[(5'R,8'aS)-5'-[tert-butyl(dimethyl)silyl]oxy-8'a-methyl-3'-oxospiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2'-yl] acetate | 917478-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(5'R,8'aS)-5'-[tert-butyl(dimethyl)silyl]oxy-8'a-methyl-3'-oxospiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2'-yl] acetate
• CAS: 917478-39-8
• 化学式: C₂₁H₃₄O₆Si
• 分子量: 410.583
• InChiKey: MHIDDZQYBAWRIQ-IKCNDWCXSA-N

物化性质

• 熔点：
  132-135 °C
• 沸点：
  470.0±45.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(5'R,8'aS)-5'-[tert-butyl(dimethyl)silyl]oxy-8'a-methyl-3'-oxospiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2'-yl] acetate 在 正丁基锂 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二甲基亚砜 为溶剂， 反应 5.67h， 生成 (4R,8aS)-4-((tert-butyldimethylsilyl)oxy)-6-((methoxymethoxy)methyl)-7,8a-dimethyl-3,4,6,7,8,8a-hexahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolane]-6,7-diol
  参考文献：
  名称：

  The domino chemistry approach to molecular complexity: high-yielding bis-hetero intramolecular Diels–Alder reactions with ketone components

  摘要：

  The bis-keto-hetero-IMDA option, with two ketone components (both the heterodiene and heterodienophile moieties) has been examined in several representative domino templates with the aim of ultimately developing efficient methods for the synthesis of structurally complex natural products. The domino sequence could also be activated efficiently by utilizing the less toxic iodobenzene diacetate as the oxidative cleavage/[4+2] promoter while it is unbiased to the nature of substitution around the bicyclic framework. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.003
• 作为产物：
  描述：

  [(8'aS)-8'a-methyl-3'-oxospiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2'-yl] acetate 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 双氧水 、 甲基三氧化铼(VII) 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 [(5'R,8'aS)-5'-[tert-butyl(dimethyl)silyl]oxy-8'a-methyl-3'-oxospiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2'-yl] acetate
  参考文献：
  名称：

  The domino chemistry approach to molecular complexity: high-yielding bis-hetero intramolecular Diels–Alder reactions with ketone components

  摘要：

  The bis-keto-hetero-IMDA option, with two ketone components (both the heterodiene and heterodienophile moieties) has been examined in several representative domino templates with the aim of ultimately developing efficient methods for the synthesis of structurally complex natural products. The domino sequence could also be activated efficiently by utilizing the less toxic iodobenzene diacetate as the oxidative cleavage/[4+2] promoter while it is unbiased to the nature of substitution around the bicyclic framework. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.003

文献信息

• 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).