(S)-2-(1,4-dioxaspiro[4.5]-decan-2-yl)pent-4-enal | 1231913-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2-(1,4-dioxaspiro[4.5]-decan-2-yl)pent-4-enal
• 英文别名: 2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)pent-4-enal；2-[(3S)-1,4-dioxaspiro[4.5]decan-3-yl]pent-4-enal
• CAS: 1231913-19-1
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: UAGNLEOEMALMDG-PIJUOVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  (S)-2-(1,4-dioxaspiro[4.5]-decan-2-yl)pent-4-enal 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.75h， 生成 (S)-2-((S)-1,4-dioxaspiro[4.5]decan-2-yl)pent-4-enal
  参考文献：
  名称：

  以手性4-戊烯醇衍生物为结构单元的阿尔茨海默氏病治疗药（R）-（-）和（S）-（+）-金刚烷酸的立体发散方法

  摘要：

  从手性和非手性材料都已经实现了抗阿尔茨海默病药物（R）-（-）和（S）-（+）-金刚烷酸的有效立体发散性全合成。该策略的特征是采用脯氨酸催化的不对称α-氨基氧基化和[3,3]σ克莱森重排的可分离非对映体C-2手性4-戊烯醇中间体的有效方法是本合成的重点。

  DOI：

  10.1016/j.tet.2017.03.002
• 作为产物：
  描述：

  (S)-2-(2-(allyloxy)-vinyl)-1,4-dioxospiro[4.5]-decane 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以97%的产率得到(S)-2-(1,4-dioxaspiro[4.5]-decan-2-yl)pent-4-enal
  参考文献：
  名称：

  The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers

  摘要：

  The stereoselective synthesis of all the possible stereoisomers of bis-tetrahydrofyran alcohol, a ligand used for obtaining HIV protease inhibitors including Darunavir 1 and Brecanavir 2 has been achieved. A key intermediate 4-pentenal 5 was obtained by employing a Wittig olefination-Claisen rearrangement protocol from D-glyceraldehyde derivative 3 as a source of chirality. The 4-pentenal was readily converted in the bis-THF alcohol moiety in three steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.005

文献信息

• A stereodivergent approach to carbahexofuranoses: synthesis of carba-α-d-glucofuranose, carba-β-d-altrofuranose, carba-α-d-allofuranose, carba-β-d-idofuranose, carba-α-d-galactofuranose and carba-β-d-talofuranose
  作者：Mukund G. Kulkarni、Ajit S. Borhade、Yunnus B. Shaikh、Attrimuni P. Dhondge、Deekshaputra R. Birhade、Nagorao R. Dhatrak

  DOI：10.1016/j.tetlet.2011.08.006

  日期：2011.10

  A stereodivergent route, starting from d-glyceraldehyde derivative, employing Wittig olefination–Claisen rearrangement protocol is reported for the synthesis of six novel carbahexofuranoses—carba-α-d-glucofuranose, carba-β-d-altrofuranose, carba-α-d-allofuranose, carba-β-d-idofuranose, carba-α-d-galactofuranose and carba-β-d-talofuranose in enantiomerically pure form.

  据报道，从d-甘油醛衍生物开始，采用Wittig烯烃化-Claisen重排方案的立体发散途径可合成六种新的碳呋喃呋喃糖酶，即carba-α-d-葡萄糖呋喃糖，carba-β-d-铝呋喃糖，carba-α-d-d-。对映体纯净形式的异呋喃糖，氨基甲酸酯-β-d-呋喃二糖，氨基甲酸酯-α-d-半乳糖呋喃糖和氨基甲酸酯-β-d-塔拉呋喃糖。
• Stereodivergent approach to Alzheimer's therapeutic agent ( R )-(−) and ( S )-(+)-arundic acid employing chiral 4-pentenol derivatives as building blocks
  作者：Viraj A. Bhosale、Suresh B. Waghmode

  DOI：10.1016/j.tet.2017.03.002

  日期：2017.4

  An efficient stereodivergent total synthesis of anti-Alzheimer agent (R)-(−) and (S)-(+)-arundic acid has been achieved from both chiral and nonchiral materials. This strategy features an efficient approach to separable diastereomeric C-2 chiral 4-pentenol intermediates employing proline catalysed asymmetric α-aminooxylation and [3,3] sigmatropic Claisen rearrangement are the highlights of present

  从手性和非手性材料都已经实现了抗阿尔茨海默病药物（R）-（-）和（S）-（+）-金刚烷酸的有效立体发散性全合成。该策略的特征是采用脯氨酸催化的不对称α-氨基氧基化和[3,3]σ克莱森重排的可分离非对映体C-2手性4-戊烯醇中间体的有效方法是本合成的重点。
• The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers
  作者：Mukund G. Kulkarni、Yunnus B. Shaikh、Ajit S. Borhade、Attrimuni P. Dhondge、Sanjay W. Chavhan、Mayur P. Desai、Deekshaputra R. Birhade、Nagorao R. Dhatrak、Ramesh Gannimani

  DOI：10.1016/j.tetasy.2010.08.005

  日期：2010.10

  The stereoselective synthesis of all the possible stereoisomers of bis-tetrahydrofyran alcohol, a ligand used for obtaining HIV protease inhibitors including Darunavir 1 and Brecanavir 2 has been achieved. A key intermediate 4-pentenal 5 was obtained by employing a Wittig olefination-Claisen rearrangement protocol from D-glyceraldehyde derivative 3 as a source of chirality. The 4-pentenal was readily converted in the bis-THF alcohol moiety in three steps. (C) 2010 Elsevier Ltd. All rights reserved.