4-(2-iodo-1-oxopropyl)-(7R)-10,10-dimethyl-5-thia-4-azatricyclo<5.2.1.0>decane-5,5-dioxide | 128869-13-6

• 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: 4-(2-iodo-1-oxopropyl)-(7R)-10,10-dimethyl-5-thia-4-azatricyclo<5.2.1.0>decane-5,5-dioxide
• 英文别名: 1-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-2-iodopropan-1-one
• CAS: 128869-13-6
• 化学式: C₁₃H₂₀INO₃S
• 分子量: 397.277
• InChiKey: ZPOXGXSBNFSNLR-CRNWHOSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(2-iodo-1-oxopropyl)-(7R)-10,10-dimethyl-5-thia-4-azatricyclo<5.2.1.0>decane-5,5-dioxide 在 三乙基硼 、 氧气 、 甲醇 、 二甲基硫 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 5.25h， 以98%的产率得到4-(2-iodopropanoyl)-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione
  参考文献：
  名称：

  Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives

  摘要：

  [GRAPHICS]Treatment of alpha-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding a-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the alpha-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently converted to alcohols, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.

  DOI：

  10.1021/ol990971n
• 作为产物：
  描述：

  N-丙酰基-(2R)-樟烷-10,2-磺内酰胺 在 lithium diisopropyl amide 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以79%的产率得到4-(2-iodo-1-oxopropyl)-(7R)-10,10-dimethyl-5-thia-4-azatricyclo<5.2.1.0>decane-5,5-dioxide
  参考文献：
  名称：

  Efficient Radical Oxygenation of α-Iodocarboxylic Acid Derivatives

  摘要：

  [GRAPHICS]Treatment of alpha-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding a-hydroxy acid derivatives. This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of triethylborane and oxygen, with the alpha-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimination product is observed, tertiary iodides are efficiently converted to alcohols, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.

  DOI：

  10.1021/ol990971n

文献信息

• Asymmetric radical addition, cyclization, and annulation reactions with Oppolzer's camphor sultam
  作者：Dennis P. Curran、Wang Shen、Jiancun Zhang、Timothy A. Heffner

  DOI：10.1021/ja00174a059

  日期：1990.8
• Curran, Dennis P.; Shen, Wang; Zhang, Jiancun, Heterocycles, 1994, vol. 37, # 3, p. 1773 - 1788
  作者：Curran, Dennis P.、Shen, Wang、Zhang, Jiancun、Gieb, Steven J.、Lin, Chien-Hsing

  DOI：——

  日期：——
• CURRAN, DENNIS P.;SHEN, WANG;ZHANG, JIANCUN;HEFFNER, TIMOTHY A., J. AMER. CHEM. SOC., 112,(1990) N8, C. 6738-6740
  作者：CURRAN, DENNIS P.、SHEN, WANG、ZHANG, JIANCUN、HEFFNER, TIMOTHY A.

  DOI：——

  日期：——
• Curran Dennis P., Shen Wang, Zhang Jiancun, Gieb Steven J., Lin Chien-Hsi+, Heterocycles, 37 (1994) N 3, S 1773-1788
  作者：Curran Dennis P., Shen Wang, Zhang Jiancun, Gieb Steven J., Lin Chien-Hsi+

  DOI：——

  日期：——