(2R)-(-)-2,6-dimethyl-6-heptene-1,2-diol | 72129-06-7

• 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)-(-)-2,6-dimethyl-6-heptene-1,2-diol
• 英文别名: (R)-2,6-dimethylhept-6-ene-1,2-diol；2,6-dimethylhept-6-ene-1,2-diol；(R)-2,6-dimethyl-hept-6-ene-1,2-diol；(R)-2,6-dimethyl-6-heptene-1,2-diol；(2R)-2,6-dimethylhept-6-ene-1,2-diol
• CAS: 72129-06-7
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: CHBLMBLILJEDDS-SECBINFHSA-N

物化性质

• 沸点：
  265.6±28.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (2R)-(-)-2,6-dimethyl-6-heptene-1,2-diol 在 咪唑 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 草酰氯 、 三氟甲磺酸二丁硼 、 四丁基氟化铵 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 56.25h， 生成 (2R,3R,4R,8Z)-3-hydroxy-4-(methoxymethoxy)-2,4,8-trimethyldec-8-enolide
  参考文献：
  名称：

  The synthesis of 3-hydroxy-2,4,8-trimethyldec-8-enolides and an approach to 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide

  摘要：

  报道了对3、(E)-8、(Z)-8、20a和20b进行对映选择性合成，其中关键步骤是RCM。根据光谱差异，已将天然产物的结构修订为γ-丁内酯。

  DOI：

  10.1039/c4ob01792g
• 作为产物：
  描述：

  4-甲基-4-戊烯酸乙酯 在 lithium aluminium tetrahydride 、 magnesium 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 34.5h， 生成 (2R)-(-)-2,6-dimethyl-6-heptene-1,2-diol
  参考文献：
  名称：

  Chiral linker. Part 4: Diastereoselective addition of RZnX to α-keto esters using m-hydrobenzoin derived chiral auxiliaries in solution and on solid support and their application in the stereoselective synthesis of frontalin

  摘要：

  Two recently reported, m-hydrobenzoin derived open chain chiral auxiliaries, which were developed for application in either solution or immobilized on a solid support, were tested in the diastereoselective addition of RZnX to their corresponding phenylglyoxylates and pyruvates, respectively, resulting in diastereoisomeric excesses of up to > 98% de. The optimized procedure was applied in the stereoselective synthesis of frontalin, the aggregation pheromone of pine bark beetles of the Dendroctonus family, by the use of both the solution phase and the polymer supported chiral auxiliary. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.016

文献信息

• Asymmetric synthesis based on chiral diamines having pyrrolidine ring
  作者：Teruaki Mukaiyama

  DOI：10.1016/s0040-4020(01)93286-7

  日期：——

  Various highly stereoselective asymmetric reactions based on chiral diamines having pyrrolidine ring are described. Some of these reactions have been successfully applied to the syntheses of natural products.

  描述了基于具有吡咯烷环的手性二胺的各种高度立体选择性的不对称反应。这些反应中的一些已经成功地应用于天然产物的合成。
• ASYMMETRIC SYNTHESIS OF TWO ENANTIOMERS OF FRONTALIN
  作者：Yoji Sakito、Teruaki Mukaiyama

  DOI：10.1246/cl.1979.1027

  日期：1979.8.5

  (S)-Frontalin and its antipode were separately synthesized in good yields from (S)- and (R)-2-hydroxy-2,6-dimethyl-6-heptenal, which were prepared in high optical yields by an asymmetric synthesis using (S)- 2-(anilinomethyl)pyrrolidine as a chiral auxiliary.

  (S)-Frontalin 及其对映体分别由 (S)- 和 (R)-2-羟基-2,6-二甲基-6-庚烯醛以高产率分别合成，它们是通过不对称合成以高产率制备的(S)-2-(苯胺基甲基)吡咯烷作为手性助剂。
• Synthesis of (-)- and (+)-frontalin
  作者：James K. Whitesell、Charles M. Buchanan

  DOI：10.1021/jo00376a081

  日期：1986.12
• Enantiomerically pure acetals in organic synthesis. 2. Diastereoselective alkylation of enantiomeric lithio alkyl lactyl tetrahydropyranosides and related enolates
  作者：Eugene A. Mash、James A. Fryling

  DOI：10.1021/jo00003a035

  日期：1991.2

  A concise approach for the rapid synthesis of enantiomerically pure alpha-alkylated derivatives of lactate esters and of other enantiomerically pure alpha-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other alpha-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.
• MASH, EUGENE A.;FRYLING, JAMES A., J. ORG. CHEM., 56,(1991) N, C. 1094-1098
  作者：MASH, EUGENE A.、FRYLING, JAMES A.

  DOI：——

  日期：——