2-tert-butoxycarbonylamino-6-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-cyclopropyl]-4-ethoxythiocarbonylsulfanyl-6-oxo-hexanoic acid methyl ester | 823797-62-2

• 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: 2-tert-butoxycarbonylamino-6-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-cyclopropyl]-4-ethoxythiocarbonylsulfanyl-6-oxo-hexanoic acid methyl ester
• 英文别名: Methyl 6-[1-(1,3-dioxoisoindol-2-yl)cyclopropyl]-4-ethoxycarbothioylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohexanoate；methyl 6-[1-(1,3-dioxoisoindol-2-yl)cyclopropyl]-4-ethoxycarbothioylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohexanoate
• CAS: 823797-62-2
• 化学式: C₂₆H₃₂N₂O₈S₂
• 分子量: 564.681
• InChiKey: ILJQZGHFSBKIPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  186
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-tert-butoxycarbonylamino-6-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-cyclopropyl]-4-ethoxythiocarbonylsulfanyl-6-oxo-hexanoic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到(E)-2-tert-butoxycarbonylamino-6-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-cyclopropyl]-6-oxo-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  Generation and Intermolecular Capture of Cyclopropylacyl Radicals

  摘要：

  Cyclopropylacyl radicals derived from S-cyclopropylacyl xanthates (dithiocarbonates) undergo intermolecular additions to olefins without loss of CO or ring opening. In the presence of a phenyl ring on carbon C-1 of the cyclopropane ring, loss can be made to occur in the absence of an olefinic trap. The adducts from the cyclopropylacyl radical additions are easily converted into enones by base-induced beta-elimination of the xanthate group.

  DOI：

  10.1021/ol047892i
• 作为产物：
  描述：

  1-phthalimidocyclopropane-1-carbonyl chloride 在 DLP 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 2.25h， 生成 2-tert-butoxycarbonylamino-6-[1-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-cyclopropyl]-4-ethoxythiocarbonylsulfanyl-6-oxo-hexanoic acid methyl ester
  参考文献：
  名称：

  Generation and Intermolecular Capture of Cyclopropylacyl Radicals

  摘要：

  Cyclopropylacyl radicals derived from S-cyclopropylacyl xanthates (dithiocarbonates) undergo intermolecular additions to olefins without loss of CO or ring opening. In the presence of a phenyl ring on carbon C-1 of the cyclopropane ring, loss can be made to occur in the absence of an olefinic trap. The adducts from the cyclopropylacyl radical additions are easily converted into enones by base-induced beta-elimination of the xanthate group.

  DOI：

  10.1021/ol047892i

文献信息

• Generation and Intermolecular Capture of Cyclopropylacyl Radicals
  作者：Markus R. Heinrich、Samir Z. Zard

  DOI：10.1021/ol047892i

  日期：2004.12.1

  Cyclopropylacyl radicals derived from S-cyclopropylacyl xanthates (dithiocarbonates) undergo intermolecular additions to olefins without loss of CO or ring opening. In the presence of a phenyl ring on carbon C-1 of the cyclopropane ring, loss can be made to occur in the absence of an olefinic trap. The adducts from the cyclopropylacyl radical additions are easily converted into enones by base-induced beta-elimination of the xanthate group.