2-叔丁氧基-4-戊炔 | 163631-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-叔丁氧基-4-戊炔
• 英文名称: 2-tert-butoxy-4-pentyne
• 英文别名: 2-t-Butoxy-4-pentyne；4-[(2-methylpropan-2-yl)oxy]pent-1-yne
• CAS: 163631-23-0
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: VSZAJRNHKHNXPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-叔丁氧基-4-戊炔 在 palladium on activated charcoal 、 Ru-carbon copper(I) chloride 、 正丁基锂 、 jones reagent 、 四溴化碳 、 盐酸羟胺 、 氢气 、 对甲苯磺酸 、 叔丁胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 乙醇 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 32.0h， 生成 11-羟基十二碳-3-炔酸
  参考文献：
  名称：

  Pheromones of Coleoptera

  摘要：

  A ten-step synthesis of a racemic form of 3(Z),11(S)-dodecen-11-olide (ferrulactone II) has been developed. The synthesis is based on the Cadiot-Chodkiewicz cross-coupling of 4-pentyn-2-ol with 2-propyn-1-ol followed by carbon chain elongation by 3-butyn-1-ol and gives the target lactone in 9.7 % overall yield (based on the starting pentynol). Air of the three building blocks used for the chain assembly are easily accessible from acetylene. The protection of OH groups as tert-butyl ethers has certain synthetic advantages.

  DOI：

  10.1007/bf00698893
• 作为产物：
  描述：

  4-戊炔-2-醇 、 异丁烯 在 Amberlyst H-15 resin 作用下， 以 正己烷 为溶剂， 反应 18.0h， 以95%的产率得到2-叔丁氧基-4-戊炔
  参考文献：
  名称：

  Pheromones of Coleoptera

  摘要：

  A ten-step synthesis of a racemic form of 3(Z),11(S)-dodecen-11-olide (ferrulactone II) has been developed. The synthesis is based on the Cadiot-Chodkiewicz cross-coupling of 4-pentyn-2-ol with 2-propyn-1-ol followed by carbon chain elongation by 3-butyn-1-ol and gives the target lactone in 9.7 % overall yield (based on the starting pentynol). Air of the three building blocks used for the chain assembly are easily accessible from acetylene. The protection of OH groups as tert-butyl ethers has certain synthetic advantages.

  DOI：

  10.1007/bf00698893

文献信息

• Functionalized N-propargylanabazine derivatives
  作者：M. V. Mavrov、S. G. Zlotin

  DOI：10.1007/s11172-009-0262-5

  日期：2009.9

  N-Propargyl derivatives of the alkaloid anabazine with carbonyl, ester, and cyano groups in the side chain were obtained by three-component condensation of anabazine hydrochloride with paraformaldehyde and appropriate terminal alkynes. Decyanoethylation and hydration of the isopropylidene double bond resulted in mono-and dihydroxy derivatives of N-propargyl-anabazines, respectively.

  通过将盐酸安乃近与多聚甲醛和适当的末端炔烃进行三组份缩合，得到了侧链中含有羰基、酯基和氰基的生物碱安乃近的 N-丙炔基衍生物。异亚丙基双键的脱氰基乙基化和水合作用分别产生了 N-丙炔基安乃近的单羟基和二羟基衍生物。
• Pheromones of Coleoptera
  作者：M. V. Mavrov、E. P. Serebryakov

  DOI：10.1007/bf00698893

  日期：1993.12

  A ten-step synthesis of a racemic form of 3(Z),11(S)-dodecen-11-olide (ferrulactone II) has been developed. The synthesis is based on the Cadiot-Chodkiewicz cross-coupling of 4-pentyn-2-ol with 2-propyn-1-ol followed by carbon chain elongation by 3-butyn-1-ol and gives the target lactone in 9.7 % overall yield (based on the starting pentynol). Air of the three building blocks used for the chain assembly are easily accessible from acetylene. The protection of OH groups as tert-butyl ethers has certain synthetic advantages.