(3aR,5S,6aR)-5-(2-Chloro-allyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid methyl ester | 210299-65-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3aR,5S,6aR)-5-(2-Chloro-allyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid methyl ester
• 英文别名: methyl (3aR,5S,6aR)-5-(2-chloroprop-2-enyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-5-carboxylate
• CAS: 210299-65-3
• 化学式: C₁₂H₁₇ClO₅
• 分子量: 276.717
• InChiKey: SDJGUBUGOLMBNL-VDDIYKPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6aR)-5-(2-Chloro-allyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 二异丁基氢化铝 、 三苯基膦 、 methyloxirane 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 0.25h， 生成 (3aR,5S,6aR)-2,2-dimethylspiro[6,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-5,4'-cyclopent-2-ene]-1'-one
  参考文献：
  名称：

  A carbohydrate approach to 4-hydroxy-2-cyclopentenone moiety of antitumor prostanoid Punaglandin IV via alkylation of ester uronate

  摘要：

  An efficient and stereoselective synthesis of a chiral precursor of 2-chloro-4-hydroxy-4-alkyl-2-cyclopentenone has been realized by alkylation of a sugar methyl uronate derived from 1,2-O-isopropylidene alpha-D-glucose with an acetonyl equivalent, and subsequent intramolecular Wittig reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00694-7
• 作为产物：
  描述：

  (-)-(3aR,5R,6aR)-methyl 3a,5,6,6a-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carboxylate 、 2-氯-3-碘丙-1-烯 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到(3aR,5S,6aR)-5-(2-Chloro-allyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  A carbohydrate approach to 4-hydroxy-2-cyclopentenone moiety of antitumor prostanoid Punaglandin IV via alkylation of ester uronate

  摘要：

  An efficient and stereoselective synthesis of a chiral precursor of 2-chloro-4-hydroxy-4-alkyl-2-cyclopentenone has been realized by alkylation of a sugar methyl uronate derived from 1,2-O-isopropylidene alpha-D-glucose with an acetonyl equivalent, and subsequent intramolecular Wittig reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00694-7

文献信息

• A carbohydrate approach to 4-hydroxy-2-cyclopentenone moiety of antitumor prostanoid Punaglandin IV via alkylation of ester uronate
  作者：Cyrille Kuhn、Jean-Claude Florent

  DOI：10.1016/s0040-4039(98)00694-7

  日期：1998.6

  An efficient and stereoselective synthesis of a chiral precursor of 2-chloro-4-hydroxy-4-alkyl-2-cyclopentenone has been realized by alkylation of a sugar methyl uronate derived from 1,2-O-isopropylidene alpha-D-glucose with an acetonyl equivalent, and subsequent intramolecular Wittig reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.