6-[tert-butyl(dimethyl)silyl]oxy-6-[(Z)-7-(oxan-2-yloxy)hept-3-en-1,5-diynyl]cyclohex-2-en-1-one | 150637-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-[tert-butyl(dimethyl)silyl]oxy-6-[(Z)-7-(oxan-2-yloxy)hept-3-en-1,5-diynyl]cyclohex-2-en-1-one
• CAS: 150637-64-2
• 化学式: C₂₄H₃₄O₄Si
• 分子量: 414.617
• InChiKey: PRGOLMDUXFGQMU-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-[tert-butyl(dimethyl)silyl]oxy-6-[(Z)-7-(oxan-2-yloxy)hept-3-en-1,5-diynyl]cyclohex-2-en-1-one 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 Bicyclo[7.3.1]tridec-4-ene-2,6-diyn-13-one,1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-hydroxy-10-(phenylthio)-
  参考文献：
  名称：

  Conjugate addition-aldol approach to the simple bicyclic-diynene core structure found in the esperamicins and calicheamicins

  摘要：

  The stable 12-beta-hydroxybicyclo[7.1.0] diynene core 15 has been prepared stereospecifically. The key step consists of conjugate addition of dimethylaluminum benzenethiolate to enone aldehyde 12 followed by an in situ titanium isopropoxide assisted aldol cyclization to produce alcohol 13 as a single isomer.

  DOI：

  10.1016/s0040-4039(00)91637-x
• 作为产物：
  描述：

  (Z)-1-choro-5-<(2-tetrahydropyranyl)oxy>-1-penten-3-yne 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 6-[tert-butyl(dimethyl)silyl]oxy-6-[(Z)-7-(oxan-2-yloxy)hept-3-en-1,5-diynyl]cyclohex-2-en-1-one
  参考文献：
  名称：

  Conjugate addition-aldol approach to the simple bicyclic-diynene core structure found in the esperamicins and calicheamicins

  摘要：

  The stable 12-beta-hydroxybicyclo[7.1.0] diynene core 15 has been prepared stereospecifically. The key step consists of conjugate addition of dimethylaluminum benzenethiolate to enone aldehyde 12 followed by an in situ titanium isopropoxide assisted aldol cyclization to produce alcohol 13 as a single isomer.

  DOI：

  10.1016/s0040-4039(00)91637-x

文献信息

• A general strategy using η2co2(co)6 acetylene complexes for the synthesis of the enediyne antitumor agents esperamicin, calicheamicin, dy
  作者：Philip Magnus

  DOI：10.1016/s0040-4020(01)80626-8

  日期：1994.1

  A review of the use of η2Co2(CO)6-acetylene complexes as stable intermediates for the construction of the core structures of the antitumo

  使用的审查η 2共2（CO）6个-acetylene络合物作为稳定的中间体，用于antitumo的核心结构的构造中
• Synthesis of a Protected (±)-Calicheamicinone Derivative by Sequential Introduction of Functionality into the Bicyclo[7.3.1]enediyne Core Structure
  作者：Philip Magnus、Gregory F. Miknis、Neil J. Press、Didier Grandjean、G. Mark Taylor、John Harling

  DOI：10.1021/ja970743t

  日期：1997.7.1

  The core bicyclo[7.3.0]enediyne 3 has been synthesized from the protected cyclohexane-1,2-dione 6 and enediyne component 9. Conversion of 20 into more highly functionalized enediynes was accomplished by oxidation and amination to give 27. Protection of 27, and conversion into 31, gave on treatment with (MeO)2P(O)CH2CO2Me the lactone 32, which was transformed into the trisulfide 39. All attempts to

  核心双环 [7.3.0] 烯二炔 3 由受保护的环己烷-1,2-二酮 6 和烯二炔组分 9 合成。通过氧化和胺化将 20 转化为更高官能化的烯二炔，得到 27。 27 的保护，并转化为 31，在用 (MeO)2P(O)CH2CO2Me 处理后得到内酯 32，后者转化为三硫化物 39。所有尝试使用其他工作人员成功应用于类似底物的条件对 39 进行脱保护，仅导致环状硫化物 42 和 43。