methyl 4-hydroxy-5-hexynoate | 118800-10-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 4-hydroxy-5-hexynoate
• 英文别名: Methyl 4-hydroxyhex-5-ynoate
• CAS: 118800-10-5
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: OSDRMRSHBFQVJF-UHFFFAOYSA-N

物化性质

• 沸点：
  74-76 °C(Press: 0.3 Torr)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-hydroxy-5-hexynoate 在 吡啶 、 4-二甲氨基吡啶 、 氨 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 为溶剂， 反应 76.0h， 生成 1-methyl-5-(3-pyrrolidino-1-propynyl)-2-pyrrolidone
  参考文献：
  名称：

  Conformationally restricted analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide

  摘要：

  Conformationally restricted analogues of the selective partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 2) were synthesized. The compounds were tested for muscarinic and antimuscarinic activity in the isolated guinea pig ileum and in intact mice. They were found to be moderately potent muscarinic antagonists or weak partial agonists. The new compounds were less potent than 2 in inhibiting (-)-[3H]-N-methylscopolamine binding in the rate cerebral cortex. Thus, structural modifications of 2 in which part of the amide moiety has been connected with the methyl group in the butynyl chain to form a five-membered ring decrease affinity and in most cases abolish efficacy.

  DOI：

  10.1021/jm00124a022
• 作为产物：
  描述：

  丁二酸单甲酯酰氯 在 sodium tetrahydroborate 、 三氯化铝 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 methyl 4-hydroxy-5-hexynoate
  参考文献：
  名称：

  Conformationally restricted analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide

  摘要：

  Conformationally restricted analogues of the selective partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 2) were synthesized. The compounds were tested for muscarinic and antimuscarinic activity in the isolated guinea pig ileum and in intact mice. They were found to be moderately potent muscarinic antagonists or weak partial agonists. The new compounds were less potent than 2 in inhibiting (-)-[3H]-N-methylscopolamine binding in the rate cerebral cortex. Thus, structural modifications of 2 in which part of the amide moiety has been connected with the methyl group in the butynyl chain to form a five-membered ring decrease affinity and in most cases abolish efficacy.

  DOI：

  10.1021/jm00124a022

文献信息

• A New Class of Redox Isomerization of <i>N</i>-Alkylpropargylamines into <i>N</i>-Alkylideneallylamines Catalyzed by a ReBr(CO)₅/Amine <i>N</i>-oxide System
  作者：Yoshiya Fukumoto、Natsuki Okazaki、Naoto Chatani

  DOI：10.1021/acs.orglett.9b00325

  日期：2019.3.15

  N-alkylpropargylamines are converted into N-alkylideneallylamines in the presence of rhenium(I) complexes as catalysts is described. Among the additives tested, certain pyridine N-oxides and tertiary amine N-oxides were effective for the reaction to proceed, and in particular, the use of 2,6-lutidine N-oxides gave the best results. The choice of a diphenylmethyl group as a substituent on the nitrogen

  氧化还原异构化反应，其特征在于Ñ -alkylpropargylamines被转换成Ñ中铼的存在-alkylideneallylamines（I）配合物作为催化剂进行说明。在测试的添加剂中，某些吡啶N-氧化物和叔胺N-氧化物对于反应进行是有效的，特别是使用2,6-二甲基吡啶N-氧化物可获得最佳结果。选择二苯甲基作为氮原子上的取代基是反应成功的关键，使其完全完成。
• Kornilov, A. M.; Sorochinskii, A. E.; Kukhar', V. P., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 12.1, p. 2260 - 2262
  作者：Kornilov, A. M.、Sorochinskii, A. E.、Kukhar', V. P.

  DOI：——

  日期：——
• KORNILOV, A. M.;SOROCHINSKIJ, A. E.;KUXAR, V. P., ZH. ORGAN. XIMII, 25,(1989) N2, S. 2520-2523
  作者：KORNILOV, A. M.、SOROCHINSKIJ, A. E.、KUXAR, V. P.

  DOI：——

  日期：——
• LUNDKVIST, J. R. MICHAEL;RINGDAHL, BJORN;HACKSELL, ULI, J. MED. CHEM., 32,(1989) N, C. 863-869
  作者：LUNDKVIST, J. R. MICHAEL、RINGDAHL, BJORN、HACKSELL, ULI

  DOI：——

  日期：——
• Conformationally restricted analogs of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide
  作者：J. R. Michael Lundkvist、Bjorn Ringdahl、Uli Hacksell

  DOI：10.1021/jm00124a022

  日期：1989.4

  Conformationally restricted analogues of the selective partial muscarinic agonist N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM 5; 2) were synthesized. The compounds were tested for muscarinic and antimuscarinic activity in the isolated guinea pig ileum and in intact mice. They were found to be moderately potent muscarinic antagonists or weak partial agonists. The new compounds were less potent than 2 in inhibiting (-)-[3H]-N-methylscopolamine binding in the rate cerebral cortex. Thus, structural modifications of 2 in which part of the amide moiety has been connected with the methyl group in the butynyl chain to form a five-membered ring decrease affinity and in most cases abolish efficacy.