(+/-)-(1R*,2R*)-3,3,4-trimethylcyclohex-4-ene-1,2-dicarboxylic acid | 91352-95-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-(1R*,2R*)-3,3,4-trimethylcyclohex-4-ene-1,2-dicarboxylic acid
• 英文别名: 3,3,4-Trimethyl-cyclohex-4-en-dicarbonsaeure-(1r,2c)；3,3,4-Trimethyl-4-cyclohexen-1.2-cis-dicarbonsaeure；(1R,2R)-3,3,4-trimethylcyclohex-4-ene-1,2-dicarboxylic acid
• CAS: 91352-95-3
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: QLMWSDFQVJQTRA-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-(1R*,2R*)-3,3,4-trimethylcyclohex-4-ene-1,2-dicarboxylic acid 生成 3,3,4-Trimethyl-cyclohex-4-en-dicarbonsaeure-(1r,2c)-diethylester
  参考文献：
  名称：

  Stereochemistry Related to the Diels-Alder Adducts of 4-Methyl-1,3-pentadienes

  摘要：

  DOI：

  10.1246/bcsj.37.432
• 作为产物：
  描述：

  4,4,5-trimethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione 在 sodium carbonate 作用下， 反应 2.0h， 以81%的产率得到(+/-)-(1R*,2R*)-3,3,4-trimethylcyclohex-4-ene-1,2-dicarboxylic acid
  参考文献：
  名称：

  New preparation of (3aR*,6S*,7aR*)-6,7,7-trimethylhexahydro-2-benzofuran-1(3H)-one: formal synthesis of (±)-γ-irone

  摘要：

  A four-step synthesis of (3aR*,6S*,7aR*)-6,7.7-trimethylhexahydro-2-benzofuran-1(3H)-one 2 has been developed. Lactone 2 is an intermediate in a synthesis of gamma -irone. Opening of the Diels-Alder adduct 5 with ethanol afforded hemiester 6b with 87:13 regioselectivity. Subsequent chemoselective reduction of the ester group in 6b yielded hydroxyacid 14 which was lactonized to the cis-fused bicyclic lactone 15. Finally, hydrogenation of 15 into 2 occured with complete diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01059-0

文献信息

• Stereochemistry Related to the Diels-Alder Adducts of 4-Methyl-1,3-pentadienes
  作者：Iwao Ichikizaki、Atsuaki Arai

  DOI：10.1246/bcsj.37.432

  日期：1964.3
• New preparation of (3aR*,6S*,7aR*)-6,7,7-trimethylhexahydro-2-benzofuran-1(3H)-one: formal synthesis of (±)-γ-irone
  作者：Pascal Gosselin、Angélique Perrotin、Stéphane Mille

  DOI：10.1016/s0040-4020(00)01059-0

  日期：2001.1

  A four-step synthesis of (3aR*,6S*,7aR*)-6,7.7-trimethylhexahydro-2-benzofuran-1(3H)-one 2 has been developed. Lactone 2 is an intermediate in a synthesis of gamma -irone. Opening of the Diels-Alder adduct 5 with ethanol afforded hemiester 6b with 87:13 regioselectivity. Subsequent chemoselective reduction of the ester group in 6b yielded hydroxyacid 14 which was lactonized to the cis-fused bicyclic lactone 15. Finally, hydrogenation of 15 into 2 occured with complete diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

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