(8'aS)-3',8'a-dimethylspiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2',3'-diol | 351330-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8'aS)-3',8'a-dimethylspiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2',3'-diol
• CAS: 351330-58-0
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: NSOADSFFZABOIT-CPCZMJQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8'aS)-3',8'a-dimethylspiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2',3'-diol 在 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 3.5h， 生成 (8aS)-7-butyl-6,8a-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：

  (8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene 以 四氢呋喃 、 苯 为溶剂， 反应 99.5h， 生成 (8'aS)-3',8'a-dimethylspiro[1,3-dioxolane-2,8'-2,5,6,7-tetrahydro-1H-naphthalene]-2',3'-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

文献信息

• Mild Protocols for Generating Molecular Complexity: A Comparative Study of Hetero-Domino Reactions Based on the Oxidant and the Substitution Pattern
  作者：José I. Candela Lena、Elena M. Sánchez Fernández、Alwar Ramani、Nicolas Birlirakis、Alejandro F. Barrero、Siméon Arseniyadis

  DOI：10.1002/ejoc.200400549

  日期：2005.2

  A bicyclic unsaturated 1,2-diol framework was found to undergo an interesting set of domino reactions on treatment with oxidants. One-pot syntheses of seven-membered-ringcontaining frameworks were achieved by a Pb(OAc)4-mediated domino process, while with other oxidants investigated, such as Mn(OAc)3, Dess–Martin periodinane, PhI(OAc)2, Ph3Bi(CO)3, NaIO4, and NaBiO3, the domino process was interrupted

  发现双环不饱和 1,2-二醇骨架在用氧化剂处理时会发生一组有趣的多米诺骨牌反应。通过 Pb(OAc)4 介导的多米诺过程实现了含七元环骨架的一锅法合成，同时研究了其他氧化剂，如 Mn(OAc)3、Dess-Martin periodinane、PhI(OAc)2、 Ph3Bi(CO)3、NaIO4 和 NaBiO3，多米诺骨牌过程中途中断。最后，四丙基过钌酸铵 (TPAP-NMO)、Pd(OAc)2、重铬酸吡啶鎓 (PDC) 和氯铬酸吡啶鎓 (PCC) 仅产生烯丙基氧化和进一步的二酮形成，而没有任何引发多米诺骨牌所需的键断裂
• Tandem glycol cleavage—intramolecular 4+2 cycloadditions mediated by Mn(OAc)3
  作者：José Ignacio Candela Lena、Maria del Rosario Rico Ferreira、José Ignacio Martı́n Hernando、Ertan Altınel、Siméon Arseniyadis

  DOI：10.1016/s0040-4039(01)00396-3

  日期：2001.4
• Lena, Jose Ignacio Candela; Hernando, Jose Ignacio Martin; Ferreira, Maria del Rosario Rico, Synlett, 2001, # 5, p. 597 - 600
  作者：Lena, Jose Ignacio Candela、Hernando, Jose Ignacio Martin、Ferreira, Maria del Rosario Rico、Altinel, Ertan、Arseniyadis, Simeon

  DOI：——

  日期：——
• The domino chemistry approach to molecular complexity: high-yielding bis-hetero intramolecular Diels–Alder reactions with ketone components
  作者：Angeline Chanu、Isabel Castellote、Aurelien Commeureuc、Imad Safir、Siméon Arseniyadis

  DOI：10.1016/j.tetasy.2006.09.003

  日期：2006.10

  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.