3-isopropyl-6-methyltetrahydro-2H-pyran-2-one | 21722-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-isopropyl-6-methyltetrahydro-2H-pyran-2-one
• 英文别名: 3-isopropyl-6-methyl-tetrahydro-pyran-2-one；3-Isopropyl-6-methyl-tetrahydro-pyran-2-on；6-Methyl-3-propan-2-yloxan-2-one
• CAS: 21722-34-9
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: ZGGSUJMJDJHZNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  112-115 °C(Press: 8 Torr)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-Methylhept-5-en-2-yl carbonochloridate 在 吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 3-isopropyl-6-methyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of .gamma.- and .delta.-lactones by free-radical annelation of Se-phenyl selenocarbonates

  摘要：

  A general method for the synthesis of gamma- and delta-lactones through the intramolecular addition of alkoxycarbonyl radicals, formed by reaction of Se-phenylselenocarbonates with n-Bu3SnH, onto carbon-carbon multiple bonds is described. This free-radical cyclization is characterized by high regioselectivity favoring exo addition and by a high ratio of cyclization to reduction. Monocyclic, fused bicyclic, and spirocyclic lactones are formed in good to excellent yield. Use of allyltri-n-butyltin as a chain-transfer agent in the place of n-Bu3SnH affords the corresponding 3-butenyl lactones.

  DOI：

  10.1021/jo00043a030

文献信息

• New Strategies in Carbonylation Chemistry:  The Synthesis of δ-Lactones from Saturated Alcohols and CO
  作者：Shinji Tsunoi、Ilhyong Ryu、Tohru Okuda、Minoru Tanaka、Mitsuo Komatsu、Noboru Sonoda

  DOI：10.1021/ja9807892

  日期：1998.9.1

  δ-carbonylation of saturated alcohols which uses a 1,5-hydrogen-transfer reaction of alkoxyl radicals and subsequent carbonylation at the δ-carbon atoms as the key. The carbonylation reactions of five classes of saturated alcohols, namely, primary alcohols having primary δ-carbons, primary alcohols having secondary δ-carbons, primary alcohols having tertiary δ-carbons, secondary alcohols having primary δ-carbons

  本文描述了饱和醇的 δ-羰基化反应，它以烷氧基的 1,5-氢转移反应和随后在 δ-碳原子上的羰基化反应为关键。5类饱和醇的羰基化反应，即具有伯δ-碳的伯醇、具有仲δ-碳的伯醇、具有叔δ-碳的伯醇、具有伯δ-碳的仲醇、具有仲δ-碳的仲醇进行了碳，其中四乙酸铅（LTA）用作单电子氧化剂以产生烷氧基自由基。除了具有叔 δ-碳的伯醇外，这些饱和醇的羰基化以中等至良好的产率得到 δ-内酯。
• Novel photolactonisation from xanthenoic esters
  作者：Caroline Plessis、Sam Derrer

  DOI：10.1016/s0040-4039(01)01296-5

  日期：2001.9

  In the context of our work on photocleavable fragrance precursors, we have discovered a new photo-fragmentation of xanthenoic esters into xanthene- and formyl radicals. This homolytic cleavage has not been reported previously. Thus, unsaturated formyl radicals cyclise to lactones of various ring size. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Tutin, Journal of the Chemical Society, 1907, vol. 91, p. 272
  作者：Tutin

  DOI：——

  日期：——
• Podraza, Kenneth F., Journal of Heterocyclic Chemistry, 1987, vol. 24, p. 293 - 295
  作者：Podraza, Kenneth F.

  DOI：——

  日期：——
• PODRAZA, KENNETH F., J. HETEROCYCL. CHEM., 24,(1987) N 1, 293-295
  作者：PODRAZA, KENNETH F.

  DOI：——

  日期：——