(-)-menthyl γ-benzyloxyacetoacetate | 415678-69-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-menthyl γ-benzyloxyacetoacetate
• 英文别名: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-(benzyloxy)-3-oxobutanoate
• CAS: 415678-69-2
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: AHHAMKGCEDYVRN-LSTHTHJFSA-N

物化性质

• 沸点：
  454.2±25.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-menthyl γ-benzyloxyacetoacetate 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 以92%的产率得到(-)-menthyl γ-benzyloxy-α-diazo-β-ketoester
  参考文献：
  名称：

  Ruthenium(II) Porphyrin Catalyzed Formation of (Z)-4-Alkyloxycarbonyl- methylidene-1,3-dioxolanes from γ-Alkoxy-α-diazo-β-ketoesters

  摘要：

  [GRAPHICS]Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of gamma-alkoxy-alpha-diazo-beta-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [Ru-II(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.

  DOI：

  10.1021/ol010283f
• 作为产物：
  描述：

  苯甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 生成 (-)-menthyl γ-benzyloxyacetoacetate
  参考文献：
  名称：

  Ruthenium(II) Porphyrin Catalyzed Formation of (Z)-4-Alkyloxycarbonyl- methylidene-1,3-dioxolanes from γ-Alkoxy-α-diazo-β-ketoesters

  摘要：

  [GRAPHICS]Ruthenum(II) porphyrins and dirhodium(II) acetate catalyze cyclization of gamma-alkoxy-alpha-diazo-beta-ketoesters to (Z)-4-(alkyloxycarbonylmethylidene)-1,3-dioxolanes selectively (ca. 68% yield) with no formation of 3(2H)-furanones. Reacting a diazo ketoester with [Ru-II(TTP)(CO)] [H2TTP = meso-tetrakis(p-tolyl) porphyrin] in toluene afforded a ruthenium carbenoid complex, which has been isolated and spectroscopically characterized. A mechanism involving hydrogen atom migration from the C-H bond to the ruthenium carbenoid is proposed.

  DOI：

  10.1021/ol010283f

文献信息

• anti-Selective aldol reactions of chiral alcohol substituted γ-benzyloxyl vinylogous urethanes and the synthesis of 3-benzyloxyl-4-hydroxylalkan-2-ones
  作者：Yu-Jang Li、Chuan-Chung Chung、Pin-Zu Chen

  DOI：10.1016/j.tetasy.2017.10.003

  日期：2017.11

  The anti-selective aldol reaction of chiral alcohol-substituted gamma-benzyloxy vinylogous urethanes is described. The use of (1S,2R,4R)-1-(hydroxydiphenylmethyl)-7,7-dimethylbicyclo[2,2,1]-heptan-2-ol as a chiral auxiliary in the aldol reaction of a vinylogous urethane enolate was found to provide anti-products in good yields with moderate to excellent enantioselectivities. The major anti-vinylogous urethane lactones were transformed into 3-benzyloxyl-4-hydroxylalkan-2-ones in good yields. (C) 2017 Elsevier Ltd. All rights reserved.