(1S,2R,5S,8aS)-2,5-Dimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde | 275825-02-0

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (1S,2R,5S,8aS)-2,5-Dimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde
• 英文别名: (1S,2R,5S,8aS)-2,5-dimethyl-5-(4-methylpent-4-enyl)-2,3,6,7,8,8a-hexahydro-1H-naphthalene-1-carbaldehyde
• CAS: 275825-02-0
• 化学式: C₁₉H₃₀O
• 分子量: 274.447
• InChiKey: KCFIEEGNGWGXLL-VUHPKUFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S,8aS)-2,5-Dimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde 在 sodium tetrahydroborate 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 生成 Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester
  参考文献：
  名称：

  Concise asymmetric synthesis of dysidiolide

  摘要：

  The cdc25A protein phosphatase inhibitor dysidiolide (1) has been synthesized via intermolecular Diels-Alder reaction of the triene 4 with crotonaldehyde and construction of a quaternary carbon center by methylation of the exocyclic enolate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00078-2
• 作为产物：
  描述：

  (S)-6-methyl-6-(4-methylbenzenesulfonyloxypropyl)-1,4-dioxaspiro[4.5]decane 在 copper(l) iodide 、 二氯乙基铝 aluminium hydride 、 N-甲基吲哚酮 、 cerium(III) chloride 、 四丙基高钌酸铵 、 4-甲基苯磺酸吡啶 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 (1S,2R,5S,8aS)-2,5-Dimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalene-1-carbaldehyde
  参考文献：
  名称：

  Concise asymmetric synthesis of dysidiolide

  摘要：

  The cdc25A protein phosphatase inhibitor dysidiolide (1) has been synthesized via intermolecular Diels-Alder reaction of the triene 4 with crotonaldehyde and construction of a quaternary carbon center by methylation of the exocyclic enolate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00078-2

文献信息

• Concise asymmetric synthesis of dysidiolide
  作者：Masato Takahashi、Kosuke Dodo、Yuichi Hashimoto、Ryuichi Shirai

  DOI：10.1016/s0040-4039(00)00078-2

  日期：2000.3

  The cdc25A protein phosphatase inhibitor dysidiolide (1) has been synthesized via intermolecular Diels-Alder reaction of the triene 4 with crotonaldehyde and construction of a quaternary carbon center by methylation of the exocyclic enolate. (C) 2000 Elsevier Science Ltd. All rights reserved.