(4R,8aR)-4-((tert-butyldimethylsilyl)oxy)-6-hydroxy-6,8a-dimethyl-8-methylene-2,3,4,6,8,8a-hexahydro-7H-spiro[naphthalene-1,2'-[1,3]dioxolan]-7-one | 917478-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,8aR)-4-((tert-butyldimethylsilyl)oxy)-6-hydroxy-6,8a-dimethyl-8-methylene-2,3,4,6,8,8a-hexahydro-7H-spiro[naphthalene-1,2'-[1,3]dioxolan]-7-one
• CAS: 917478-73-0
• 化学式: C₂₁H₃₄O₅Si
• 分子量: 394.583
• InChiKey: RXIFPEUYWMXEMH-VBHUFULTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R,8aR)-4-((tert-butyldimethylsilyl)oxy)-6-hydroxy-6,8a-dimethyl-8-methylene-2,3,4,6,8,8a-hexahydro-7H-spiro[naphthalene-1,2'-[1,3]dioxolan]-7-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 (4R,8aS)-4-((tert-butyldimethylsilyl)oxy)-6,8a-dimethyl-8-methylene-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 、 正丁基锂 、 双氧水 、 甲基三氧化铼(VII) 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.17h， 生成 (4R,8aR)-4-((tert-butyldimethylsilyl)oxy)-6-hydroxy-6,8a-dimethyl-8-methylene-2,3,4,6,8,8a-hexahydro-7H-spiro[naphthalene-1,2'-[1,3]dioxolan]-7-one
  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