4-Acetoxy-4-methyl-pentin-(1) | 16169-76-9

• 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: 4-Acetoxy-4-methyl-pentin-(1)
• 英文别名: 2-Methylpent-4-yn-2-yl acetate
• CAS: 16169-76-9
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: AQHPXXFEOINLOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  60 °C(Press: 62 Torr)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  4-Acetoxy-4-methyl-pentin-(1) 在 二(三苯基膦)环戊二烯基氯化钌(II) N-甲基吗啉 、 lithium hydroxide 、 ammonium hexafluorophosphate 、 四氧化锇 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 73.0h， 生成 3-甲基-2-(3-甲基-2-丁烯基)呋喃
  参考文献：
  名称：

  A Practical Synthesis of Rosefuran. Furans from Acetylenes and Allyl Alcohols

  摘要：

  A new atom-economical synthetic strategy for the synthesis of furans emerges from beta,gamma-unsaturated ketones which are readily available from acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans are available in two steps from allyl alcohols and acetylenes with only water as the byproduct. A straightforward synthesis of the prized fragrance of oil of rose, rosefuran, from propargyl bromide, acetone, and 1-buten-3-ol in 23% overall yield illustrates the utility of this new strategy.

  DOI：

  10.1021/jo00084a026
• 作为产物：
  描述：

  2-甲基-4-戊炔-2-醇 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-Acetoxy-4-methyl-pentin-(1)
  参考文献：
  名称：

  通过α-亚氨基铑卡宾酸酯的形成引发的乙酰氧基的1，3-迁移来合成环丙烷。

  摘要：

  通过α-亚氨基铑卡宾烯引发的酰氧基的1,3-迁移，实现了一种新型的高效合成环丙烷的方法。出色的化学选择性确保了常见官能团的广泛相容性。诸如易于获得的底物，温和的反应条件和省时的工艺等优点使这种转化成为合成多功能环丙烷的有吸引力的替代策略。介绍了对该机制的初步研究和讨论。

  DOI：

  10.1021/acs.orglett.0c01764

文献信息

• Synthesis of Cyclopropanes via 1,3-Migration of Acyloxy Groups Triggered by Formation of α-Imino Rhodium Carbenes
  作者：Ze-Feng Xu、Jincheng Liu、Xin Chang、Tao Chen、Huaping Xu、Shengguo Duan、Chuan-Ying Li

  DOI：10.1021/acs.orglett.0c01764

  日期：2020.7.2

  A novel and highly efficient synthetic approach to cyclopropanes was realized via 1,3-migration of acyloxy groups triggered by α-imino rhodium carbenes. Excellent chemoselectivity ensured broad compatibility of common functional groups. Merits such as readily available substrates, mild reaction conditions, and time-saving processes qualified this transformation as an attractive alternative strategy

  通过α-亚氨基铑卡宾烯引发的酰氧基的1,3-迁移，实现了一种新型的高效合成环丙烷的方法。出色的化学选择性确保了常见官能团的广泛相容性。诸如易于获得的底物，温和的反应条件和省时的工艺等优点使这种转化成为合成多功能环丙烷的有吸引力的替代策略。介绍了对该机制的初步研究和讨论。
• A Practical Synthesis of Rosefuran. Furans from Acetylenes and Allyl Alcohols
  作者：Barry M. Trost、John A. Flygare

  DOI：10.1021/jo00084a026

  日期：1994.3

  A new atom-economical synthetic strategy for the synthesis of furans emerges from beta,gamma-unsaturated ketones which are readily available from acetylenes and allyl alcohols by simple additions in the presence of a ruthenium catalyst. Dihydroxylation using catalytic osmium tetraoxide creates a diol that is remarkably prone to cyclize to furans in the presence of an acid catalyst. The novelty of this synthesis lies in the overall strategy whereby furans are available in two steps from allyl alcohols and acetylenes with only water as the byproduct. A straightforward synthesis of the prized fragrance of oil of rose, rosefuran, from propargyl bromide, acetone, and 1-buten-3-ol in 23% overall yield illustrates the utility of this new strategy.