[(3aS,6S,7R,7aS)-2,2-dimethyl-6-[(4-methylphenyl)methoxy]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] prop-2-enoate | 178680-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: [(3aS,6S,7R,7aS)-2,2-dimethyl-6-[(4-methylphenyl)methoxy]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] prop-2-enoate
• CAS: 178680-25-6
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: FMSPSLATUDPNTI-OWLYRPNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3aS,6S,7R,7aS)-2,2-dimethyl-6-[(4-methylphenyl)methoxy]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] prop-2-enoate 、 天然橡胶 在 二氯乙基铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (R)-4-Methyl-cyclohex-3-enecarboxylic acid (3aS,6S,7R,7aS)-2,2-dimethyl-6-(4-methyl-benzyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 、 (S)-4-Methyl-cyclohex-3-enecarboxylic acid (3aS,6S,7R,7aS)-2,2-dimethyl-6-(4-methyl-benzyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
  参考文献：
  名称：

  Sugarometallic chemistry: Aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction

  摘要：

  The diastereoselectivity of the the Diels-Alder reaction of eta(6)-(4'-methylbenzyl 2-O-Acryloyl-3,4-O-isopropylidene-beta-L-arabinopyranoside) tricarbonylchromium(O) 5 with isoprene, butadiene, cyclopentadiene, and furan were studied, and the best selectivity was 95:5 (with isoprene), whereas the diastereoselectivity of the same reaction with the noncomplexed chiral auxiliary-acrylate 6 was only 78:22. The absolute configuration of the newly generated stereogenic center was Sound to be R in each case. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00648-x
• 作为产物：
  描述：

  L-(+)-arabinose 在 盐酸 、 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 85.0h， 生成 [(3aS,6S,7R,7aS)-2,2-dimethyl-6-[(4-methylphenyl)methoxy]-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl] prop-2-enoate
  参考文献：
  名称：

  Sugarometallic chemistry: Aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction

  摘要：

  The diastereoselectivity of the the Diels-Alder reaction of eta(6)-(4'-methylbenzyl 2-O-Acryloyl-3,4-O-isopropylidene-beta-L-arabinopyranoside) tricarbonylchromium(O) 5 with isoprene, butadiene, cyclopentadiene, and furan were studied, and the best selectivity was 95:5 (with isoprene), whereas the diastereoselectivity of the same reaction with the noncomplexed chiral auxiliary-acrylate 6 was only 78:22. The absolute configuration of the newly generated stereogenic center was Sound to be R in each case. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00648-x

文献信息

• Sugarometallic chemistry: Aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction
  作者：Tony K.M. Shing、Hak-Fun Chow、Ivan H.F. Chung

  DOI：10.1016/0040-4039(96)00648-x

  日期：1996.5

  The diastereoselectivity of the the Diels-Alder reaction of eta(6)-(4'-methylbenzyl 2-O-Acryloyl-3,4-O-isopropylidene-beta-L-arabinopyranoside) tricarbonylchromium(O) 5 with isoprene, butadiene, cyclopentadiene, and furan were studied, and the best selectivity was 95:5 (with isoprene), whereas the diastereoselectivity of the same reaction with the noncomplexed chiral auxiliary-acrylate 6 was only 78:22. The absolute configuration of the newly generated stereogenic center was Sound to be R in each case. Copyright (C) 1996 Elsevier Science Ltd