(1S,8S,3Z)-1-[(1E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)vinyl]-8-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(tert-butyldimethylsilyloxy)non-3-ene | 479484-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1S,8S,3Z)-1-[(1E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)vinyl]-8-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(tert-butyldimethylsilyloxy)non-3-ene
• 英文别名: tert-butyl-[(1E,3S,5Z,10S)-10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)undeca-1,5-dien-3-yl]oxy-dimethylsilane
• CAS: 479484-98-5
• 化学式: C₂₇H₄₇NO₃SSi
• 分子量: 493.827
• InChiKey: ZCJMGRMJCFVWRA-SDONHTGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.15
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,8S,3Z)-1-[(1E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)vinyl]-8-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(tert-butyldimethylsilyloxy)non-3-ene 在 CuCl₂*H₂O 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以79.6%的产率得到(7Z,11E)-(2R,3S,10S)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-12-(2-methyl-thiazol-4-yl)-dodeca-7,11-diene-1,2-diol
  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：

  (4R)-4-[(2S)-5-bromopentan-2-yl]-2,2-dimethyl-1,3-dioxolane 在 Lindlar's catalyst 咪唑 、 正丁基锂 、 草酰氯 、 potassium tert-butylate 、 氨 、 氢气 、 sodium 、 4-甲基苯磺酸吡啶 、 lithium 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.92h， 生成 (1S,8S,3Z)-1-[(1E)-1-methyl-2-(2-methyl-1,3-thiazol-4-yl)vinyl]-8-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(tert-butyldimethylsilyloxy)non-3-ene
  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.