2-((2S,3S)-3-Pentyl-oxiranyl)-ethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 2-((2S,3S)-3-Pentyl-oxiranyl)-ethanol
• 英文别名: 2-[(2S,3S)-3-pentyloxiran-2-yl]ethanol
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: WPCFNWDALBRTFM-IUCAKERBSA-N

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：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((2S,3S)-3-Pentyl-oxiranyl)-ethanol 在 titanium(IV) isopropylate 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以80%的产率得到(3S,4R)-4-Iodo-nonane-1,3-diol
  参考文献：
  名称：

  Mild and stereocontrolled synthesis of iodo- and bromohydrins by halogen-tetrakis(isopropoxy)titanium opening of epoxy alcohols

  摘要：

  DOI：

  10.1021/jo00298a002
• 作为产物：
  描述：

  3-壬烯-1-醇,(3E)- 在 过氧化氢异丙苯 、 三异丙氧基氧化钒 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以89%的产率得到2-((2S,3S)-3-Pentyl-oxiranyl)-ethanol
  参考文献：
  名称：

  Vanadium-Catalyzed Asymmetric Epoxidation of Homoallylic Alcohols

  摘要：

  New chiral bishydroxamic acids were synthesized and tested as chiral ligands in the vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols to provide good yields and high enantioselectivities.

  DOI：

  10.1021/ja067495y

文献信息

• Boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols
  作者：Hongqing Yao、Jiawei Liu、Chuan Wang

  DOI：10.1039/c8ob02141d

  日期：——

  In this protocol we described a boronic acid-catalysed C-3 selective ring opening of 3,4-epoxy alcohols with thiophenols and thiols as nucleophiles. This diastereo- and enantiospecific reaction provides an efficient entry to prepare a variety of hydroxyl sulfides. Through the directing effect of the hydroxyl group, nucleophilic attack on the C-3 position of the epoxide moiety is favoured. It can be

  在该协议中，我们描述了硼酸催化的3,4-环氧醇的C-3选择性开环，其中硫酚和硫醇为亲核试剂。这种非对映和对映体特异性反应为制备各种羟基硫化物提供了有效的途径。通过羟基的指导作用，促进了对环氧化物部分的C-3位置的亲核攻击。可以在拟议的过渡态下进行合理化处理，其中硼酸催化剂将环氧化物和S-亲核体束缚在一起。
• Boronic Acid Catalyzed Regioselective Aminolysis of 3,4-Epoxy Alcohols
  作者：Jiawei Liu、Hongqing Yao、Chuan Wang

  DOI：10.1021/acscatal.8b02591

  日期：2018.10.5

  homoallylic alcohols has been accomplished, which was catalyzed by a commercially available boronic acid. Due to the directing effect of the hydroxyl moiety, the ring opening reaction of a variety of 3,4-epoxy alcohols bearing different substitution patterns with various aromatic amines as nucleophiles proceeded in a stereospecific reaction pathway at the C-3 position furnishing various amino alcohols as products

  环氧均烯丙基醇的C-3氨解反应已经完成，这是由市售的硼酸催化的。由于羟基部分的指导作用，当亲核试剂在C-3位的立体特异性反应途径中进行时，带有不同取代方式的各种3,4-环氧醇与各种芳香胺的开环反应会产生各种氨基醇以高度区域选择性的方式作为产品。
• Design of a New Bimetallic Catalyst for Asymmetric Epoxidation and Sulfoxidation
  作者：Sukalyan Bhadra、Matsujiro Akakura、Hisashi Yamamoto

  DOI：10.1021/jacs.5b11429

  日期：2015.12.23

  A new chiral tethered 8-quinolinol-based ligand class is developed. The binuclear titanium complex of the ligand operates through a novel mechanism allowing for the regio- and stereoselective epoxidation of primary and tertiary homoallylic alcohols (up to 98% ee), as well as first examples of 2-allylic phenols (up to 92% ee). The new catalyst system also promotes the asymmetric oxidation of gamma-hydroxypropyl sulfides giving an important class of chiral sulfoxides that have been inaccessible to date (up to 95% ee).
• Vanadium-Catalyzed Asymmetric Epoxidation of Homoallylic Alcohols
  作者：Wei Zhang、Hisashi Yamamoto

  DOI：10.1021/ja067495y

  日期：2007.1.1

  New chiral bishydroxamic acids were synthesized and tested as chiral ligands in the vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols to provide good yields and high enantioselectivities.
• Mild and stereocontrolled synthesis of iodo- and bromohydrins by halogen-tetrakis(isopropoxy)titanium opening of epoxy alcohols
  作者：Eleuterio Alvarez、Maria Teresa Nunez、Victor S. Martin

  DOI：10.1021/jo00298a002

  日期：1990.5