(Z)-(S)-10-[(E)-1-Methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one | 252265-31-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奥昔康唑
• 英文名称: (Z)-(S)-10-[(E)-1-Methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one
• 英文别名: (2S,4Z)-2-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-2,3,6,7,8,9-hexahydrooxecin-10-one
• CAS: 252265-31-9
• 化学式: C₁₆H₂₁NO₂S
• 分子量: 291.414
• InChiKey: PXRHDFPSNJGIEI-SZVLQLAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-(S)-10-[(E)-1-Methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one 在 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 、 sodium hexamethyldisilazane 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3S,10S,7Z,11E)-(tert-butyldimethylsilyloxy)-3,11-dimethyl-12-(2-methyl-1,3-thiazol-4-yl)dodeca-7,11-diene-1,2-diol
  参考文献：
  名称：

  Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylation

  摘要：

  An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01659-7
• 作为产物：
  描述：

  6-庚烯酸 在 Grubbs catalyst first generation 、 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (Z)-(S)-10-[(E)-1-Methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one
  参考文献：
  名称：

  Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylation

  摘要：

  An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01659-7

文献信息

• Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylation
  作者：Monika Quitschalle、Markus Kalesse

  DOI：10.1016/s0040-4039(99)01659-7

  日期：1999.10

  An improved synthesis of the northern hemisphere of epothilone A is described. This approach utilizes the Sharpless asymmetric dihydroxylation of 5-hexen-2-one (allyl acetone) to generate the precursor for the Wittig reaction and the subsequent ring closing metathesis reaction (RCM). This strategy allows to generate precursor 13 as both enantiomers from ready available starting material in a very efficient manner. (C) 1999 Elsevier Science Ltd. All rights reserved.