2,3-bis(benzyloxy)-1,3-butadiene | 403670-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-bis(benzyloxy)-1,3-butadiene
• 英文别名: 2,3-dibenzyloxy-1,3-butadiene；2,3-(dibenzyloxy)butadiene；3-Phenylmethoxybuta-1,3-dien-2-yloxymethylbenzene
• CAS: 403670-55-3
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: WLRQWEQYYMRRBB-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  414.1±45.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-bis(benzyloxy)-1,3-butadiene 在 lithium aluminium tetrahydride 、 三苯基膦氢溴酸盐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 ((2S,3S,5R,6R)-5,6-Bis-benzyloxy-3-hydroxymethyl-5,6-dimethyl-[1,4]dioxan-2-yl)-methanol
  参考文献：
  名称：

  A New Route to Butane-1,2-diacetals and the Development of Alternative Substitution Patterns to Facilitate Differential Protection of the Products

  摘要：

  2,3-二烷氧基丁-1,3-二烯作为保护邻位二醇和α-羟基酸的试剂，其转换为相应的1,2-二乙酰基保护形式的实用性得到证实，并展示了在温和反应条件下的后续去保护过程。

  DOI：

  10.1055/s-2001-18087
• 作为产物：
  描述：

  (2R,3R)-diethyl 2,3-bis(benzyloxy)succinate 在 吡啶 、 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 2,3-bis(benzyloxy)-1,3-butadiene
  参考文献：
  名称：

  A New Route to Butane-1,2-diacetals and the Development of Alternative Substitution Patterns to Facilitate Differential Protection of the Products

  摘要：

  2,3-二烷氧基丁-1,3-二烯作为保护邻位二醇和α-羟基酸的试剂，其转换为相应的1,2-二乙酰基保护形式的实用性得到证实，并展示了在温和反应条件下的后续去保护过程。

  DOI：

  10.1055/s-2001-18087

文献信息

• Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives
  作者：Steven V. Ley、Elena Diez、Darren J. Dixon、Richard T. Guy、Patrick Michel、Gillian L. Nattrass、Tom D. Sheppard

  DOI：10.1039/b412788a

  日期：——

  The preparation of butane-2,3-diacetal protected glycolic acid and related systems is described together with highly selective alkylation reactions of (R,R) and (S,S) butanediacetal protected glycolic acid. These compounds are readily deprotected to give enantiopure alpha-hydroxyacids, alpha-hydroxyesters or alpha-hydroxyamides by suitable choice of conditions.

  描述了由2,3-二缩醛丁烷保护的乙醇酸的制备方法和相关系统，以及（R，R）和（S，S）丁二缩醛保护的乙醇酸的高度选择性烷基化反应。这些化合物可容易地脱保护，得到对映体纯的α-羟基酸，由条件适当选择的α-羟基酯或α-羟基酰胺。
• Reactive diene for synthesis of substituted catechols
  作者：Benjamin J. Compton、David S. Larsen、Lesley Larsen、Rex T. Weavers

  DOI：10.1016/j.tetlet.2007.11.085

  日期：2008.1

  (2R,3R)-2,3-Dimethoxy-2,3-dimethyl-5,6-dimethylene-1,4-dioxane has been synthesized and is a highly efficient diene in Diels–Alder reactions. Reaction with acetylenic dienophiles provides a simple route to substituted catechols. Reactions with some ethylenic dienophiles are also reported.

  （2 R，3 R）-2,3-二甲氧基-2,3-二甲基-5,6-二亚甲基-1,4-二恶烷已经合成，是Diels-Alder反应中的高效二烯。与炔属二烯亲和剂的反应提供了取代邻苯二酚的简单途径。还报道了与一些烯属二烯亲生物的反应。
• Macrocycles
  申请人：LUMIPHORE, INC.

  公开号：US10273256B2

  公开（公告）日：2019-04-30

  The invention relates to chemical compounds and complexes that can be used in therapeutic and diagnostic applications.

  本发明涉及可用于治疗和诊断的化合物和复合物。
• Asymmetric Diels−Alder Reactions of Unsaturated β-Ketoesters Catalyzed by Chiral Ruthenium PNNP Complexes
  作者：Christoph Schotes、Antonio Mezzetti

  DOI：10.1021/ja910039e

  日期：2010.3.24

  Cyclic alpha-unsaturated beta-ketoesters undergo cycloaddition with di- and trisubstituted butadienes to give tetrahydro-1-indanone derivatives with up to 93% ee in the presence of a ruthenium catalyst formed by activation of [RuCl(2)(PNNP)] with (Et(3)P)PF(6) (2 equiv) (PNNP = (1S,2S)-N,N'-bis[o-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine). The protocol has been used to prepare the estrone derivative (8R, 13S, 14S)-13-tert-butoxycarbonyl-3-methoxy-7,8,1 2,13,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17(14H)-one as a single diastereoisomer with 85% yield and 99% ee after one crystallization step. Its absolute configuration, which has been determined by X-ray diffraction after reduction to the alcohol and esterification with camphanic chloride, is in agreement with the attack of the diene onto the open enantioface of the beta-keto ester (O-O) in the ruthenium complex [Ru(O-O)(PNNP)](2+), whose X-ray structure has been determined.
• Asymmetric Diels–Alder and Ficini Reactions with Alkylidene β-Ketoesters Catalyzed by Chiral Ruthenium PNNP Complexes: Mechanistic Insight
  作者：Christoph Schotes、Martin Althaus、Raphael Aardoom、Antonio Mezzetti

  DOI：10.1021/ja210372u

  日期：2012.1.18

  Hydride abstraction from the beta-position of the enolato ligand of the previously reported complex [Ru(3a-H)(PNNP)]PF6 (5a; 3a-H is the enolate of 2-tert-butoxy-carbonylcyclopentanone) with (Ph3C)PF6 gives the dicationic complex [Ru(6a)(PNNP)(2+) (7a) as a single diastereoisomer, which contains the unsaturated beta-ketoester 2-tert-butoxycarbonyl-2-cyclopenten-1-one (6a) as a chelating ligand. The methyl analogue 2-methoxycarbonylcyclopentanone (3b) gives [Ru(3b-H)(PNNP)]PF6 as a mixture of noninterconverting diastereoisomers (ester group of 3b trans to P, 5b; or to N, 5c), which were separated by column chromatography. Hydride abstraction from 5b (or 5c) yields diastereomerically pure [Ru(6b)(PNNP)](2+) (7b or 7c). Complexes 7b and 7c do not interconvert at room temperature in CD2CI2 and form opposite enantiomers of the Diets Alder adduct upon reaction with Dane's diene (1 equiv). X-ray studies of 7a, 5b, and 5c give insight into the origin of enantioselection and the sense of asymmetric induction in the previously reported asymmetric Diels-Alder and Ficini cycloaddition reactions with 2,3-disubstituted butadienes and ynamides, respectively. Stoichiometric reactions (substrate coordination, cycloaddition, and product displacement) between [Ru-(OEt2)(2)(PNNP)](2+) (2), 6b (or 6a), and Dane's diene (15, to give estrone derivatives) or N-benzyl-N-(cyclohexylethynyl)-4-methylbenzenesulfonamide (17, to give cyclobutenamides) suggest that product displacement from the catalyst is turnover limiting.