1-(4-(benzyloxy)-3-methoxyphenyl)prop-2-en-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-(benzyloxy)-3-methoxyphenyl)prop-2-en-1-ol
• 英文别名: 1-(3-Methoxy-4-phenylmethoxyphenyl)prop-2-en-1-ol
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: GQRJBQXCSZAOHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-(4-(benzyloxy)-3-methoxyphenyl)prop-2-en-1-ol 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以87%的产率得到1-(3-methoxy-4-(benzyloxy)phenyl)-2,3-epoxypropan-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of Polysubstituted Tetrahydrofurans by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source. Application to the Total Synthesis of (±)-Methylenolactocin and (±)-Protolichesterinic Acid

  摘要：

  Radical cyclization reactions of substituted alpha-(prop-2-ynyloxy) epoxides using bis(cyclopentadienyl)-titanium(III) chloride as the radical source resulted in polysubstituted tetrahydrofurans. Titanium(III) species were prepared in situ from commercially available titanocene dichloride and zinc dust in tetrahydrofuran, Upon radical cyclization, 2-aryl epoxides 3a-e afforded only trans products 4a-e whereas the 2-alkyl epoxides 3f-h formed a mixture of isomeric products 4f-h in a ratio of 5:1. Some of the aryl tetrahydrofuran derivatives have already been used for the synthesis of bioactive furofuran lignans. 2-Pentyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4f) and 2-tridecyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4g) have been transformed to two antitumor antibiotics (+/-)-methylenolactocin (1f) and (+/-)-protolichesterinic acid (1g), respectively, in good overall yield.

  DOI：

  10.1021/jo971526d
• 作为产物：
  描述：

  香草醛 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-(4-(benzyloxy)-3-methoxyphenyl)prop-2-en-1-ol
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure Lignin Dimer Models for Catalytic Selectivity Studies

  摘要：

  A series of highly enantioselective transformations, such as the Sharpless asymmetric epoxidation and Jacobsen hydrolytic kinetic resolution, were utilized to achieve the complete stereoselective synthesis of beta-O-4 lignin dimer models containing the S, G, and H subunits with excellent ee (>99%) and moderate to high yields. This unprecedented synthetic method can be exploited for enzymatic, microbial, and chemical investigations into lignins degradation and depolymerization as related to its stereochemical constitution. Preliminary degradation studies using enantiopure Co(salen) catalysts are also reported.

  DOI：

  10.1021/jo502685k

文献信息

• Total Synthesis and Stereochemical Confirmation of (−)-Olivil, (+)-Cycloolivil, (−)-Alashinols F and G, (+)-Cephafortin A, and Their Congeners: Filling in Biosynthetic Gaps
  作者：Jithender Reddy Vakiti、Stephen Hanessian

  DOI：10.1021/acs.orglett.0c00773

  日期：2020.5.1

  For the first time, we describe the stereocontrolled total syntheses of olivil, cephafortin A, 4-des-O-methyl-4-O-rhamnosyl cephafortin A, and alashinol F from a common precursor using a combination of chemoenzymatic and biomimetic methods for the systematic introduction of functional groups on three vicinal stereogenic carbon atoms. We revised the previously assigned stereochemistry of (+)-cephafortin

  我们首次描述了使用化学酶法和仿生方法相结合，从共同前体中立体控制全合成 olivil、头孢福汀 A、4-des-O-甲基-4-O-鼠李糖基头孢福汀 A 和 alashinol F。在三个邻位立体碳原子上系统地引入官能团。我们修改了之前指定的 (+)-头孢福汀 A 的立体化学，将其报告为对映体。天然和非自然同系物提供了对该家族成员的生物遗传相互关系的见解。
• Synthesis of (±)-5′-methoxyhydnocarpin-D, an inhibitor of the Staphylococcus aureus multidrug resistance pump
  作者：Kin-Fai Chan、Yunzhe Zhao、Larry M.C. Chow、Tak Hang Chan

  DOI：10.1016/j.tet.2005.02.024

  日期：2005.4

  The total synthesis of regioisomerically pure (+/-)-5'-methoxyhydnocarpin-D (6) from commercially available vanillin (7), methyl gallate (9) and 2',4',6'-trihydroxyaceophenone (10) is achieved. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of Enantiomerically Pure Lignin Dimer Models for Catalytic Selectivity Studies
  作者：Costyl N. Njiojob、Jennifer L. Rhinehart、Joseph J. Bozell、Brian K. Long

  DOI：10.1021/jo502685k

  日期：2015.2.6

  A series of highly enantioselective transformations, such as the Sharpless asymmetric epoxidation and Jacobsen hydrolytic kinetic resolution, were utilized to achieve the complete stereoselective synthesis of beta-O-4 lignin dimer models containing the S, G, and H subunits with excellent ee (>99%) and moderate to high yields. This unprecedented synthetic method can be exploited for enzymatic, microbial, and chemical investigations into lignins degradation and depolymerization as related to its stereochemical constitution. Preliminary degradation studies using enantiopure Co(salen) catalysts are also reported.
• Stereoselective Synthesis of Polysubstituted Tetrahydrofurans by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source. Application to the Total Synthesis of (±)-Methylenolactocin and (±)-Protolichesterinic Acid
  作者：Pijus Kumar Mandal、Gourhari Maiti、Subhas Chandra Roy

  DOI：10.1021/jo971526d

  日期：1998.5.1

  Radical cyclization reactions of substituted alpha-(prop-2-ynyloxy) epoxides using bis(cyclopentadienyl)-titanium(III) chloride as the radical source resulted in polysubstituted tetrahydrofurans. Titanium(III) species were prepared in situ from commercially available titanocene dichloride and zinc dust in tetrahydrofuran, Upon radical cyclization, 2-aryl epoxides 3a-e afforded only trans products 4a-e whereas the 2-alkyl epoxides 3f-h formed a mixture of isomeric products 4f-h in a ratio of 5:1. Some of the aryl tetrahydrofuran derivatives have already been used for the synthesis of bioactive furofuran lignans. 2-Pentyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4f) and 2-tridecyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4g) have been transformed to two antitumor antibiotics (+/-)-methylenolactocin (1f) and (+/-)-protolichesterinic acid (1g), respectively, in good overall yield.
• Racemic synthesis of Linderuca C from lignin derived starting materials
  作者：Daniel J. Davidson、Oliver Lynard、Daniel M. Miles-Barrett、Geraud N. Sansom、Filomena Tedesco、Fraser Watson、Nicholas J. Westwood

  DOI：10.24820/ark.5550190.p012.087

  日期：——