(S)-2-(hex-1-en-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1267551-51-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: (S)-2-(hex-1-en-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-[(3S)-hex-1-en-3-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1267551-51-8
• 化学式: C₁₂H₂₃BO₂
• 分子量: 210.124
• InChiKey: HOCVDXQMUXMTEZ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(hex-1-en-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 双氧水 、 sodium hydroxide 作用下， 以 乙醚 、 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 (3S)-hex-1-en-3-ol
  参考文献：
  名称：

  迭代不对称烯丙基取代：通过催化剂控制的顺式和反式1,2-二醇

  摘要：

  铜催化的不对称烯丙基硼化（AAB）使人们可以合成顺式和反式1,2-二醇。该方法便于迭代策略多元醇（参见方案），如完全分化的制备大号-ribo-四醇和保护d -arabino-四醇。P =保护基

  DOI：

  10.1002/anie.201107874
• 作为产物：
  描述：

  顺-2-己烯-1-醇 在 甲醇 、 (2S,3S)-(6-(4-tert-butyl-2,6-dimethylphenyl)-2,3-diphenyl-2,3,5,6-tetrahydroimidazo[1,2-c]quinazolin-5-yl)copper(I) chloride 、 sodium hydride 、 sodium t-butanolate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 (S)-2-(hex-1-en-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Stereoconvergent Synthesis of Chiral Allylboronates from an E/Z Mixture of Allylic Aryl Ethers Using a 6-NHC−Cu(I) Catalyst

  摘要：

  We present a 6-NHC-Cu(I) complex that provides alpha-substituted allylboronates using allylic aryl ether substrates. The method was discovered by comparison of the chemoselectivities exhibited by complexes 1a, 1b, 2, and 3. We observed that 1a preferentially reacts with electron-rich alkenes over electron-deficient alkenes. Development of an asymmetric method revealed that 1b reacts with both the E and Z isomers to provide the same absolute configuration without showing E-Z isomerization. This stereoconvergent reaction occurs with high yields (av 86%), high S(N)2` selectivity (> 99:1), and high ee (av 94%) and exhibits wide functional-group tolerance using pure E or Z isomer or E/Z alkene mixtures. The stereoconvergent feature enables the use of many different olefination strategies for substrate production, including cross-metathesis. Chiral allylboronates could be purified by silica gel chromatography and stored in the freezer without decomposition.

  DOI：

  10.1021/ja1112518

文献信息

• Stereoconvergent Synthesis of Chiral Allylboronates from an <i>E</i>/<i>Z</i> Mixture of Allylic Aryl Ethers Using a 6-NHC−Cu(I) Catalyst
  作者：Jin Kyoon Park、Hershel H. Lackey、Brian A. Ondrusek、D. Tyler McQuade

  DOI：10.1021/ja1112518

  日期：2011.3.2

  We present a 6-NHC-Cu(I) complex that provides alpha-substituted allylboronates using allylic aryl ether substrates. The method was discovered by comparison of the chemoselectivities exhibited by complexes 1a, 1b, 2, and 3. We observed that 1a preferentially reacts with electron-rich alkenes over electron-deficient alkenes. Development of an asymmetric method revealed that 1b reacts with both the E and Z isomers to provide the same absolute configuration without showing E-Z isomerization. This stereoconvergent reaction occurs with high yields (av 86%), high S(N)2` selectivity (> 99:1), and high ee (av 94%) and exhibits wide functional-group tolerance using pure E or Z isomer or E/Z alkene mixtures. The stereoconvergent feature enables the use of many different olefination strategies for substrate production, including cross-metathesis. Chiral allylboronates could be purified by silica gel chromatography and stored in the freezer without decomposition.
• Iterative Asymmetric Allylic Substitutions: syn- and anti-1,2-Diols through Catalyst Control
  作者：Jin Kyoon Park、D. Tyler McQuade

  DOI：10.1002/anie.201107874

  日期：2012.3.12

  A copper‐catalyzed asymmetric allylic boronation (AAB) gives access to syn‐ and anti‐1,2‐diols. The method facilitates an iterative strategy for the preparation of polyols (see scheme), such as the fully differentiated L‐ribo‐tetrol and protected D‐arabino‐tetrol. P=protecting group

  铜催化的不对称烯丙基硼化（AAB）使人们可以合成顺式和反式1,2-二醇。该方法便于迭代策略多元醇（参见方案），如完全分化的制备大号-ribo-四醇和保护d -arabino-四醇。P =保护基