[1-Hydrazinocarbonyl-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid benzyl ester | 39978-50-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [1-Hydrazinocarbonyl-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid benzyl ester
• 英文别名: 2-(Benzyloxycarbonylamino)-3-(4-hydroxyphenyl)propionic acid hydrazide；benzyl N-[1-hydrazinyl-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 39978-50-2
• 化学式: C₁₇H₁₉N₃O₄
• 分子量: 329.356
• InChiKey: YRNMJERWBOKZEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1-Hydrazinocarbonyl-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid benzyl ester 在 四溴化碳 、 三苯基膦 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 [1-(5-tert-Butyl-[1,3,4]oxadiazol-2-yl)-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  由羧酸和酰肼轻度高效地一锅合成1,3,4-恶二唑

  摘要：

  据报道，一种方便的一锅法从酸和酰基酰肼合成2，5-二取代的1,3,4-恶二唑。用CDI进行酸活化，然后与所需的酰肼偶联，并在同一罐中用Ph 3 P和CBr 4脱水，得到相应的1,3,4-恶二唑，收率很高。给出了酸和酰肼组分的范围。

  DOI：

  10.1016/j.tetlet.2006.05.051

文献信息

• Heat-stable Enterotoxin (ST_h) of Human Enterotoxigenic<i>Escherichia coli</i>(Strain SK-1). Structure-activity Relationship
  作者：Haruo Ikemura、Hiroyuki Watanabe、Saburo Aimoto、Yasutsugu Shimonishi、Saburo Hara、Tae Takeda、Yoshifumi Takeda、Toshio Miwatani

  DOI：10.1246/bcsj.57.2550

  日期：1984.9

  For examination of the structure-activity relationship of STh, five shorter analogs of STh lacking one to five N-terminal amino acid residues of STh were synthesized. The synthetic peptides were confirmed to have the same intramolecular disulfide linkages as those in native STh. These peptides caused fluid accumulation in the intestine of suckling mice at almost the same molar levels as that of native STh. The toxicities of these peptides were also neutralized by antisera raised against native STh. These results indicated that the toxic and antigenic sites of STh are both located in the amino acid sequence between the Cys residue at the 5th position from the N-terminus and the C-terminal Tyr residue.

  为了检查STh的结构-活性关系，合成了缺少1至5个STh N端氨基酸残基的5个较短的STh类似物。合成肽被证实具有与天然 STh 相同的分子内二硫键。这些肽在乳鼠肠道中引起液体积聚，其摩尔水平几乎与天然 STh 相同。这些肽的毒性也被针对天然 STh 的抗血清中和。这些结果表明，STh的毒性和抗原位点均位于N端第5位Cys残基和C端Tyr残基之间的氨基酸序列中。
• A mild and efficient one pot synthesis of 1,3,4-oxadiazoles from carboxylic acids and acyl hydrazides
  作者：Hemaka A. Rajapakse、Hong Zhu、Mary Beth Young、Bryan T. Mott

  DOI：10.1016/j.tetlet.2006.05.051

  日期：2006.7

  A convenient one pot method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from acids and acyl hydrazides is reported. Acid activation with CDI, followed by coupling with the desired acylhydrazide and dehydration in the same pot with Ph3P and CBr4 affords the corresponding 1,3,4-oxadiazoles in good yield. The scope of the acid and acylhydrazide components is presented.

  据报道，一种方便的一锅法从酸和酰基酰肼合成2，5-二取代的1,3,4-恶二唑。用CDI进行酸活化，然后与所需的酰肼偶联，并在同一罐中用Ph 3 P和CBr 4脱水，得到相应的1,3,4-恶二唑，收率很高。给出了酸和酰肼组分的范围。