(2R,3S)-1-iodooctane-2,3-diol | 127280-35-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R,3S)-1-iodooctane-2,3-diol
• CAS: 127280-35-7
• 化学式: C₈H₁₇IO₂
• 分子量: 272.126
• InChiKey: CSKAZRPQZFXCJF-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-iodooctane-2,3-diol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.0h， 生成 (2S,3S)-2,3-octanediol
  参考文献：
  名称：

  Diols obtained via chemo and regioselective ring opening of epoxy alcohols: a straightforward synthesis of 2S,3S-Octandiol

  摘要：

  Epoxy alcohols are regio and chemoselectively opened to the corresponding iodohydrins and then reduced in situ to diols; the application of the described procedure leads to a short asymmetric synthesis of a well known pheromone. Also homoallylic (E and Z) epoxy alcohols and its benzylated derivatives shows high preference for regioselective opening affording the corresponding 1,3 diol.

  DOI：

  10.1016/s0040-4020(01)92240-9
• 作为产物：
  描述：

  1-辛烯-3-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 甲酸 、 D(+)-DIPT 、 sodium 、 三苯基膦 、 magnesium iodide 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.17h， 生成 (2R,3S)-1-iodooctane-2,3-diol
  参考文献：
  名称：

  Diols obtained via chemo and regioselective ring opening of epoxy alcohols: a straightforward synthesis of 2S,3S-Octandiol

  摘要：

  Epoxy alcohols are regio and chemoselectively opened to the corresponding iodohydrins and then reduced in situ to diols; the application of the described procedure leads to a short asymmetric synthesis of a well known pheromone. Also homoallylic (E and Z) epoxy alcohols and its benzylated derivatives shows high preference for regioselective opening affording the corresponding 1,3 diol.

  DOI：

  10.1016/s0040-4020(01)92240-9

文献信息

• C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide
  作者：Carlo Bonini、Chiara Federici、Leucio Rossi、Giuliana Righi

  DOI：10.1021/jo00120a025

  日期：1995.7

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.
• Mild and stereocontrolled synthesis of iodo- and bromohydrins by halogen-tetrakis(isopropoxy)titanium opening of epoxy alcohols
  作者：Eleuterio Alvarez、Maria Teresa Nunez、Victor S. Martin

  DOI：10.1021/jo00298a002

  日期：1990.5
• ALVAREZ, ELEUTERIO;NUNEZ, MARIA TERESA;MARTIN, VICTOR S., J. ORG. CHEM., 55,(1990) N1, C. 3429-3431
  作者：ALVAREZ, ELEUTERIO、NUNEZ, MARIA TERESA、MARTIN, VICTOR S.

  DOI：——

  日期：——