(+/-)-2-(3-Iodopropanyl)succinimidespiro-3'-cyclopentane | 143582-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (+/-)-2-(3-Iodopropanyl)succinimidespiro-3'-cyclopentane
• 英文别名: 4-(3-Iodopropyl)-2-azaspiro[4.4]nonane-1,3-dione
• CAS: 143582-41-6
• 化学式: C₁₁H₁₆INO₂
• 分子量: 321.158
• InChiKey: IYPATYFTOACOBG-UHFFFAOYSA-N

物化性质

• 沸点：
  443.7±18.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(3-Iodopropanyl)succinimidespiro-3'-cyclopentane 在 ruthenium trichloride 、 高碘酸 作用下， 以 四氯化碳 、 乙醚 、 水 、 乙腈 为溶剂， 反应 7.5h， 生成 3-(1,3-Dioxo-2-aza-spiro[4.4]non-4-yl)-propionic acid methyl ester
  参考文献：
  名称：

  A Mild and Efficient Oxidation of Primary Alkyl Iodides to Carboxylic Acids

  摘要：

  DOI：

  10.1055/s-1992-26190
• 作为产物：
  描述：

  2-环亚戊基环戊酮 在 碘苯二乙酸 、 水 、 碘 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 55.0h， 生成 (+/-)-2-(3-Iodopropanyl)succinimidespiro-3'-cyclopentane
  参考文献：
  名称：

  Syntheses of Substituted Succinimides by Radical .beta.-Fragmentation of Bicyclic Carbinol Amides. A New Expeditious Synthesis of 2-[2-(Methoxycarbonyl)ethyl]-3-[(methoxycarbonyl)methyl]- 3-methylsuccinimide, the Ring-B Imide of Vitamin B12

  摘要：

  A mild and efficient synthesis of substituted succinimides by radical beta-fragmentation of carbinol amides is described. The carbinol amides studied were generated by treatment of the corresponding alpha,beta-unsaturated ketones with hydrogen cyanide and subsequent hydrolysis of the cyanide intermediates. Photolysis with visible light in the presence of (diacetoxyiodo)benzene (DIB) and iodine of azabicyclic carbinol amides of the types 1-hydroxy-2-azabicyclo[3.3.0] octan-3-one (e.g., 4, 6, and 7) and 1-hydroxy-2-azabicyclo[3.2.1]octan-3-one (e.g., 16, 17, and 21) led to the substituted succinimides in good yields. A novel and operationally simple synthesis of the ring-B imide 28 is described, employing this P-fragmentation reaction on the carbinol amide 7 as the key step. The transformation of the resulting succinimide 11 into the target 28 was accomplished in one step by oxidation of the primary iodide and the phenyl group with RUO(4).

  DOI：

  10.1021/jo00089a021

文献信息

• A selenurane derivative promotes β-fragmentation of carbinolamides leading to cyclic imides
  作者：Rosa L. Dorta、Cosme G. Francisco、Ernesto Suárez

  DOI：10.1016/s0040-4039(00)79971-0

  日期：1994.2

  The alkoxy radical intermediates generated by reaction of carbinolamides with diphenylselenium hydroxyacetate (1) in the presence of iodine and under irradiation with visible light undergo beta-fragmentation to afford 3,4-substituted cyclic imides in good yields.
• Dorta Rosa L., Francisco Cosme G., Suarez Ernesto, Tetrahedron Lett, 35 (1994) N 7, S 1083-1087
  作者：Dorta Rosa L., Francisco Cosme G., Suarez Ernesto

  DOI：——

  日期：——
• A Mild and Efficient Oxidation of Primary Alkyl Iodides to Carboxylic Acids
  作者：Rosendo Hernández、Daniel Melián、Ernesto Suárez

  DOI：10.1055/s-1992-26190

  日期：——
• Syntheses of Substituted Succinimides by Radical .beta.-Fragmentation of Bicyclic Carbinol Amides. A New Expeditious Synthesis of 2-[2-(Methoxycarbonyl)ethyl]-3-[(methoxycarbonyl)methyl]- 3-methylsuccinimide, the Ring-B Imide of Vitamin B12
  作者：Rosendo Hernandez、Ernesto Suarez、Daniel Melian

  DOI：10.1021/jo00089a021

  日期：1994.5

  A mild and efficient synthesis of substituted succinimides by radical beta-fragmentation of carbinol amides is described. The carbinol amides studied were generated by treatment of the corresponding alpha,beta-unsaturated ketones with hydrogen cyanide and subsequent hydrolysis of the cyanide intermediates. Photolysis with visible light in the presence of (diacetoxyiodo)benzene (DIB) and iodine of azabicyclic carbinol amides of the types 1-hydroxy-2-azabicyclo[3.3.0] octan-3-one (e.g., 4, 6, and 7) and 1-hydroxy-2-azabicyclo[3.2.1]octan-3-one (e.g., 16, 17, and 21) led to the substituted succinimides in good yields. A novel and operationally simple synthesis of the ring-B imide 28 is described, employing this P-fragmentation reaction on the carbinol amide 7 as the key step. The transformation of the resulting succinimide 11 into the target 28 was accomplished in one step by oxidation of the primary iodide and the phenyl group with RUO(4).