2-hydroxymethyl-3-(p-methoxybenzyloxy)prop-1-ene | 168321-27-5

• 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: 2-hydroxymethyl-3-(p-methoxybenzyloxy)prop-1-ene
• 英文别名: 2-(4-methoxybenzyloxymethyl)-prop-2-en-1-ol；2-[(4-Methoxyphenyl)methoxymethyl]prop-2-en-1-ol；2-[(4-methoxyphenyl)methoxymethyl]prop-2-en-1-ol
• CAS: 168321-27-5
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: DDOOZKLLJRLYFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-hydroxymethyl-3-(p-methoxybenzyloxy)prop-1-ene 在 咪唑 、 溴 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以85%的产率得到2-bromomethyl-3-(p-methoxybenzyloxy)prop-1-ene
  参考文献：
  名称：

  A new synthetic approach to 5-dethia-4-methyl-5-oxacephems

  摘要：

  Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00939-6
• 作为产物：
  描述：

  2-chloromethyl-3-(p-methoxybenzyloxy)prop-1-ene 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以80%的产率得到2-hydroxymethyl-3-(p-methoxybenzyloxy)prop-1-ene
  参考文献：
  名称：

  A new synthetic approach to 5-dethia-4-methyl-5-oxacephems

  摘要：

  Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00939-6

文献信息

• Synthesis and evaluation of a new class of tertiary alcohol based BACE-1 inhibitors
  作者：Francesco Russo、Fredrik Wångsell、Jonas Sävmarker、Micael Jacobsson、Mats Larhed

  DOI：10.1016/j.tet.2009.09.106

  日期：2009.11

  therapy. In accordance with the successful identification of masked inhibitors of HIV-1 protease, we envisioned that tert-alcohol containing transition-state mimicking structures would also be worthwhile evaluating as BACE-1 inhibitors. Twelve novel inhibitors were prepared via synthetic routes using epoxyalcohol derivates as key intermediates. The best synthesized tert-hydroxy inhibitor exhibited a BACE-1

  BACE-1已成为未来阿尔茨海默氏症治疗中最具特征的靶标之一。根据成功鉴定的HIV-1蛋白酶的掩蔽抑制剂，我们预见到含有叔醇的过渡态模拟结构也将作为BACE-1抑制剂值得评估。通过合成路线使用环氧醇衍生物作为关键中间体制备了十二种新型抑制剂。最佳合成的叔羟基抑制剂的BACE-1 IC 50值为0.38μM。
• Total Synthesis of Paecilomycine A
  作者：Sun-Joon Min、Samuel J. Danishefsky

  DOI：10.1002/anie.200605058

  日期：2007.3.19
• Spirodiepoxide Strategy to the C Ring of Pectenotoxin 4: Synthesis of the C1−C19 Sector
  作者：Sipak Joyasawal、Stephen D. Lotesta、N. G. Akhmedov、Lawrence J. Williams

  DOI：10.1021/ol902984e

  日期：2010.3.5

  The synthesis of a C1-C19 precursor to pectenotoxin 4 is presented, The strategy employed the functionalized allene shown. Key features include: olefin metathesis of two simple fragments to prepare the left portion of the allene-precursor, diastereoselective propargylation of an epoxy aldehyde to form the right portion, use of the DMDO-stable m-fluorobenzyl ether, and an allene spirodiepoxidation/C-ring formation cascade.
• A new synthetic approach to 5-dethia-4-methyl-5-oxacephems
  作者：Zbigniew Kałuża、Arkadiusz Kazimierski、Krzysztof Lewandowski、Kinga Suwińska、Beata Szczȩsna、Marek Chmielewski

  DOI：10.1016/s0040-4020(03)00939-6

  日期：2003.7

  Starting from (L)-ethyl lactate and 4-vinyloxy-azetidin-2-one the diastereomeric (4S,6R)- and (4S,6S)-4-methyl-5-oxa-3-methylene and 3-oxo-cephams were obtained. The formation of the cepham skeleton proceeds with a diastereomeric excess up to 80%, depending on catalyst and reaction conditions. For comparison, the corresponding racemic cephams lacking a methyl at C-4 or with a gem-dimethyl group at C-4 were synthesized. (C) 2003 Elsevier Ltd. All rights reserved.