(R)-2-methyloctane-1,2-diol | 170209-34-4

• 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: (R)-2-methyloctane-1,2-diol
• 英文别名: 1,2-Octanediol, 2-methyl-, (2R)-；(2R)-2-methyloctane-1,2-diol
• CAS: 170209-34-4
• 化学式: C₉H₂₀O₂
• 分子量: 160.257
• InChiKey: MJGRMZVPQKMBKC-SECBINFHSA-N

物化性质

• 沸点：
  243.1±8.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (R)-2-methyloctane-1,2-diol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 1-Methoxy-4-((R)-2-methoxy-2-methyl-octyloxymethyl)-benzene
  参考文献：
  名称：

  手性仲醇衍生物手性季α-氧化醛的立体有择构建

  摘要：

  由受保护的手性仲醇1制备的手性叔二氯甲基甲醇衍生物2在弱碱性条件(K 2 CO 3 /MeOH/rt)下经由中间α-氯环氧化物3立体定向地转化为手性季α-氧化醛衍生物4和11。证明生成四元中心的方式因底物而异：非苄基底物 2a 的构型反转和苄基底物 2b 的表观保留。

  DOI：

  10.1055/s-2004-815406
• 作为产物：
  描述：

  (E)-1-bromo-2-methyloct-1-ene 在 C₃₄H₃₈Cl₂F₆FeP₂Pd 、 臭氧 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 54.21h， 生成 (R)-2-methyloctane-1,2-diol
  参考文献：
  名称：

  Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides

  摘要：

  Under the influence of a chiral palladium catalyst, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate nonracemic allyl boronates with high levels of enantioselectivity. The so-formed allyl boronates may be oxidized with hydrogen peroxide to provide secondary allylic alcohols or with nitrosobenzene to furnish nonracemic tertiary allylic alcohols. Mechanistic experiments suggest the operation of a pathway involving outer-sphere stereoinvertive transmetalation.

  DOI：

  10.1021/ja510266x

文献信息

• Studies on the Asymmetric Dihydroxylation of Advanced Bryostatin C-Ring Segments
  作者：H. Martin Hoffmann、Martin C. Seidel、René Smits、Christian B. Stark、Jens Frackenpohl、Oliver Gaertzen

  DOI：10.1055/s-2004-822400

  日期：——

  The asymmetric dihydroxylation reaction of early stage and advanced Bryostatin C-ring precursors was evaluated. For homoallylic ethers and alcohols, several AD ligands were investigated including a novel class of quinidine-alkynes.

  早期和进阶 Bryostatin C 环前体的不对称二羟基化反应被评估。对于高同位醚和醇，研究了多种 AD 配体，包括一类新型的奎尼丁炔。
• Nonracemic Allylic Boronates through Enantiotopic-Group-Selective Cross-Coupling of Geminal Bis(boronates) and Vinyl Halides
  作者：Bowman Potter、Adam A. Szymaniak、Emma K. Edelstein、James P. Morken

  DOI：10.1021/ja510266x

  日期：2014.12.31

  Under the influence of a chiral palladium catalyst, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate nonracemic allyl boronates with high levels of enantioselectivity. The so-formed allyl boronates may be oxidized with hydrogen peroxide to provide secondary allylic alcohols or with nitrosobenzene to furnish nonracemic tertiary allylic alcohols. Mechanistic experiments suggest the operation of a pathway involving outer-sphere stereoinvertive transmetalation.
• Stereospecific Construction of Chiral Quaternary α-Oxygenated Aldehydes from Chiral Secondary Alcohol Derivatives
  作者：Yukio Masaki、Hideki Arasaki、Masashi Iwata、Daisuke Nishimura、Akichika Itoh

  DOI：10.1055/s-2004-815406

  日期：——

  Chiral tertiary dichloromethylcarbinol derivatives 2, prepared from protected chiral secondary alcohols 1, were converted stereospecifically into chiral quaternary α-oxygenated aldehyde derivatives 4 and 11 via intermediary α-chloroepoxides 3 under weakly basic conditions (K 2 CO 3 /ΜeOH/r.t.). The fashion generating the quaternary centers was proved to be quite different depending on the substrates:

  由受保护的手性仲醇1制备的手性叔二氯甲基甲醇衍生物2在弱碱性条件(K 2 CO 3 /MeOH/rt)下经由中间α-氯环氧化物3立体定向地转化为手性季α-氧化醛衍生物4和11。证明生成四元中心的方式因底物而异：非苄基底物 2a 的构型反转和苄基底物 2b 的表观保留。