(2R,3R)-2,3-epoxy-2-methyl-1-hexanol | 153762-82-4

• 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: (2R,3R)-2,3-epoxy-2-methyl-1-hexanol
• 英文别名: (2R,3R)-2-Methyl-3-propyloxiranemethanol；[(2R,3R)-2-methyl-3-propyloxiran-2-yl]methanol
• CAS: 153762-82-4
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: BDFUJVIXRMRZOD-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  3
• 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：

  三乙基硅基三氟甲磺酸酯 、 (2R,3R)-2,3-epoxy-2-methyl-1-hexanol 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以100%的产率得到(2S,3R)-3-(Triethylsilyloxy)-2-methylhexanal
  参考文献：
  名称：

  Stereospecific Formation of Optically Active 5-Alkyl-4-methyl-3-[(trialkylsilyl)oxy]-2-([(trialkylsilyl)oxy]- methyl)tetrahydrofurans via Diastereoselective Epoxidation and Rearrangement of 5-[(Trialkylsilyl)oxy]-2-alken-1-ols¹

  摘要：

  A novel method for the synthesis of a series of silyl ethers of 3-(silyloxy)tetrahydrofuran-2-methanols bearing substituents at all four carbon atoms of the ring has been developed. The process involves first non-aldol aldol reaction of the epoxy silyl ether 8 to give the anti aldol product 9, stereoselective olefination and reduction to the (E)- and (Z)-allylic alcohols 10 and 11, diastereoselective epoxidation of these alcohols to give any of the four diastereomeric epoxy alcohols 12-15, silylation of the alcohols to give the epoxy silyl ethers 27-30, and final Lewis acid catalyzed rearrangement of the epoxy silyl ethers to give the desired products 31-33 and 36. In the first three instances, good yields of the desired 3-(silyloxy)-2-((silyloxy)methyl)tetrahydrofurans were obtained. However, rearrangement of the epoxy silyl ether 27 gave a mixture of products, the bis-silyl ether 36 as well as the products of a second non-aldol aldol process. This hydride migration to give the 3,5-bis((trialkylsilyl)oxy)-2,4-dimethylalkanal 35 or its internally protected 1-(silyloxy)pyran 38 can be made to occur in good yield.

  DOI：

  10.1021/ja972507o
• 作为产物：
  描述：

  2-甲基己-2-烯-1-醇 以94%的产率得到(2R,3R)-2,3-epoxy-2-methyl-1-hexanol
  参考文献：
  名称：

  Stereospecific synthesis of aldols

  摘要：

  提供了一种方法，用于制备所有四种2-烷基-3-羟基烷醛、2-烷基-3-硅氧烷醛等的二对映异构体，具有高对映选择性，使用非醛缩合化学方法。合成方法还提供了新颖的、立体特异的聚丙烯酸酯和手性的2-取代-1,3-二醇的途径。

  公开号：

  US05426206A1

文献信息

• Eu(OTf)₃-Catalyzed Highly Regioselective Nucleophilic Ring Opening of 2,3-Epoxy Alcohols: An Efficient Entry to 3-Substituted 1,2-Diol Derivatives
  作者：Shun-ichiro Uesugi、Tsubasa Watanabe、Takamichi Imaizumi、Masatoshi Shibuya、Naoki Kanoh、Yoshiharu Iwabuchi

  DOI：10.1021/ol502264y

  日期：2014.9.5

  In our study of the total synthesis of (+)-irciniastatin A, we found a need to develop a method that enables a C3-selective nucleophilic ring opening of 2,3-epoxy alcohol by MeOH, by which we found that the use of combined catalytic amounts of Eu(OTf)3 and 2,6-di-tert-butyl-4-methylpyridine (DTBMP) enables the intended transformation to obtain 3-methoxy-1,2-diol efficiently. Promising features of a

  在我们对（+）-irciniastatin A的总合成的研究中，我们发现有必要开发一种方法，该方法能够使MeOH对2,3-环氧醇进行C3选择性亲核开环，从而发现使用Eu（OTf）3和2,6-二叔丁基-4-甲基吡啶（DTBMP）的组合催化量能够实现预期的转化，从而有效地获得3-甲氧基-1,2-二醇。描述了使用包括醇，硫醇和未保护的胺在内的各种亲核试剂实现2,3-和3,4-环氧醇的高度区域选择性亲核开环的方案的有前景的特征。
• Stereospecific synthesis of aldols
  申请人：The Regents of the University of California

  公开号：US05426206A1

  公开（公告）日：1995-06-20

  Methods are provided for preparing all four diastereomers of 2-alkyl-3-hydroxyalkanals, 2-alkyl-3-silyloxyalkanals, and the like, with high enantiocontrol, using non-aldol chemistry. The synthetic methods also provide novel, stereospecific routes to polypropinates and chiral 2-substituted-1,3 diols.

  提供了一种方法，用于制备所有四种2-烷基-3-羟基烷醛、2-烷基-3-硅氧烷醛等的二对映异构体，具有高对映选择性，使用非醛缩合化学方法。合成方法还提供了新颖的、立体特异的聚丙烯酸酯和手性的2-取代-1,3-二醇的途径。
• US5426206A
  申请人：——

  公开号：US5426206A

  公开（公告）日：1995-06-20
• Stereospecific Formation of Optically Active 5-Alkyl-4-methyl-3-[(trialkylsilyl)oxy]-2-([(trialkylsilyl)oxy]- methyl)tetrahydrofurans via Diastereoselective Epoxidation and Rearrangement of 5-[(Trialkylsilyl)oxy]-2-alken-1-ols¹
  作者：Michael E. Jung、Derin C. D'Amico

  DOI：10.1021/ja972507o

  日期：1997.12.17

  A novel method for the synthesis of a series of silyl ethers of 3-(silyloxy)tetrahydrofuran-2-methanols bearing substituents at all four carbon atoms of the ring has been developed. The process involves first non-aldol aldol reaction of the epoxy silyl ether 8 to give the anti aldol product 9, stereoselective olefination and reduction to the (E)- and (Z)-allylic alcohols 10 and 11, diastereoselective epoxidation of these alcohols to give any of the four diastereomeric epoxy alcohols 12-15, silylation of the alcohols to give the epoxy silyl ethers 27-30, and final Lewis acid catalyzed rearrangement of the epoxy silyl ethers to give the desired products 31-33 and 36. In the first three instances, good yields of the desired 3-(silyloxy)-2-((silyloxy)methyl)tetrahydrofurans were obtained. However, rearrangement of the epoxy silyl ether 27 gave a mixture of products, the bis-silyl ether 36 as well as the products of a second non-aldol aldol process. This hydride migration to give the 3,5-bis((trialkylsilyl)oxy)-2,4-dimethylalkanal 35 or its internally protected 1-(silyloxy)pyran 38 can be made to occur in good yield.
• Jung, Michael E.; D'Amico, Denn C., Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 12208 - 12209
  作者：Jung, Michael E.、D'Amico, Denn C.

  DOI：——

  日期：——