(1R,2R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethyl-1-naphthalene-propanal | 924884-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethyl-1-naphthalene-propanal
• 英文别名: 3-[(1R,2R,4aS,8aS)-2-(methoxymethoxy)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]propanal
• CAS: 924884-74-2
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: QGJLOALIDZQCJK-OGWHTMIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethyl-1-naphthalene-propanal 、 (S)-2,2-dimethyl-1-[3'-(benzothiazole-2''-sulfonyl)butyl]-6-methylenecyclohexane 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以52%的产率得到
  参考文献：
  名称：

  New total synthesis of (+)-ambrein

  摘要：

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.015
• 作为产物：
  描述：

  (1R,2R,4aS,8aS)-(+)-2-hydroxy-1,2,3,4,4a,5,6,7,8,8a-decahydro-2,5,5,8a-tetramethyl-naphthalen-1-aldehyde 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 florisil 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 氢气 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 37.0h， 生成 (1R,2R,4aS,8aS)-(-)-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-(methoxymethyloxy)-2,5,5,8a-tetramethyl-1-naphthalene-propanal
  参考文献：
  名称：

  New total synthesis of (+)-ambrein

  摘要：

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.015

文献信息

• New total synthesis of (+)-ambrein
  作者：Naoko Fujiwara、Masako Kinoshita、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2006.11.015

  日期：2006.11

  The convergent synthesis of (+)-ambrein 1 was achieved based on a modified Julia coupling reaction between aldehyde 14 corresponding to the left-half A and sulfone 25a or 25b corresponding to the right-half B. Aldehyde 14 was synthesized in 14% overall yield (nine steps) from the enzymatic resolution product, epoxy alcohol (8aS)-2. Sulfone 25a or 25b was synthesized in 11 steps (25a: 41% overall yield, 25b: 56% overall yield) from the enzymatic resolution product, (1S,6S)-2,2-dimethyl-6-hydroxyhexane-l-carboxylate 4. (c) 2006 Elsevier Ltd. All rights reserved.