(2R,3S)-3,7-dimethyl-6-octene-1,2-diol | 156633-81-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,3S)-3,7-dimethyl-6-octene-1,2-diol
• 英文别名: (2R,3S)-3,7-dimethyloct-6-ene-1,2-diol
• CAS: 156633-81-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: YQXHFURSJJKJQK-UWVGGRQHSA-N

物化性质

• 沸点：
  285.2±28.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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,3S)-3,7-dimethyl-6-octene-1,2-diol 在 sodium periodate 、 sodium tetrahydroborate 作用下， 以 水 、 丙酮 、 甲醇 为溶剂， 反应 5.0h， 以81%的产率得到(2S)-2,6-dimethyl-5-hepten-1-ol
  参考文献：
  名称：

  两性霉素B的正式合成

  摘要：

  本文报道了两性霉素B（1）的有效，会聚和高度立体选择性的形式合成。在两性霉素B中，C10–C21（4）和C1–C9（5）片段分别来自香叶醇6和1,4-丁二醇7的单-PMB醚，分别以19和9的步骤衍生。合成中涉及的关键步骤是Sharpless不对称环氧化，Evans醛醇，Julia烯化，oxa-Michael，Keck烯丙基化，Mannich反应，Evans不对称烷基化和Yamaguchi酯化。

  DOI：

  10.1016/j.tet.2012.11.075
• 作为产物：
  描述：

  2,3-环氧-3,7-二甲基辛-6-烯醇 在 三氟化硼乙醚 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3S)-3,7-dimethyl-6-octene-1,2-diol
  参考文献：
  名称：

  Total Synthesis of (−)-5,6-Dihydrocineromycin B

  摘要：

  An asymmetric total synthesis of (-)-5,6-dihydrocineromycin B has been accomplished in 13 steps from (-)-linalool O-triethylsilyl ether or 12 steps from geraniol. The present synthesis features (i) an intermolecular Wittig reaction involving an aldehyde possessing a ketophosphonate functionality and (ii) an intramolecular Horner-Wadsworth-Emmons olefination.

  DOI：

  10.1021/jo802503x

文献信息

• Scope and Mechanism of the Pt-Catalyzed Enantioselective Diboration of Monosubstituted Alkenes
  作者：John R. Coombs、Fredrik Haeffner、Laura T. Kliman、James P. Morken

  DOI：10.1021/ja4041016

  日期：2013.7.31

  The Pt-catalyzed enantioselective diboration of terminal alkenes can be accomplished in an enantioselective fashion in the presence of chiral phosphonite ligands. Optimal procedures and the substrate scope of this transformation are fully investigated. Reaction progress kinetic analysis and kinetic isotope effects suggest that the stereodefining step in the catalytic cycle is olefin migratory insertion

  Pt 催化的末端烯烃的对映选择性二硼化可以在手性亚膦酸酯配体存在下以对映选择性方式完成。对这种转化的最佳程序和底物范围进行了充分研究。反应进程动力学分析和动力学同位素效应表明催化循环中的立体定义步骤是烯烃迁移插入 Pt-B 键。密度泛函理论分析与其他实验数据相结合，表明插入反应将铂定位在基板的内部碳上。该反应的立体化学模型得到了改进，该模型既符合这些特征又符合 Pt-配体复合物的晶体结构。
• Zeolite (H-ZSM 5) catalysed regio and stereoselective reduction of 2,3-epoxy alcohols to 1,2-diols and vinylic epoxides to homoallylic alcohols with sodium cyanoborohydride
  作者：Anuradha Gupta、Yashwant D. Vankar

  DOI：10.1016/s0040-4039(98)02610-0

  日期：1999.2

  positions) undergo reduction with zeolite H-ZSM 5/NaCNBH3 combination of reagent system in refluxing dichloroethane to give 1,2-diols and homoallylic alcohols in moderate to good yields. Under these conditions acid sensitive groups such as an acetal and a THP ether are not affected which indicates the mildness of the reaction conditions.

  在回流二氯乙烷中，用沸石H-ZSM 5 / NaCNBH 3组合试剂体系，将各种2,3-环氧醇和乙烯基环氧化合物（在末端位置具有环氧部分）还原，得到1,2-二醇和均丙醇中等至良好的产量。在这些条件下，不影响酸敏感性基团如缩醛和THP醚，这表明反应条件温和。
• Chiral Synthesis of the C_3-13 Segment of Epothilone A
  作者：Zhi-Yu Liu、Chen-Zhi Yu、Jia-De Yang

  DOI：10.1055/s-1997-1076

  日期：——

  Synthesis of the title compound using inexpensive geraniol as starting material in 13 steps and in 10.6% overall yield is described.

  以廉价的香叶醇为起始原料，通过 13 个步骤合成了标题化合物，总收率为 10.6%。
• Total Synthesis of (−)-Stellettamide B and Determination of Its Absolute Stereochemistry
  作者：Naoki Yamazaki、Wataru Dokoshi、Chihiro Kibayashi

  DOI：10.1021/ol0003228

  日期：2001.1.1

  [figure: see text] The first total synthesis of (-)-stellettamide B has been achieved by a sequence based on amide coupling of the chiral 1-(aminomethyl)-indolizidine fragment, prepared by TiCl4-mediated asymmetric allylation of the tricyclic N-acyl-N,O-acetal, with the chiral trienoic acid fragment. This synthesis led to revision of the published relative stereochemistry of the natural product and established

  [图：见正文]（-）-stellettamide B的第一个全合成是通过基于手性1-（氨基甲基）-吲哚并咪唑片段的酰胺偶联的序列实现的，该序列是由TiCl4介导的三环N的不对称烯丙基化制备的-酰基-N，O-乙缩醛，带有手性三烯酸片段。该合成导致对天然产物的公开相对立体化学的修订，并将其绝对立体化学确定为1S，4S，8aR，6” R。
• Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands
  作者：Christoph Naumann、Brian O. Patrick、John Sherman

  DOI：10.1002/1521-3765(20020816)8:16<3717::aid-chem3717>3.0.co;2-g

  日期：2002.8.16

  A [6]cavitand has been selectively derivatized on both the lower and upper rims. On the lower rim, two out of six potential sites were oxidized to produce a 1,4 substituted [6]cavitand bisketone, which was converted to a corresponding diol as well as a bisacetate [6]cavitand. The crystal structures of the bisketone and the diol were solved. On the upper rim, all six ArCH3 groups were selectively brominated to ArCH2Br groups to produce the hexabromomethyl [6]cavitand, which was converted to the corresponding hexabenzylthiol and hexabenzylthioacetate [6]cavitands. The conformational properties of all compounds are discussed.