(E)-6-(4-Methoxy-benzyloxy)-hex-3-en-2-ol | 671232-58-9

• 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: (E)-6-(4-Methoxy-benzyloxy)-hex-3-en-2-ol
• 英文别名: (E)-6-[(4-methoxyphenyl)methoxy]hex-3-en-2-ol
• CAS: 671232-58-9
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: OGLGCAZSKHQWQT-HWKANZROSA-N

物化性质

• 沸点：
  358.3±42.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-6-(4-Methoxy-benzyloxy)-hex-3-en-2-ol 在 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 草酰氯 、 L-(+)-酒石酸二乙酯 、 4 A molecular sieve 、 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-methoxybenzyloxy)pent-2-en-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (E)-6-(4-Methoxy-benzyloxy)-hex-3-en-2-ol
  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

• Regio- and stereoselective SN2′ reaction of an allylic picolinate in the synthesis of LY426965
  作者：Yuichi Kobayashi、Kai Yamaguchi、Masao Morita

  DOI：10.1016/j.tet.2018.02.045

  日期：2018.4

  applied to the synthesis of LY426965. Reduction of (R)-6-(PMB-oxy)-3-hexyn-2-ol of 93% ee (PMB = p-MeOC6H4CH2) using Red-Al gave (R,Z)-4-iodo-5-(PMB-oxy)hex-3-en-2-ol, which was later converted to the Me-substituted allylic picolinate by Pd-catalyzed coupling with MeZnI followed by esterification with picolinic acid. Allylic substitution with PhMgBr/Cu(acac)2 proceeded with high anti SN2′ selectivity

  用基于ArMgBr的铜试剂对γ，γ-二取代的第二级烯丙基吡啶甲酸二甲酯进行烯丙基取代，从而合成LY426965。使用Red-Al还原93％ee（PMB = p -MeOC 6 H 4 CH 2）的（R）-6-（PMB-oxy）-3-hexyn-2-ol 得到（R，Z）-4-碘-5-（PMB-氧基）己-3-烯-2-醇，其随后通过与MeZnI的Pd催化偶合，然后用吡啶甲酸酯化，转化为Me-取代的烯丙基吡啶甲酸酯。用PhMgBr / Cu（acac）2进行烯丙基取代具有很高的抗S N 2'选择性（99％）。臭氧分解，添加c-Hex-MgBr生成醛，并用哌嗪衍生物进行还原胺化，得到LY426965。
• 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
  作者：Tushar K Chakraborty、Subhas Purkait、Sanjib Das

  DOI：10.1016/j.tet.2003.09.070

  日期：2003.11

  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.