3-甲亚基环丁基乙酸酯 | 18218-27-4

• 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
• 中文名称: 3-甲亚基环丁基乙酸酯
• 英文名称: 3-acetoxy-1-methylenecyclobutane
• 英文别名: 3-Methylenecyclobutylacetate；(3-methylidenecyclobutyl) acetate
• CAS: 18218-27-4
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: GECKEGSNKRNFFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  3-acetoxy-3-chloromercurio-1-methylenecyclobutane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 3-甲亚基环丁基乙酸酯
  参考文献：
  名称：

  Zefirov, N. S.; Surmina, L. S.; Sadovaya, N. K., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 11, p. 2002 - 2014

  摘要：

  DOI：

文献信息

• Stereochemistry of the Deamination of Spiropentylamine
  作者：Kenneth B. Wiberg、Carmen Österle

  DOI：10.1021/jo990654u

  日期：1999.10.1

  The stereochemistry of the deamination of (-)-spiropentylamine in acetic acid has been studied, and it was found that one of the major products, (-)-spiropentyl acetate, was formed with essentially complete inversion of configuration. This suggests that it is formed via an S(N)2 displacement on the spiropentyldiazonium ion. The stereochemistry was established by the conversion of(-)-spiropentanecarboxylic acid to (-)-spiropentylamine via a Curtius rearrangement that proceeds with retention of configuration. The (-) acid also was converted to spiropentyl methyl ketone with methyllithium and then to (+)-spiropentyl acetate via the Baeyer-Villiger reaction that also results in retention of configuration. The deamination of N-nitroso-N-spiropentyl urea was studied in methanol, and spiropentyl methyl ether was a major product. Similarly, the reaction in water led to spiropentanol. The latter reactions also lead to 2-methoxymethyl- or 2-hydroxymethyl-1,3-butadiene, respectively, corresponding to the alternative mode of reaction via a cyclopropyl cation-allyl cation rearrangement.
• [1.1.1]Propellane
  作者：Kenneth B. Wiberg、Frederick H. Walker

  DOI：10.1021/ja00383a046

  日期：1982.9
• Vibrational spectrum, structure, and energy of [1.1.1]propellane
  作者：Kenneth B. Wiberg、William P. Dailey、Frederick H. Walker、Sherman T. Waddell、Louis S. Crocker、Marshall Newton

  DOI：10.1021/ja00311a003

  日期：1985.12
• ZEFIROV, N. S.;SURMINA, L. S.;SADOVAYA, N. K.;BLOXIN, A. V.;TYUREXODZHAEV+, ZH. ORGAN. XIMII, 26,(1990) N1, S. 2317-2333
  作者：ZEFIROV, N. S.、SURMINA, L. S.、SADOVAYA, N. K.、BLOXIN, A. V.、TYUREXODZHAEV+

  DOI：——

  日期：——
• US5405550A
  申请人：——

  公开号：US5405550A

  公开（公告）日：1995-04-11