(1R,1'R,5'R,7'R)-1-(5'-methyl-6',8'-dioxabicyclo[3.2.1]octan-7'-yl)ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,1'R,5'R,7'R)-1-(5'-methyl-6',8'-dioxabicyclo[3.2.1]octan-7'-yl)ethanol
• 英文别名: (-)-(1R,1’R,5’R,7’R)-1-hydroxy-exo-brevicomin；(+)-(1R)-1-hydroxy-exo-brevicomin；(aR,1R,5R,7R)-a,5-Dimethyl-6,8-dioxabicyclo[3.2.1]octane-7-methanol；1-hydroxybrevicomin；(1R)-1-[(1R,5R,7R)-5-methyl-6,8-dioxabicyclo[3.2.1]octan-7-yl]ethanol
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: AMFJBCFUEJFUFK-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-oxohexanal 在 AD-mix-β 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 6.0h， 生成 (1R,1'R,5'R,7'R)-1-(5'-methyl-6',8'-dioxabicyclo[3.2.1]octan-7'-yl)ethanol
  参考文献：
  名称：

  的不对称合成（1 - [R，1 ' - [R，5 ' - [R，7 ' - [R ）和（1级小号，1 ' - [R，5 ' - [R，7 ' - [R）-1-羟基-外型-brevicomin和正式合成（ +）- exo -brevicomin

  摘要：

  的不对称合成（1 - [R，1 ' - [R，5 ' - [R，7 ' - [R ）和（1级小号，1 ' - [R，5 ' - [R，7 ' - [R）-1-羟基-外型-brevicomins 1和2，挥发性物质的雄性山松甲虫和（+）- exo -brevicomin 3的正式合成，这是几个树皮甲虫的吸引信息素系统的组成部分。关键步骤是降低市场上可买到的α-甲基吡啶的桦木，选择性Wittig烯烃化反应和Sharpless不对称二羟基化反应。

  DOI：

  10.1016/j.tetlet.2003.12.157

文献信息

• Stereoselective Synthesis of (−)-(1<i>R</i>,1′<i>R</i>,5′<i>R</i>,7′<i>R</i>)-1-Hydroxy-<i>exo</i>-brevicomin and (+)-<i>exo</i>-Brevicomin from 3,4,6-Tri-<i>O</i>-acetyl-<scp>D</scp>-glucal
  作者：Gowravaram Sabitha、Arekuti Maheswara Reddy、Singam Siva Sankara Reddy、Jhillu Singh Yadav

  DOI：10.1002/hlca.201200611

  日期：2013.8

  Stereoselective syntheses of (−)‐(1R,1′R,5′R,7′R)‐1‐hydroxy‐exo‐brevicomin (1) and (+)‐exo‐brevicomin (2) were accomplished from 3,4,6‐tri‐O‐acetyl‐D‐glucal (5; Schemes 2 and 3). Chemoselective reduction, Grignard reaction, BartonMcCombie deoxygenation, and ketalization were used as key steps.

  的立体选择性合成（ - ） - （1 - [R，1' - [R，5' - [R，7' - [R）-1-羟基-外型-brevicomin（1）和（+） -外-brevicomin（2）从3完成的， 4,6-三-O-乙酰基-D-葡糖（5 ;方案2和3）。化学选择性还原，格氏反应，巴顿 McCombie脱氧，和缩酮化被用作关键步骤。
• Pheromone Synthesis, CLXXXII. Synthesis of (1R,1′R,5′R,7′R)- and (1S,1′R,5′R,7′R)- 1-hydroxy-exo-Brevicomin, the Components of the Male-Produced Volatiles of the Mountain Pine Beetle,dendroctonus ponderosae
  作者：Yūsuke Yokoyama、Kenji Mori

  DOI：10.1002/jlac.199719970509

  日期：1997.5

  Both (1R)- and (1S)-hydroxy derivatives of (+)-exo-brevicomin (1R,1′R,5′R,7′R)-1-(5′-methyl-6′,8′-dioxabicyclo[3.2.1]-octyl)ethanol (1) and its (1S)-isomer (2)} were synthesized by employing Sharpless asymmetric dihydroxylation as the key reaction.

  两者（1 - [R ）-和（1小号）的羟基衍生物（+） -外- brevicomin （1 - [R，1' - [R，5' - [R，7' - [R）-1-（5'-甲基-6'以Sharpless不对称二羟基化为关键反应，合成了1,8'-二氧杂双环[3.2.1]-辛基）乙醇（1）及其（1S）-异构体（2）}。
• Highly α-Selective Hydrolysis of α,β-Epoxyalcohols using Tetrabutylammonium Fluoride
  作者：Purba Mukerjee、Mohammed Abid、Frank C. Schroeder

  DOI：10.1021/ol1015306

  日期：2010.9.17

  We report a simple method for the highly regio- and stereoselective hydrolysis of alpha,beta-epoxyalcohols. Treatment of enantiopure epoxyalcohols derived from Sharpless epoxidation with TBAF/H(2)O resulted in exclusive ring opening at the normally disfavored alpha-position, providing access to arabino- or lyxo-configured triols with full preservation of stereochemical purity. The method was applied in syntheses of 5-deoxy-L-arabinose (26) and a family of bicyclic acetals based on the insect pheromone hydroxybrevicomin (4).
• Asymmetric syntheses of (1R,1′R,5′R,7′R) and (1S,1′R,5′R,7′R)-1-hydroxy-exo-brevicomin and a formal synthesis of (+)-exo-brevicomin
  作者：D. Naveen Kumar、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2003.12.157

  日期：2004.3

  Asymmetric syntheses of (1R,1′R,5′R,7′R) and (1S,1′R,5′R,7′R)-1-hydroxy-exo-brevicomins 1 and 2, volatiles of the male mountain pine beetle, and a formal synthesis of (+)-exo-brevicomin 3, a component of the attracting pheromone system of several bark beetles have been achieved. The key steps are Birch reduction of commercially available α-picoline, selective Wittig olefination, and Sharpless asymmetric

  的不对称合成（1 - [R，1 ' - [R，5 ' - [R，7 ' - [R ）和（1级小号，1 ' - [R，5 ' - [R，7 ' - [R）-1-羟基-外型-brevicomins 1和2，挥发性物质的雄性山松甲虫和（+）- exo -brevicomin 3的正式合成，这是几个树皮甲虫的吸引信息素系统的组成部分。关键步骤是降低市场上可买到的α-甲基吡啶的桦木，选择性Wittig烯烃化反应和Sharpless不对称二羟基化反应。