Spiroheptane-2,2'-cyclopentane>-1,3-dione | 62248-58-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Spiroheptane-2,2'-cyclopentane>-1,3-dione
• 英文别名: 5,8-methanospiro<4.5>decane-1,4-dione；Spiro[bicyclo[2.2.1]heptane-2,1'-cyclopentane]-2',5'-dione；spiro[bicyclo[2.2.1]heptane-2,2'-cyclopentane]-1',3'-dione
• CAS: 62248-58-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: CIJVKXPUCZGQPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-二甲氧基降冰片烷 在 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.67h， 生成 Spiroheptane-2,2'-cyclopentane>-1,3-dione
  参考文献：
  名称：

  RING EXPANSION AND CLEAVAGE OF SUCCINOIN DERIVATIVES: SPIRO[4.5]DECANE-1,4-DIONE AND ETHYL 4-CYCLOHEXYL-4-OXOBUTANOATE

  摘要：

  DOI：

  10.15227/orgsyn.065.0017

文献信息

• Lewis Acid Catalyzed Geminal Acylation Reaction of Ketones with 1,2-Bis[(trimethylsilyl)oxy]cyclobutene: Direct Formation of 2,2-Disubstituted 1,3-Cyclopentanediones
  作者：Tracy J. Jenkins、D. Jean Burnell

  DOI：10.1021/jo00085a041

  日期：1994.3

  Ketones reacted with 1,2-bis((trimethylsilyl)oxy)cyclobutene (1) under catalysis by boron trifluoride etherate to yield 2,2-disubstituted 1,3-cyclopentanedione products via silylated cyclobutanone intermediates in a two-step, one-pot process. In many instances addition of a small amount of water to the reaction medium after completion of the first step assisted the subsequent rearrangement to the product, such that reversion of the intermediate to the starting ketone became an insignificant process. Yields were best with cyclohexanones (>90%), but steric hindrance and conjugated double bonds reduced yields considerably.
• Ring expansion and cleavage of succinoin derivatives. Geminal acylation, reductive succinoylation, and stereoselective spiro annelation methods
  作者：Junichi Shimada、Koichi Hashimoto、Byeang Hyean Kim、Eiichi Nakamura、Isao Kuwajima

  DOI：10.1021/ja00318a035

  日期：1984.3
• Burnell, D. Jean; Wu, Yong-Jin, Canadian Journal of Chemistry, 1990, vol. 68, # 6, p. 804 - 811
  作者：Burnell, D. Jean、Wu, Yong-Jin

  DOI：——

  日期：——
• NAKAMURA, EIICHI;KUWAJIMA, ISAO, ORG. SYNTH., NEW YORK ETC.,(1987) C. 17-25
  作者：NAKAMURA, EIICHI、KUWAJIMA, ISAO

  DOI：——

  日期：——
• SHIMADA, J. -ICHI;HASHIMOTO, KOICHI;KIM, BYEANG, HYEAN;NAKAMURA, EIICHI;K+, J. AMER. CHEM. SOC., 1984, 106, N 6, 1759-1773
  作者：SHIMADA, J. -ICHI、HASHIMOTO, KOICHI、KIM, BYEANG, HYEAN、NAKAMURA, EIICHI、K+

  DOI：——

  日期：——