(7R,11S)-7,11-bis(1,3-benzodioxol-5-yl)-3,3-dimethyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione | 627106-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (7R,11S)-7,11-bis(1,3-benzodioxol-5-yl)-3,3-dimethyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione
• CAS: 627106-81-4
• 化学式: C₂₅H₂₂O₉
• 分子量: 466.444
• InChiKey: AOPBLNYWQQYUGB-CALCHBBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (7R,11S)-7,11-bis(1,3-benzodioxol-5-yl)-3,3-dimethyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione 在 L-Selectride 、 亚硝基苯 、 L-脯氨酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 (7S,8R,9R,11R)-8,9-dihydroxy-3,3-dimethyl-7,11-bis-benzo[1,3]dioxol-5-yl-2,4-dioxa-spiro[5.5]undecane-1,5-dione
  参考文献：
  名称：

  Direct Amino Acid-Catalyzed Asymmetric Desymmetrization of meso-Compounds:  Tandem Aminoxylation/O−N Bond Heterolysis Reactions

  摘要：

  A practical organocatalytic process for the synthesis of optically active, highly substituted (x-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O-N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O-N bond reduced products as single diastereomers with good yields and excellent enantiomeric excesses.

  DOI：

  10.1021/ol050246e
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 1,2-bis(benzo[d][1,3]dioxol-5-ylmethylene)hydrazine 在 溶剂黄146 作用下， 反应 4.0h， 以84%的产率得到(7R,11S)-7,11-bis(1,3-benzodioxol-5-yl)-3,3-dimethyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione
  参考文献：
  名称：

  A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes

  摘要：

  描述了一种新颖的烯胺与梅尔德鲁姆酸的多米诺自催化反应。在这一反应中，在酸性条件下成功合成了一系列具有显著非对映选择性的多环螺[5.5]十一烷-1,5,9-三酮和双螺[4.2.5.2]十五烷-9,13-二酮衍生物，最多形成六个新键，同时伴随着烯胺的CN键断裂和梅尔德鲁姆酸的分解，副产物乙酰肼作为新型自催化剂。

  DOI：

  10.1039/b822645h

文献信息

• Organocatalytic Asymmetric Domino Knoevenagel/Diels–Alder Reactions: A Bioorganic Approach to the Diastereospecific and Enantioselective Construction of Highly Substituted Spiro[5,5]undecane-1,5,9-triones
  作者：D. B. Ramachary、Naidu S. Chowdari、Carlos F. Barbas

  DOI：10.1002/anie.200351916

  日期：2003.9.15
• A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes
  作者：Bo Jiang、Wen-Juan Hao、Jin-Peng Zhang、Shu-Jiang Tu、Feng Shi

  DOI：10.1039/b822645h

  日期：——

  A new domino autocatalytic reaction of imines with Meldrum's acid was described. In this reaction, a series of polycyclic spiro[5.5]undecane-1,5,9-trione and dispiro[4.2.5.2]pentadecane-9,13-dione derivatives, with remarkable diastereoselectivity, were successfully synthesized in acidic condition, and up to six new bonds were formed accompanied by the CN bond cleavage of the imines and the decomposition of Meldrum's acid, with by-product of acetohydrazide as a novel autocatalyst.

  描述了一种新颖的烯胺与梅尔德鲁姆酸的多米诺自催化反应。在这一反应中，在酸性条件下成功合成了一系列具有显著非对映选择性的多环螺[5.5]十一烷-1,5,9-三酮和双螺[4.2.5.2]十五烷-9,13-二酮衍生物，最多形成六个新键，同时伴随着烯胺的CN键断裂和梅尔德鲁姆酸的分解，副产物乙酰肼作为新型自催化剂。
• Direct Amino Acid-Catalyzed Asymmetric Desymmetrization of <i>meso</i>-Compounds:  Tandem Aminoxylation/O−N Bond Heterolysis Reactions
  作者：Dhevalapally B. Ramachary、Carlos F. Barbas

  DOI：10.1021/ol050246e

  日期：2005.4.14

  A practical organocatalytic process for the synthesis of optically active, highly substituted (x-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O-N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O-N bond reduced products as single diastereomers with good yields and excellent enantiomeric excesses.