(S)-5-iodopentane-1,2-diol | 879223-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-5-iodopentane-1,2-diol
• CAS: 879223-49-1
• 化学式: C₅H₁₁IO₂
• 分子量: 230.046
• InChiKey: UZEWADVWFPPTPP-YFKPBYRVSA-N

物化性质

• 沸点：
  286.8±30.0 °C(Predicted)
• 密度：
  1.836±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  8.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-5-iodopentane-1,2-diol 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(S)-4,5-bis((tert-butyldimethylsilyl)oxy)-1-iodo-pentane
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115
• 作为产物：
  描述：

  (S)-4-(3-iodopropyl)-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到(S)-5-iodopentane-1,2-diol
  参考文献：
  名称：

  Total synthesis of diastereomeric marine butenolides possessing a syn-aldol subunit at C10 and C11 and the related C11-ketone

  摘要：

  Two diastereomeric marine butenolides. (4S,10R,11R)- and (4S,10S,11S)-4,11-dihydroxy-10-methyldodec2-en-1,4-olide, possessing a syn-aldol subunit at C10 and C11 have been efficiently synthesized by using a three-module coupling strategy. The enantiomeric syn-aldol modules prepared by the syn-selective aldol reaction of the norephedrine-derived chiral propionates were coupled with the chiral C3-C7 module via 1,3-dithiane bisalkylation. The butenolide ring was then installed via a high-yielding ring-closing metathesis (RCM) reaction. Oxidation of the diastereomeric C11-alcohols furnished the corresponding C11-ketones, which are produced by the same marine microorganism. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.115