3,4-Methylendioxy-styryl-isocyanat | 24186-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3,4-Methylendioxy-styryl-isocyanat
• 英文别名: 5-[(E)-2-isocyanatoethenyl]-1,3-benzodioxole
• CAS: 24186-49-0
• 化学式: C₁₀H₇NO₃
• 分子量: 189.17
• InChiKey: OBMOBLJVUHOVBE-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-Methylendioxy-styryl-isocyanat 在 三乙基硅烷 作用下， 以 三氟乙酸 为溶剂， 反应 0.5h， 生成 ethyl (2-(benzo[d][1,3]dioxol-5-yl)ethyl)carbamate
  参考文献：
  名称：

  Regioselective cationic reduction of 2-aryl-1-N-(ethoxycarbonyl)enamines to 2-arylethylamine carbamates

  摘要：

  2-Aryl-1-N-carboalkoxyenamines (enamides) are selectively reduced to the corresponding 2-arylethylamine carbamates by Et3SiH in the presence of CF3COOH in excellent yields. The reduction proceeds by addition of hydride at C-1 and the rate-limiting step involves proton transfer from CF3COOH. This reduction is useful for preparation of isotopically labeled arylethylamines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01780-4
• 作为产物：
  描述：

  (E)-3-(1,3-benzodioxol-5-yl)acryloyl chloride 在 sodium azide 作用下， 以 水 、 甲苯 为溶剂， 反应 2.0h， 生成 3,4-Methylendioxy-styryl-isocyanat
  参考文献：
  名称：

  Synthesis and evaluation of ureido and vinylureidopenicillins as inhibitors of intraruminal lactic acid production

  摘要：

  A series of 14 vinylureidopenicillins and a series of 9 ureidopenicillins were prepared by reaction of 6-aminopenicillanic acid with vinyl isocyanates and isocyanates. These compounds were evaluated for their potential to protect ruminants against lactic acidosis. The compounds were tested for inhibition of in vitro ruminal lactic and propionic acid production, and six compounds inhibited lactic acid production to less than 10% of control at doses of 0.31 microgram/mL or lower, whereas they did not inhibit propionic acid production at doses greater than 10 micrograms/mL. The most active compounds also were screened for general antibacterial activity and were found to be weakly active against Gram-positive bacteria. The structure--activity relationships are discussed for both series. Triethylammonium 6-[3[2-(4-tert-butylphenyl)vinyl]ureido]penicillanate (4) was chosen for evaluation as an inhibitor of intraruminal lactic acidosis in vivo.

  DOI：

  10.1021/jm00142a024

文献信息

• Synthesis and evaluation of ureido and vinylureidopenicillins as inhibitors of intraruminal lactic acid production
  作者：Robin D. Clark、Joan M. Caroon、Ian T. Harrison、Arthur F. Kluge、Stefan H. Unger、Howard R. Spires、Thomas R. Mathews

  DOI：10.1021/jm00142a024

  日期：1981.10

  A series of 14 vinylureidopenicillins and a series of 9 ureidopenicillins were prepared by reaction of 6-aminopenicillanic acid with vinyl isocyanates and isocyanates. These compounds were evaluated for their potential to protect ruminants against lactic acidosis. The compounds were tested for inhibition of in vitro ruminal lactic and propionic acid production, and six compounds inhibited lactic acid production to less than 10% of control at doses of 0.31 microgram/mL or lower, whereas they did not inhibit propionic acid production at doses greater than 10 micrograms/mL. The most active compounds also were screened for general antibacterial activity and were found to be weakly active against Gram-positive bacteria. The structure--activity relationships are discussed for both series. Triethylammonium 6-[3[2-(4-tert-butylphenyl)vinyl]ureido]penicillanate (4) was chosen for evaluation as an inhibitor of intraruminal lactic acidosis in vivo.
• Regioselective cationic reduction of 2-aryl-1-N-(ethoxycarbonyl)enamines to 2-arylethylamine carbamates
  作者：Makoto N Masuno、Tadeusz F Molinski

  DOI：10.1016/s0040-4039(01)01780-4

  日期：2001.11

  2-Aryl-1-N-carboalkoxyenamines (enamides) are selectively reduced to the corresponding 2-arylethylamine carbamates by Et3SiH in the presence of CF3COOH in excellent yields. The reduction proceeds by addition of hydride at C-1 and the rate-limiting step involves proton transfer from CF3COOH. This reduction is useful for preparation of isotopically labeled arylethylamines. (C) 2001 Elsevier Science Ltd. All rights reserved.