(1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-11-hydroxy-7-(4-methoxybenzyloxy)-8,8,10,12-tetramethyl-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione | 479485-03-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-11-hydroxy-7-(4-methoxybenzyloxy)-8,8,10,12-tetramethyl-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione
• 英文别名: (1S,3S,7S,10R,11S,12S,16R)-11-hydroxy-7-[(4-methoxyphenyl)methoxy]-8,8,10,12-tetramethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
• CAS: 479485-03-5
• 化学式: C₃₄H₄₇NO₇S
• 分子量: 613.816
• InChiKey: WOOXAUXEPXOCLD-GWVIYHFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-11-hydroxy-7-(4-methoxybenzyloxy)-8,8,10,12-tetramethyl-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到西洛他唑
  参考文献：
  名称：

  Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands

  摘要：

  A [6]cavitand has been selectively derivatized on both the lower and upper rims. On the lower rim, two out of six potential sites were oxidized to produce a 1,4 substituted [6]cavitand bisketone, which was converted to a corresponding diol as well as a bisacetate [6]cavitand. The crystal structures of the bisketone and the diol were solved. On the upper rim, all six ArCH3 groups were selectively brominated to ArCH2Br groups to produce the hexabromomethyl [6]cavitand, which was converted to the corresponding hexabenzylthiol and hexabenzylthioacetate [6]cavitands. The conformational properties of all compounds are discussed.

  DOI：

  10.1002/1521-3765(20020816)8:16<3717::aid-chem3717>3.0.co;2-g
• 作为产物：
  描述：

  (Z)-(4S,7R,8S,9S,16S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5,5,7,9-tetramethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-oxacyclohexadec-13-ene-2,6-dione 在 二甲基二环氧乙烷 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 (1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-11-hydroxy-7-(4-methoxybenzyloxy)-8,8,10,12-tetramethyl-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione
  参考文献：
  名称：

  Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands

  摘要：

  A [6]cavitand has been selectively derivatized on both the lower and upper rims. On the lower rim, two out of six potential sites were oxidized to produce a 1,4 substituted [6]cavitand bisketone, which was converted to a corresponding diol as well as a bisacetate [6]cavitand. The crystal structures of the bisketone and the diol were solved. On the upper rim, all six ArCH3 groups were selectively brominated to ArCH2Br groups to produce the hexabromomethyl [6]cavitand, which was converted to the corresponding hexabenzylthiol and hexabenzylthioacetate [6]cavitands. The conformational properties of all compounds are discussed.

  DOI：

  10.1002/1521-3765(20020816)8:16<3717::aid-chem3717>3.0.co;2-g

文献信息

• Synthesis and Characterization of Upper and Lower Rim Functionalized [6]Cavitands
  作者：Christoph Naumann、Brian O. Patrick、John Sherman

  DOI：10.1002/1521-3765(20020816)8:16<3717::aid-chem3717>3.0.co;2-g

  日期：2002.8.16

  A [6]cavitand has been selectively derivatized on both the lower and upper rims. On the lower rim, two out of six potential sites were oxidized to produce a 1,4 substituted [6]cavitand bisketone, which was converted to a corresponding diol as well as a bisacetate [6]cavitand. The crystal structures of the bisketone and the diol were solved. On the upper rim, all six ArCH3 groups were selectively brominated to ArCH2Br groups to produce the hexabromomethyl [6]cavitand, which was converted to the corresponding hexabenzylthiol and hexabenzylthioacetate [6]cavitands. The conformational properties of all compounds are discussed.