(E)-3-(4-Allyloxy-3-methoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6R)-6-[2-(4-allyloxy-phenyl)-ethoxy]-4,5-bis-(2-chloro-acetoxy)-2-(2-chloro-acetoxymethyl)-tetrahydro-pyran-3-yl ester | 190123-33-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(4-Allyloxy-3-methoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6R)-6-[2-(4-allyloxy-phenyl)-ethoxy]-4,5-bis-(2-chloro-acetoxy)-2-(2-chloro-acetoxymethyl)-tetrahydro-pyran-3-yl ester
• CAS: 190123-33-2
• 化学式: C₃₆H₃₉Cl₃O₁₃
• 分子量: 786.057
• InChiKey: JSWDKLMWZACJDW-PNTAZIKESA-N

物化性质

• 沸点：
  786.651±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.355±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  52.0
• 可旋转键数：
  21.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  151.35
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-Allyloxy-3-methoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6R)-6-[2-(4-allyloxy-phenyl)-ethoxy]-4,5-bis-(2-chloro-acetoxy)-2-(2-chloro-acetoxymethyl)-tetrahydro-pyran-3-yl ester 在 氨 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 1.5h， 生成 2-(3-methoxy-4-allyloxyphenyl)ethyl-4-Ο-(E)-4-Allyloxycaffeoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of the phenylpropanoid glycoside, grayanoside A

  摘要：

  Grayanoside A, 2-(4-hydroxyphenyl)ethyl 6-O-feruloyl-beta-D-glucopyranoside, was synthesized for the first time by using chloroacetyl groups for the protection of hydroxy functions. 2-(4-Allyloxyphenyl)ethyl 4-O-[(4-O-allyl)feruloyl]-2,3,6-tri-O-chloroacetyl-beta-D-glucopyranoside (12) was synthesized from 2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-beta-D-glucopyranoside (8) in four steps with the goal of preparing syringalide B. It was found, however, that the feruloyl group migrated from the 4- to the 6-position of the glycopyranoside during the deprotection of 12. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00032-3
• 作为产物：
  描述：

  2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 (E)-3-(4-Allyloxy-3-methoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6R)-6-[2-(4-allyloxy-phenyl)-ethoxy]-4,5-bis-(2-chloro-acetoxy)-2-(2-chloro-acetoxymethyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Total synthesis of the phenylpropanoid glycoside, grayanoside A

  摘要：

  Grayanoside A, 2-(4-hydroxyphenyl)ethyl 6-O-feruloyl-beta-D-glucopyranoside, was synthesized for the first time by using chloroacetyl groups for the protection of hydroxy functions. 2-(4-Allyloxyphenyl)ethyl 4-O-[(4-O-allyl)feruloyl]-2,3,6-tri-O-chloroacetyl-beta-D-glucopyranoside (12) was synthesized from 2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-beta-D-glucopyranoside (8) in four steps with the goal of preparing syringalide B. It was found, however, that the feruloyl group migrated from the 4- to the 6-position of the glycopyranoside during the deprotection of 12. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00032-3