(E)-3-[4-(2-chloroacetyl)oxy-3-methoxyphenyl]prop-2-enoic acid | 190122-81-7

• 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-(2-chloroacetyl)oxy-3-methoxyphenyl]prop-2-enoic acid
• CAS: 190122-81-7
• 化学式: C₁₂H₁₁ClO₅
• 分子量: 270.669
• InChiKey: UVSXVWBAVXGHGJ-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-[4-(2-chloroacetyl)oxy-3-methoxyphenyl]prop-2-enoic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 0.83h， 以93%的产率得到[4-[(E)-3-chloro-3-oxoprop-1-enyl]-2-methoxyphenyl] 2-chloroacetate
  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：

  阿魏酸 、 氯乙酰氯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.05h， 以75.3%的产率得到(E)-3-[4-(2-chloroacetyl)oxy-3-methoxyphenyl]prop-2-enoic acid
  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

文献信息

• Total synthesis of the phenylpropanoid glycoside, grayanoside A
  作者：San-Qi Zhang、Zhong-Jun Li、An-Bang Wang、Meng-Shen Cai、Rui Feng

  DOI：10.1016/s0008-6215(97)00032-3

  日期：1997.4

  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.