(1S,2R,4R,5R)-4-iodo-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,2R,4R,5R)-4-iodo-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid
• 化学式: C₈H₉IO₄
• 分子量: 296.062
• InChiKey: KCKXBXSJLWDSNV-JGWLITMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R,5R)-4-iodo-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid 在 咪唑 、 sodium tetrahydroborate 、 氯甲酸乙酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.0h， 生成 (1R,2R,5R)-2-<(tert-Butyldimethylsilyloxy)methyl>-6-oxabicyclo<3.2.1>oct-3-en-7-one
  参考文献：
  名称：

  通过化学酶促方法对环己烯酮衍生物的对映选择性合成：立体和区域选择性途径，生成紧密蛋白（ML 236B）和美维林的潜在中间体。

  摘要：

  作为手性单酯2的合成应用，研究了通过猪肝酯酶（PLE）催化水解相应的内消旋二酯1制备的手性单酯2，将2转化为各种环己烯酮衍生物。本文描述了异构体环己烯酮6和7的制备方法，这些化合物是在立体和区域选择性控制下合成抗高胆固醇紧缩蛋白（ML 236B）和美维诺林的潜在中间体。

  DOI：

  10.1248/cpb.38.1479
• 作为产物：
  描述：

  cis-1,2,3,6-tetrahydrophthalic anhydride 在 碘 、 碳酸氢钠 、 potassium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 26.0h， 以70%的产率得到(1S,2R,4R,5R)-4-iodo-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylic acid
  参考文献：
  名称：

  Conformational Control in Activation of an Enediyne

  摘要：

  In the bicyclo[7.3.1]tridec-4-ene-2,6-diyne framework characteristic of calicheamicin, DFT calculations predict that the chair conformer should be much more reactive toward cycloaromatization compared to the boat form. A functionalized derivative of this framework with an added two-atom bridge to enforce the boat conformation was synthesized and shown to be stable at 23 degrees C. Cleavage of the bridge releases the conformational lock and cycloaromatization proceeds with t1/2 42.5 min/23 degrees C, presumably through the chair conformation. This confirms the prediction based on computation and points to a new principle for triggering the enediyne toxins.

  DOI：

  10.1021/ja036763e

文献信息

• New Radical Allylation Reaction of Iodides
  作者：Frédéric Le Guyader、Béatrice Quiclet-Sire、Stéphanie Seguin、Samir Z. Zard

  DOI：10.1021/ja9708878

  日期：1997.8.1
• KOBAYASHI, SUSUMU;EGUCHI, YOSHIHITO;SHIMADA, MITSUYUKI;OHNO, MASAJI, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1479-1484
  作者：KOBAYASHI, SUSUMU、EGUCHI, YOSHIHITO、SHIMADA, MITSUYUKI、OHNO, MASAJI

  DOI：——

  日期：——
• Conformational Control in Activation of an Enediyne
  作者：M. F. Semmelhack、Lingyun Wu、Robert A. Pascal、Douglas M. Ho

  DOI：10.1021/ja036763e

  日期：2003.9.1

  In the bicyclo[7.3.1]tridec-4-ene-2,6-diyne framework characteristic of calicheamicin, DFT calculations predict that the chair conformer should be much more reactive toward cycloaromatization compared to the boat form. A functionalized derivative of this framework with an added two-atom bridge to enforce the boat conformation was synthesized and shown to be stable at 23 degrees C. Cleavage of the bridge releases the conformational lock and cycloaromatization proceeds with t1/2 42.5 min/23 degrees C, presumably through the chair conformation. This confirms the prediction based on computation and points to a new principle for triggering the enediyne toxins.
• Enantioselective synthesis of cyclohexenone derivatives by a chemicoenzymatic approach: Stereo- and regioselective route to potential intermediates of compactin (ML 236B) and mevinolin.
  作者：Susumu KOBAYASHI、Yoshihito EGUCHI、Mitsuyuki SHIMADA、Masaji OHNO

  DOI：10.1248/cpb.38.1479

  日期：——

  of 2 into various cyclohexenone derivatives was examined. This paper describes the preparation of the isomeric cyclohexenones 6 and 7, potential intermediates for the synthesis of anti-hypercholesmic compactin (ML 236B) and mevinolin, under stereo- and regioselective control.

  作为手性单酯2的合成应用，研究了通过猪肝酯酶（PLE）催化水解相应的内消旋二酯1制备的手性单酯2，将2转化为各种环己烯酮衍生物。本文描述了异构体环己烯酮6和7的制备方法，这些化合物是在立体和区域选择性控制下合成抗高胆固醇紧缩蛋白（ML 236B）和美维诺林的潜在中间体。