((2S,3S)-2-methyl-3-propyloxiran-2-yl)methanol | 153831-76-6

• 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: ((2S,3S)-2-methyl-3-propyloxiran-2-yl)methanol
• 英文别名: (2S,3S)-2,3-epoxy-2-methyl-1-hexanol；[(2S,3S)-2-methyl-3-propyloxiran-2-yl]methanol
• CAS: 153831-76-6
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: BDFUJVIXRMRZOD-BQBZGAKWSA-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：

  ((2S,3S)-2-methyl-3-propyloxiran-2-yl)methanol 在 palladium on activated charcoal 吡啶 、 咪唑 、 sodium tetrahydroborate 、 sodium azide 、 三乙基氯硅烷 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-{(R)-1-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-butyl}-benzamide
  参考文献：
  名称：

  Stereoselective production of β-amino alcohols and β-thioacyl alcohols via an application of the non-aldol aldol process

  摘要：

  The mesylates used as protecting groups to permit the formation of bis(polypropionates) via the nonaldol aldol process can be easily displaced with good nucleophiles, e.g., azide, thioacetate, acetate, to generate beta-azido (and beta-amino) alcohols, beta-thioacyl alcohols, and aldols of the opposite chirality, e.g.,syn isomers afford anti products. Thus the anti mesylate 15 affords the all-anti mzido aldol system 16 in good yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01786-4
• 作为产物：
  描述：

  2-甲基己-2-烯-1-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 作用下， 以94%的产率得到((2S,3S)-2-methyl-3-propyloxiran-2-yl)methanol
  参考文献：
  名称：

  Jung, Michael E.; D'Amico, Denn C., Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 12208 - 12209

  摘要：

  DOI：

文献信息

• Trapping of Payne rearrangement intermediates with arylselenide anions
  作者：Michael E. Jung、Daniel L. Sun

  DOI：10.1016/j.tetlet.2014.11.103

  日期：2015.6

  The intermediate epoxy alcohols prepared via a Payne rearrangement can be trapped with arylselenide anions, giving mixtures of ring-opened products. The 1-arylseleno-2,3-diols are generally favored over the 3-arylseleno-1,2-diols in this process although the reaction of trisubstituted epoxyalcohols, for example, 17, differs from those of disubstituted epoxyalcohols, for example, 21.

  通过Payne重排制备的中间体环氧醇可被芳硒化物阴离子捕获，得到开环产物的混合物。尽管三取代环氧醇（例如17）的反应不同于二取代环氧醇（例如21）的反应，但是在此方法中，1-芳基硒代2,3-二醇通常比3-芳基硒代1,2-二醇更受青睐。。
• 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 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.
• US5426206A
  申请人：——

  公开号：US5426206A

  公开（公告）日：1995-06-20