(1S)-1-[(2S,3S)-3-[2-[(4-methoxyphenyl)methoxy]ethyl]oxiran-2-yl]ethanol | 671232-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S)-1-[(2S,3S)-3-[2-[(4-methoxyphenyl)methoxy]ethyl]oxiran-2-yl]ethanol
• CAS: 671232-59-0
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: SEJKRCJWKGESDG-BPNCWPANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(2S,3S)-3-[2-[(4-methoxyphenyl)methoxy]ethyl]oxiran-2-yl]ethanol 在 2,6-二甲基吡啶 、 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 草酰氯 、 二甲基亚砜 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 1.0h， 生成 (4R,5S,E)-5-(tert-butyl-dimethylsilyloxy)-4-hydroxy-hex-2-en-1-al
  参考文献：
  名称：

  Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A

  摘要：

  An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transformed into the functionalised carboxylic acid 5, an advanced stage intermediate from which the total synthesis of macrosphelide A has been reported. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.070
• 作为产物：
  描述：

  (E)-5-(4-methoxy-benzyloxy)-pent-2-en-1-al 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1S)-1-[(2S,3S)-3-[2-[(4-methoxyphenyl)methoxy]ethyl]oxiran-2-yl]ethanol
  参考文献：
  名称：

  Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: application in the formal synthesis of macrosphelide A

  摘要：

  An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transformed into the functionalised carboxylic acid 5, an advanced stage intermediate from which the total synthesis of macrosphelide A has been reported. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.070

文献信息

• Synthesis of chiral 1,3-diols by radical-mediated regioselective opening of 2,3-epoxy alcohols using cp2TiCl
  作者：Tushar K Chakraborty、Sanjib Das

  DOI：10.1016/s0040-4039(02)00241-1

  日期：2002.3

  Radical-mediated opening of chiral 2,3-epoxy alcohols la-e, regioselectively at the 2-position, using cp(2)TiCl in the absence of a hydrogen source leads to the formation of the 1,3-diols 2a-e. (C) 2002 Published by Elsevier Science Ltd.