(3aR,6aR)-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one | 1009810-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6aR)-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one
• 英文别名: (3aR,6aR)-spiro[3a,6a-dihydrocyclopenta[d][1,3]dioxole-2,1'-cyclopentane]-4-one
• CAS: 1009810-89-2
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: USEVRWFFBXFSAI-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,6aR)-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one 在 咪唑 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 copper(I) bromide dimethylsulfide complex 、 cerium(III) chloride heptahydrate 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 sodium hydride 、 氯化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 36.5h， 生成 (1R,2R,3R,5S)-2-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-3-vinylcyclopentyl 2-chloroacetate
  参考文献：
  名称：

  2′-Fluoro-3-deazaaristeromycin

  摘要：

  The carbocyclic nucleoside 3-deazaaristeromycin has shown biological promise but a library of its derivatives upon which to expand this property is lacking. To address this situation, the synthesis of the two diastereomers of 2'-fluoro-3-deazaaristeromycin is described in a multistep convergent process that calls upon D-ribose for construction of the cyclopentyl fluoro units. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.023
• 作为产物：
  描述：

  (2R,3R)-3-vinyl-1,4-dioxaspiro[4.4]nonane-2-carbaldehyde 在 Grubbs catalyst first generation 、 manganese(IV) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (3aR,6aR)-3aH-spiro[cyclopenta[d][1,3]dioxole-2,1'-cyclopentan]-4(6aH)-one
  参考文献：
  名称：

  2′-Fluoro-3-deazaaristeromycin

  摘要：

  The carbocyclic nucleoside 3-deazaaristeromycin has shown biological promise but a library of its derivatives upon which to expand this property is lacking. To address this situation, the synthesis of the two diastereomers of 2'-fluoro-3-deazaaristeromycin is described in a multistep convergent process that calls upon D-ribose for construction of the cyclopentyl fluoro units. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.023

文献信息

• 5′-Fluoro-5′-deoxyaristeromycin
  作者：Weikuan Li、Xueqiang Yin、Stewart W. Schneller

  DOI：10.1016/j.bmcl.2007.10.095

  日期：2008.1

  5'-Fluoro-5'-deoxyaristeromycin (2) has been prepared via a Mitsunobu coupling of (1S,2S,3R,4S)-2,3-(cyclopentylidenedioxy)-4-fluoromethylcyclopentan-1-ol with N-6-bis-boc protected adenine. This procedure is adaptable to preparing a number of 5'-fluoro-5'-deoxycarbocyclic nucleoside analogs with diversity in the heterocyclic base. Antiviral analysis found promising activity for 2 toward measles but no other viruses. No cytotoxicity was observed for 2. (C) 2007 Elsevier Ltd. All rights reserved.
• A CONVENIENT SYNTHESIS OF THE L-LIKE ENANTIOMER OF 4'-METHYL-3-dEAZAARISTEROMYCIN
  作者：Stewart W. Schneller、Chun Chen、Wei Ye

  DOI：10.3987/com-12-s(n)20

  日期：——

  As an entry into L-like 3-deazaaristeromycins, synthesis of the enantiomer of D-like 4'-methyl-3-deazaaristeromycin is described in 11 steps from a readily accessible cyclopentenone that, in turn, is prepared from D-ribose.