethyl)-3-methyl-2H-pyran-2-one (1)], the female sex pheromone of the brownbanded cockroach (Supella longipalpa), and its three stereoisomers were synthesized by employing Iipase-catalyzed desymmetrization or enantiomer separation of syn- or anti-2,4-dimethylpentane- 1,5-diol (9) as the key step.
• Stereochemistry of lardolure
  作者：Kenji Mori、Shigefumi Kuwahara

  DOI：10.1016/s0040-4020(01)88158-8

  日期：1986.1
• Conformation Induction Between Neighboring Dimethylpentane Segments
  作者：Reinhard W. Hoffmann、Richard Göttlich、Ulrich Schopfer

  DOI：10.1002/1099-0690(200105)2001:10<1865::aid-ejoc1865>3.0.co;2-e

  日期：2001.5

  A 2,4-dimethylpentane unit can be rendered monoconformational by the presence of a conformation-inducing group (an inductor group) at C-1 (cf. 6). The resulting entity may serve as an inductor group to control in turn the conformation of a neighboring dimethylpentane segment (cf. 7). This holds if the inducing dimethylpentane segment is isotactic (cf. 15, 25), but not when it is syndiotactic (cf. 28).
• 4,6,8,10,16-Penta- and 4,6,8,10,16,18-Hexamethyldocosanes from the Cane Beetle <i>Antitrogus </i><i>p</i><i>arvulus</i> - Cuticular Hydrocarbons with Unprecedented Structure and Stereochemistry
  作者：Mary T. Fletcher、Sharon Chow、Lynette K. Lambert、Oliver P. Gallagher、Bronwen W. Cribb、Peter G. Allsopp、Christopher J. Moore、William Kitching

  DOI：10.1021/ol0361453

  日期：2003.12.1

  [GRAPHICS]The major cuticular hydrocarbons from the cane beetle species Antitrogus parvulus were deduced to be 4,6,8,10,16,18-hexa- and 4,6,8,10,16-pentamethyldocosanes 2 and 3, respectively. Isomers of 2,4,6,8-tetramethylundecanal 27, 36, and 37, derived from 2,4,6-trimethylphenol, were coupled with the phosphoranes 28 and 29 to furnish alkenes and, by reduction, diastereomers of 2 and 3. Chromatographic and spectroscopic comparisons confirmed 2 as either 6a or 6b and 3 as either 34a or 34b.