1-[1-(pivaloyloxymethyl)ethenyl]cyclohexanecarboxylic acid | 468773-72-0

• 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: 1-[1-(pivaloyloxymethyl)ethenyl]cyclohexanecarboxylic acid
• 英文别名: 1-[3-(2,2-Dimethylpropanoyloxy)prop-1-en-2-yl]cyclohexane-1-carboxylic acid
• CAS: 468773-72-0
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: SGNFGEHSVRPDAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[1-(pivaloyloxymethyl)ethenyl]cyclohexanecarboxylic acid 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.0h， 以85%的产率得到3-spiro-1'-cyclohexane-4-methylenedihydro-2-(5H)-furanone
  参考文献：
  名称：

  Synthesis of spirocyclic β-methylene-γ-lactone utilizing hydroxymethylation of functionalized allylsilane

  摘要：

  A new spiro-beta-methylene-gamma-lactone annulation reaction is addressed for the synthesis of 4-methylene-2-oxaspiro[4.5]decan-1-one and its derivatives. 2-Cyclohexylidene-3-trimethylsilylprop-1-yl pivalate, obtained from cyclohexanone, was hydroxymethylated followed by desilylation to afford 2-[(1-hydroxymethyl)cyclohexyl]prop-2-en-1-yl pivalate and its -1-en-1-yl isomer. The former was oxidized to carboxylic acid followed by lactonization to the above compound. It was found that the stereochemistry of the hydroxymethylation reaction depends on the substituent on the cyclohexane ring. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00403-9
• 作为产物：
  描述：

  2-cyclohexylidene-3-trimethylsilylprop-1-yl pivalate 在 四丁基氟化铵 、 氯化二乙基铝 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-[1-(pivaloyloxymethyl)ethenyl]cyclohexanecarboxylic acid
  参考文献：
  名称：

  Synthesis of spirocyclic β-methylene-γ-lactone utilizing hydroxymethylation of functionalized allylsilane

  摘要：

  A new spiro-beta-methylene-gamma-lactone annulation reaction is addressed for the synthesis of 4-methylene-2-oxaspiro[4.5]decan-1-one and its derivatives. 2-Cyclohexylidene-3-trimethylsilylprop-1-yl pivalate, obtained from cyclohexanone, was hydroxymethylated followed by desilylation to afford 2-[(1-hydroxymethyl)cyclohexyl]prop-2-en-1-yl pivalate and its -1-en-1-yl isomer. The former was oxidized to carboxylic acid followed by lactonization to the above compound. It was found that the stereochemistry of the hydroxymethylation reaction depends on the substituent on the cyclohexane ring. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00403-9

文献信息

• Synthesis of spirocyclic β-methylene-γ-lactone utilizing hydroxymethylation of functionalized allylsilane
  作者：Chiaki Kuroda、Takahiro Kasahara、Kouki Akiyama、Takuma Amemiya、Takashi Kunishima、Yoshihiro Kimura

  DOI：10.1016/s0040-4020(02)00403-9

  日期：2002.5

  A new spiro-beta-methylene-gamma-lactone annulation reaction is addressed for the synthesis of 4-methylene-2-oxaspiro[4.5]decan-1-one and its derivatives. 2-Cyclohexylidene-3-trimethylsilylprop-1-yl pivalate, obtained from cyclohexanone, was hydroxymethylated followed by desilylation to afford 2-[(1-hydroxymethyl)cyclohexyl]prop-2-en-1-yl pivalate and its -1-en-1-yl isomer. The former was oxidized to carboxylic acid followed by lactonization to the above compound. It was found that the stereochemistry of the hydroxymethylation reaction depends on the substituent on the cyclohexane ring. (C) 2002 Elsevier Science Ltd. All rights reserved.