ethyl 3-hydroxy-5-methylcyclohexene-4-carboxylate | 148441-23-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 3-hydroxy-5-methylcyclohexene-4-carboxylate
• 英文别名: Ethyl 2-hydroxy-6-methylcyclohex-3-ene-1-carboxylate
• CAS: 148441-23-0
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: YVBYPDMIIHHQTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-5-methylcyclohexene-4-carboxylate 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate

  摘要：

  An expeditious asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-enecarboxylate has been achieved in four steps in 42% overall yield employing as the key step a domino reaction initiated by a highly diastereoselective lithium amide 1,4-conjugate addition to a nona-2,7-diendioic diester followed by a 6-exo-trig cyclisation of the thus formed enolate. Cope elimination protocol of the cyclic adduct affords, depending on the lithium amide used, the corresponding nitro-compound or the expected cyclohexene derivative. The methyl group attached to the cyclohexane ring is achieved by selective ester hydrolysis and subsequent Barton decarboxylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.048
• 作为产物：
  描述：

  6-甲基-2-环己酮-3-烯-1-甲酸乙酯 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 以98%的产率得到ethyl 3-hydroxy-5-methylcyclohexene-4-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate

  摘要：

  An expeditious asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-enecarboxylate has been achieved in four steps in 42% overall yield employing as the key step a domino reaction initiated by a highly diastereoselective lithium amide 1,4-conjugate addition to a nona-2,7-diendioic diester followed by a 6-exo-trig cyclisation of the thus formed enolate. Cope elimination protocol of the cyclic adduct affords, depending on the lithium amide used, the corresponding nitro-compound or the expected cyclohexene derivative. The methyl group attached to the cyclohexane ring is achieved by selective ester hydrolysis and subsequent Barton decarboxylation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.048

文献信息

• Herbicidal substituted cycloalkenes
  申请人：Bayer Aktiengesellschaft

  公开号：US05284820A1

  公开（公告）日：1994-02-08

  Herbicidal substituted cycloalkenes of the formula ##STR1## in which A is a straight-chain or branched, optionally substituted alkanediyl group, X is O, S, N--R.sup.8 or CR.sup.9 R.sup.10, Y is O, S, NH or N-alkyl, Z is N or R.sup.11, and R.sup.1 to R.sup.11 represent various organic radicals.

  公式为##STR1##的除草取代环烷烯，其中A是直链或支链，可选取代的烷基二基团，X为O，S，N-R.sup.8或CR.sup.9 R.sup.10，Y为O，S，NH或N-烷基，Z为N或R.sup.11，R.sup.1至R.sup.11代表各种有机基团。
• US5284820A
  申请人：——

  公开号：US5284820A

  公开（公告）日：1994-02-08