tert-butyl-dimethyl-[(1'R,2'R,6'S,8'R)-6'-methylspiro[1,3-dioxolane-2,5'-9,12-dioxatricyclo[6.3.1.01,6]dodec-10-ene]-2'-yl]oxysilane | 935528-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-dimethyl-[(1'R,2'R,6'S,8'R)-6'-methylspiro[1,3-dioxolane-2,5'-9,12-dioxatricyclo[6.3.1.01,6]dodec-10-ene]-2'-yl]oxysilane
• CAS: 935528-83-9
• 化学式: C₁₉H₃₂O₅Si
• 分子量: 368.546
• InChiKey: WXGWXTGAJIJNDP-LMSBXDPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-dimethyl-[(1'R,2'R,6'S,8'R)-6'-methylspiro[1,3-dioxolane-2,5'-9,12-dioxatricyclo[6.3.1.01,6]dodec-10-ene]-2'-yl]oxysilane 在 双(乙腈)氯化钯(II) 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以80%的产率得到C₁₇H₂₈O₄Si
  参考文献：
  名称：

  高度取代和立体定义的顺式稠合内酯的高效构建

  摘要：

  本文描述的方法涉及环状烯-缩醛的环氧化反应，以自发生成 6α-羟基-双-缩醛，可作为 Cannizzaro 型重排的前体，产生双角取代的顺式稠合内酯。氧化剂，m-CPBA 或 NaBO 3 ，以及取代模式在确定环氧化/开环顺序的过程中都很重要，NaBO 3 是环氧化/自发开环/环的理想亲电氧化剂-系统交换序列。

  DOI：

  10.1002/ejoc.201000556
• 作为产物：
  描述：

  C₁₉H₃₄O₅Si 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以72%的产率得到tert-butyl-dimethyl-[(1'R,2'R,6'S,8'R)-6'-methylspiro[1,3-dioxolane-2,5'-9,12-dioxatricyclo[6.3.1.01,6]dodec-10-ene]-2'-yl]oxysilane
  参考文献：
  名称：

  Enantioselective Total Synthesis of 1-epi-Pathylactone A

  摘要：

  The first enantioselective total synthesis of 1-epi-pathylactone A, 3, has been accomplished using a PhI(OAc)(2)-mediated domino reaction as a key step. No diastereomeric separation was required throughout the whole synthetic scheme presented in this paper. Comparison of H-1 and C-13 NMR spectral data of the synthetic product with the reported spectral data of natural pathylactone A, coupled with an X-ray crystallographic analysis, led to the conclusion that the C1 configuration in the original paper was erroneously ascribed to (R).

  DOI：

  10.1021/ol070207y

文献信息

• Efficient Construction of Highly Substituted and Stereodefined cis-Fused Lactones
  作者：Zobida Elkhayat、Imad Safir、Zoila Gandara、Pascal Retailleau、Siméon Arseniyadis

  DOI：10.1002/ejoc.201000556

  日期：2010.9

  ene-acetals to spontaneously generate 6α-hydroxy-bis-acetals that could serve as precursors for a Cannizzaro-type rearrangement, yielding bis-angularly substituted cis-fused lactones. Both the oxidizing reagent, m-CPBA or NaBO 3 , and the substitution pattern can be important in determining the course of the epoxidation/ring-opening sequence, with NaBO 3 being the ideal electrophilic oxidant for the

  本文描述的方法涉及环状烯-缩醛的环氧化反应，以自发生成 6α-羟基-双-缩醛，可作为 Cannizzaro 型重排的前体，产生双角取代的顺式稠合内酯。氧化剂，m-CPBA 或 NaBO 3 ，以及取代模式在确定环氧化/开环顺序的过程中都很重要，NaBO 3 是环氧化/自发开环/环的理想亲电氧化剂-系统交换序列。
• Enantioselective Total Synthesis of 1-<i>epi</i>-Pathylactone A
  作者：Angéline Chanu、Imad Safir、Ramkrishna Basak、Angèle Chiaroni、Siméon Arseniyadis

  DOI：10.1021/ol070207y

  日期：2007.3.1

  The first enantioselective total synthesis of 1-epi-pathylactone A, 3, has been accomplished using a PhI(OAc)(2)-mediated domino reaction as a key step. No diastereomeric separation was required throughout the whole synthetic scheme presented in this paper. Comparison of H-1 and C-13 NMR spectral data of the synthetic product with the reported spectral data of natural pathylactone A, coupled with an X-ray crystallographic analysis, led to the conclusion that the C1 configuration in the original paper was erroneously ascribed to (R).