(±)-(2-methyl-3-propyloxiran-2-yl)methanol

• 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-methyl-3-propyloxiran-2-yl)methanol
• 英文别名: (2-Methyl-3-propyloxiran-2-yl)methanol
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: BDFUJVIXRMRZOD-UHFFFAOYSA-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：

  三乙基氯硅烷 、 (±)-(2-methyl-3-propyloxiran-2-yl)methanol 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以97%的产率得到Triethyl-((2R,3R)-2-methyl-3-propyl-oxiranylmethoxy)-silane
  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-2-戊烯醛 在 sodium tetrahydroborate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (±)-(2-methyl-3-propyloxiran-2-yl)methanol
  参考文献：
  名称：

  Borinic Acid Catalyzed, Regioselective Chloroacylations and Chlorosulfonylations of 2,3-Epoxy Alcohols

  摘要：

  In the presence of a borinic acid derived catalyst, 2,3-epoxy alcohols undergo couplings with acyl and sulfonyl chlorides. This transformation directly generates O-acylated or O-sulfonylated chlorohydrin diols, with significant levels of regioselectivity for both the ring-opening and O-functionalization steps.

  DOI：

  10.1021/acs.orglett.5b01541

文献信息

• Borinic Acid Catalyzed, Regioselective Chloroacylations and Chlorosulfonylations of 2,3-Epoxy Alcohols
  作者：Kashif Tanveer、Kareem Jarrah、Mark S. Taylor

  DOI：10.1021/acs.orglett.5b01541

  日期：2015.7.17

  In the presence of a borinic acid derived catalyst, 2,3-epoxy alcohols undergo couplings with acyl and sulfonyl chlorides. This transformation directly generates O-acylated or O-sulfonylated chlorohydrin diols, with significant levels of regioselectivity for both the ring-opening and O-functionalization steps.
• 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.