(2S,3S)-3,7-Dimethyloct-6-ene-1,2-diol | 156633-82-8

• 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: (2S,3S)-3,7-Dimethyloct-6-ene-1,2-diol
• 英文别名: (2S,3S)-3,7-dimethyl-6-octene-1,2-diol
• CAS: 156633-82-8
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: YQXHFURSJJKJQK-VHSXEESVSA-N

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：

  (2S,3S)-3,7-Dimethyloct-6-ene-1,2-diol 在 sodium hydroxide 、 sodium tetrahydroborate 、 copper(I) bromide dimethylsulfide complex 、 苄基三乙基氯化铵 、 sodium hydride 、 magnesium 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 32.83h， 生成 (6S,7R)-2,6-dimethyl-7-phenylmethoxy-3-phenylselanylundecan-2-ol
  参考文献：
  名称：

  The 2-Hydroxycitronellols, Convenient Chirons for Natural Products Synthesis

  摘要：

  DOI：

  10.1021/jo00093a037
• 作为产物：
  描述：

  (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 在 三氟化硼乙醚 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 以67%的产率得到(2S,3S)-3,7-Dimethyloct-6-ene-1,2-diol
  参考文献：
  名称：

  The 2-Hydroxycitronellols, Convenient Chirons for Natural Products Synthesis

  摘要：

  DOI：

  10.1021/jo00093a037

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。
• Regioselective Biotransformation of (+)- and (−)-Citronellene by the Larvae of Common Cutworm (Spodoptera litura)
  作者：Mitsuo Miyazawa、Shinsuke Marumoto、Atsunori Masuda、Haruki Kano、Hiromune Takechi

  DOI：10.1021/jf9009069

  日期：2009.9.9

  Terpenoids, which have many biological activities and have occurred widely in nature, can be artificially synthesized. However, regioselective oxidation of terpenoids is difficult by chemical methods. In this study, (+)- and (-)-citronellene were biotransformed with Spodoptera litura to define the mechanism of metabolism of citronellene and gain a new natural terpenoid. (+)-Citronellene was converted to (2S,3S)-3,7-dimethyl-6-octene-1,2-diol and (2R,3S)-3,7-dimethyl-6octene-1,2-diol (89.7%), (3S,6S)-(-)-3,7-dimethyl-1-octene-6,7-diol (3.8%), (3S)-(6E)-(+)-3,7-dimethyl-1,6-octadien-8-ol (4.2%), and (3S)-(6E)-(+)-3,7-dimethyl-1,6-octadien-8-oic acid (2.3%). In contrast, (-)-citronellene was converted to (2R,3R)-3,7-dimethyl-6-octene-1,2-diol and (2S,3R)-3,7dimethyl-6-octene-1,2-diol (56.3%), (+)-iridan-7,8-diol (3.5%), and (3R)-(6E)-(-)-3,7-dimethyl-1,6-octadien-8-oic acid (40.2%). The main metabolic pathway of (+)- and (-)-citronellene by larvae of S. litura was oxidized at the terminal double bond and trans-allylic methyl position. Particularly on (+)citronellene, the regioselective reaction was shown. On the oxidation of C-6, C-7, and C-8 positions, four new compounds (3S,6S)-(-)-3,7-dimethyl-1-octene-6,7-diol, (3S)-(6E)-(+)-3,7-dimethyl-1,6-octadien-8-oic acid, (+)-iridan-7,8-diol, and (3R)-(6E)-(-)-3,7-dimethyl-1,6-octadien-8-oic acid were produced in regioselective oxidation. It noted that stereoselective oxidation occurred between the enantiomers. The C-6 position was oxidized on the (+)-(3S) form, whereas cyclized and the C-7 position were oxidized on the (-)-(3R) form.
• The 2-Hydroxycitronellols, Convenient Chirons for Natural Products Synthesis
  作者：Douglass F. Taber、Jonathan B. Houze

  DOI：10.1021/jo00093a037

  日期：1994.7