[(1R,2S)-2-[(1R,2R)-2-[(1S,2R)-2-(hydroxymethyl)cyclopropyl]cyclopropyl]cyclopropyl]methanol | 194595-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1R,2S)-2-[(1R,2R)-2-[(1S,2R)-2-(hydroxymethyl)cyclopropyl]cyclopropyl]cyclopropyl]methanol
• CAS: 194595-38-5
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: JDGWBFBOYFBTLQ-OVFHJWECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  3.0
• 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：

  [(1R,2S)-2-[(1R,2R)-2-[(1S,2R)-2-(hydroxymethyl)cyclopropyl]cyclopropyl]cyclopropyl]methanol 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of the Quinquecyclopropane-Containing Cholesteryl Ester Transfer Protein Inhibitor U-106305

  摘要：

  DOI：

  10.1021/ja961399n
• 作为产物：
  描述：

  (±)-(1S,2S)-cyclopropane-1,2-dicarbaldehyde 在 乙二醇二甲醚 、 (2S,3S)-N,N,N',N'-tetramethylsuccindiamide-2,3-dioxa-n-butylborolane 、 4 A molecular sieve 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 [(1R,2S)-2-[(1R,2R)-2-[(1S,2R)-2-(hydroxymethyl)cyclopropyl]cyclopropyl]cyclopropyl]methanol
  参考文献：
  名称：

  Total Synthesis and Stereochemical Assignment of the Quinquecyclopropane-Containing Cholesteryl Ester Transfer Protein Inhibitor U-106305

  摘要：

  DOI：

  10.1021/ja961399n

文献信息

• Iterative Cyclopropanation:  A Concise Strategy for the Total Synthesis of the Hexacyclopropane Cholesteryl Ester Transfer Protein Inhibitor U-106305
  作者：Anthony G. M. Barrett、Dieter Hamprecht、Andrew J. P. White、David J. Williams

  DOI：10.1021/ja9708326

  日期：1997.9.1

  The first enantioselective total synthesis of the hexacyclopropane natural product U-106305, which is produced by Streptomyces sp. UC 11136, is described in full detail. Considerations on the biosynthesis of U-106305 and its close resemblance to the pentacyclopropane bacterial metabolite FR-900848 (10) led to the proposal that its previously unknown stereostructure should be represented as 11. The

  第一个对映选择性全合成六环丙烷天然产物 U-106305，由 Streptomyces sp. 产生。UC 11136 进行了详细描述。考虑到 U-106305 的生物合成及其与五环丙烷细菌代谢物 FR-900848 (10) 的相似性，建议其先前未知的立体结构应表示为 11。11 的中央 C2 对称五环丙烷单元由以有效的双向方法重复使用三步环丙烷“同源”序列。去对称的五环丙烷 23 被转化为二烯醇 13，二烯醇 13 被立体和区域选择性地单环丙烷化以提供六环丙烷 25。通过转化为硫醚 29 和脱硫来实现脱氧。
• Studies on Mercury(II)-Mediated Opening of Bi- and Tercyclopropane Arrays
  作者：Anthony G. M. Barrett、William Tam

  DOI：10.1021/jo970464o

  日期：1997.7.1

  The first examples of the mercury(II)-mediated ring opening of bicyclopropane and tercyclopropane arrays have been investigated. The presence of an adjacent cyclopropyl group dramatically increased the rate of the mercury-mediated opening of the first cyclopropane in a cyclopropane array. In contrast to the mercury-mediated ring opening of monocyclopropanes which usually undergo a concerted ring-opening mechanism, electrophilic openings of cyclopropane arrays occurred through a stabilized, free carbocation. Excellent regio- and stereoselectivities were observed in the mercury-mediated intramolecular openings of the second cyclopropanes in the cyclopropane arrays, giving rise to the formation of enantiomerically pure, highly substituted tetrahydrofurans.