(2Z,4R,5R,8R,9R,10S,12E)-1-tert-butyldimethylsilyloxy-4-ethyl-5-hydroxy-9-methoxy-8,10-dimethyl-2,12-tetradecadien-7-one | 216174-63-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2Z,4R,5R,8R,9R,10S,12E)-1-tert-butyldimethylsilyloxy-4-ethyl-5-hydroxy-9-methoxy-8,10-dimethyl-2,12-tetradecadien-7-one
• 英文别名: (2Z,4R,5R,8R,9R,10S,12E)-1-[tert-butyl(dimethyl)silyl]oxy-4-ethyl-5-hydroxy-9-methoxy-8,10-dimethyltetradeca-2,12-dien-7-one
• CAS: 216174-63-9
• 化学式: C₂₅H₄₈O₄Si
• 分子量: 440.739
• InChiKey: AETOZHXGNMHKHU-DTUCOOSKSA-N

物化性质

• 沸点：
  496.7±45.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  30.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2Z,4R,5R,8R,9R,10S,12E)-1-tert-butyldimethylsilyloxy-4-ethyl-5-hydroxy-9-methoxy-8,10-dimethyl-2,12-tetradecadien-7-one 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 lithium iodide 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 6.0h， 生成 5-乙基-5,6-二氢-6-[(2R,3S,4R,5S,7E)-2-羟基-4-甲氧基-3,5-二甲基-7-壬烯-1-基]-,(5R,6R)-2H-吡喃-2-酮
  参考文献：
  名称：

  An efficient synthesis of pironetins employing a useful chiral building block,(1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one

  摘要：

  A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00556-6
• 作为产物：
  描述：

  (2S,3R,4Z)-6-tert-butyldimethylsilyloxy-3-ethyl-1-p-toluenesulfonyloxy-4-hexene-2-ol 在 2,6-二甲基吡啶 、 正丁基锂 、 mercury(II) perchlorate 、 碳酸氢钠 、 potassium carbonate 、 calcium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (2Z,4R,5R,8R,9R,10S,12E)-1-tert-butyldimethylsilyloxy-4-ethyl-5-hydroxy-9-methoxy-8,10-dimethyl-2,12-tetradecadien-7-one
  参考文献：
  名称：

  An efficient synthesis of pironetins employing a useful chiral building block,(1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one

  摘要：

  A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00556-6

文献信息

• Total synthesis of (−)-pironetin
  作者：Hiroyuki Watanabe、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/s0040-4039(98)01860-7

  日期：1998.11

  The convergent total synthesis of (-)-pironetin using a chiral building block, (1S,5S,6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described Both the dithiane 4 and the epoxide 2 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 15, which was converted to pironetin 1 in a few steps. (C) 1998 Elsevier Science Ltd. All rights reserved.