prop-2-ynyl formate | 32042-39-0

• 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: prop-2-ynyl formate
• 英文别名: 2-propynyl formate；propargyl formate；formic acid prop-2-ynyl ester；Ameisensaeure-prop-2-inylester；Ameisensaeure-propargylester；Prop-2-ynylformiat
• CAS: 32042-39-0
• 化学式: C₄H₄O₂
• 分子量: 84.0746
• InChiKey: KDIDLLIMHZHOHO-UHFFFAOYSA-N

物化性质

• 沸点：
  105-109 °C
• 密度：
  1.025±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  prop-2-ynyl formate 在 acetate buffer 、 potassium chloride 、 水 作用下， 生成 甲酸 、 2-丙炔-1-醇
  参考文献：
  名称：

  General base catalysis of ester hydrolysis

  摘要：

  The hydrolysis of alkyl formates with leaving groups in the range pK(a) = 12-16 is catalyzed by substituted acetate anions. There is an increase in the Bronsted beta value for general base catalysis with decreasing pK(a) of the leaving alcohol and a complementary increase in -beta(lg) with decreasing pK(a) of the catalyzing base, both of which are consistent with a value of p(xy) = partial derivative beta/-pK(lg) = partial derivative beta(lg)/-partial derivative pK(BH) congruent-to 0.11. This result supports a class n mechanism of general base catalysis, in which a proton is abstracted from the nucleophilic water molecule by the base catalyst in the transition state; it is not consistent with the kinetically equivalent class e mechanism of electrophilic catalysis by general acids of a reaction with hydroxide ion, by proton donation to the leaving alcohol. Solvent deuterium isotope effects in the range k(H2O)/k(D2O) = 3.6-5.3 for the buffer-independent reaction and 2.5-2.8 for catalysis by CH3COO- support concerted proton transfer and O-C bond formation. The secondary isotope effect for catalysis of the hydrolysis of LCOOMe by acetate ion is k(D)/k(H) = 1.05. Both nucleophilic and general base mechanisms of catalysis by acetate anions are observed for the hydrolysis of substituted phenyl formates with leaving groups of pK(a) = 7.1 -10.1. A small value of beta = 0.12 for general base catalysis of the hydrolysis of phenyl formate and p-methylphenyl formate represents catalysis of the addition of water by hydrogen bonding of water to the base catalyst. On the other hand, a larger value of beta = 0.35 and a decrease in k(H2O)/k(D2O) to 1.2 were observed for general base catalysis of the hydrolysis of p-nitrophenyl formate. It is suggested that the increase in beta with decreasing pK(lg) (an apparent ''anti-Hammond effect'') may be accounted for by a change in mechanism, from catalysis of a stepwise reaction of phenyl and p-methylphenyl formates to concerted general base catalysis of formyl transfer to water for the reaction of p-nitrophenyl formate.

  DOI：

  10.1021/ja00067a020
• 作为产物：
  描述：

  Hex-1-en-2-yl formate 、 2-丙炔-1-醇 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 prop-2-ynyl formate
  参考文献：
  名称：

  Neveux, Muriel; Bruneau, Christian; Dixneuf, Pierre H., Journal of the Chemical Society. Perkin transactions I, 1991, # 5, p. 1197 - 1199

  摘要：

  DOI：

文献信息

• [EN] WATER SOLUBLE ESTERS OF [N-(4-AMINO-2-BUTYNYL)] WITH ANTICANCER ACTIVITY<br/>[FR] ESTERS HYDROSOLUBLES DE [N-(4-AMINO-2-BUTYNYL)] PRESENTANT UNE ACTIVITE ANTICANCEREUSE
  申请人：SALAMA ZOSER B

  公开号：WO2005095369A1

  公开（公告）日：2005-10-13

  The present invention relates to water soluble esters of [N-(4-amino-2-butynyl)] or 4-(N-substituted amino)-2-butynyl-1-esters and methods for production of said esters and the use of the esters for treatment of cancer.

  本发明涉及[N-(4-氨基-2-丁炔基)]或4-(N-取代氨基)-2-丁炔基-1-酯的水溶性酯类化合物，以及制备该酯类化合物的方法和将其用于治疗癌症的用途。
• 919. Physical properties and chemical constitution. Part XXIX. Acetylenic compounds
  作者：Roman Grzeskowiak、George H. Jeffery、Arthur I. Vogel

  DOI：10.1039/jr9600004719

  日期：——
• Carlson, Charles G.; Hall, Judith E.; Huang, Yan Y., Canadian Journal of Chemistry, 1987, vol. 65, p. 2461 - 2463
  作者：Carlson, Charles G.、Hall, Judith E.、Huang, Yan Y.、Kotila, Sirpa、Rauk, Arvi、Tavares, Donald F.

  DOI：——

  日期：——
• WO2008/9315
  申请人：——

  公开号：——

  公开（公告）日：——
• New Compounds. Some Acetylenic Compounds
  作者：C D. Heaton、C R. Noller

  DOI：10.1021/ja01176a601

  日期：1949.8