Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester | 748154-82-7

• 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: Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester
• 英文别名: [(1R,5S)-5-[(4-methoxyphenyl)methoxy]-2-oxocyclohex-3-en-1-yl] 2-bromoacetate
• CAS: 748154-82-7
• 化学式: C₁₆H₁₇BrO₅
• 分子量: 369.212
• InChiKey: VVCYAFNJRZAILP-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester 在 silver trifluoromethanesulfonate 、 sodium hydride 、 silver carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (-)-(6S,7aR)-6-(2',3',4',5'-tetra-O-acetyl-β-D-glucopyranosyl)oxy-7,7a-dihydrobenzofuran-2(4H)-one
  参考文献：
  名称：

  Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

  摘要：

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.129
• 作为产物：
  描述：

  methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 吡啶 、 咪唑 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 水 、 碘 、 mercury(II) trifluoroacetate 、 sodium hydride 、 溶剂黄146 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 生成 Bromo-acetic acid (1R,5S)-5-(4-methoxy-benzyloxy)-2-oxo-cyclohex-3-enyl ester
  参考文献：
  名称：

  Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

  摘要：

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.129

文献信息

• Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes
  作者：Yoshifumi Urakawa、Takanori Sugimoto、Hirotaka Sato、Minoru Ueda

  DOI：10.1016/j.tetlet.2004.05.129

  日期：2004.7

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.