2-(1,3-二恶烷-2-基)苯甲醛 | 139086-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(1,3-二恶烷-2-基)苯甲醛
• 英文名称: 2-(1,3-dioxan-2-yl)benzaldehyde
• CAS: 139086-86-5
• 化学式: C₁₁H₁₂O₃
• mdl: MFCD07700185
• 分子量: 192.214
• InChiKey: NSHMFPCAFAVGCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-(1,3-二恶烷-2-基)苯甲醛 在 盐酸 、 sodium hydroxide 、 AD-mix-α 、 potassium tert-butylate 、 四氯化锡 、 三乙胺 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 、 甲苯 、 叔丁醇 为溶剂， 生成 1-((1R,3S)-3-Hydroxymethyl-1,3-dihydro-isobenzofuran-1-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  1,3-Dihydrobenzo[ c ]furan nucleoside analogues: additional studies of the thymine derivative

  摘要：

  The detailed study of the 1,3-dihydrobenzo[c]furan derivative of thymine is reported. The lack of anti-HIV activity of this compound in cell culture experiments is shown to be related to the inability of the corresponding 5'-triphosphate derivative to interact efficiently with the reverse transcriptase. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.031
• 作为产物：
  描述：

  2-[1,3]Dioxan-2-yl-benzoic acid methyl ester 在 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 生成 2-(1,3-二恶烷-2-基)苯甲醛
  参考文献：
  名称：

  The synthesis of a porphyrin with a hydrocarbon encapsulated face

  摘要：

  The uniquely hydrocarbon-like capped porphyrin (C70H68N4), 1i, has been successfully prepared by a high dilution reaction of pyrrole with tetrakis-1,2,4,5-[pentyl-5'-(2"-formylphenyl)]-benzene 1h in the presence of boron trifluoride etherate. The aldehyde 1h was prepared by four simultaneous Wittig condensations of a phosphonium salt, 1e, with 1,2,4,5-tetraformylbenzene, followed by reduction of the double bonds with Raney nickel and deprotection with perchloric acid.

  DOI：

  10.1016/s0040-4020(01)96191-5

文献信息

• Tandem Processes in<i>C</i>-Aryl Ketenes and Ketenimines Triggered by [1,5]-Hydride-Like Migration of an Acetalic Hydrogen Atom
  作者：Angel Vidal、Marta Marin-Luna、Mateo Alajarin

  DOI：10.1002/ejoc.201301501

  日期：2014.2

  3-dioxolan-2-yl)phenyl ketenes that, under thermal conditions, smoothly underwent a [1,5]-H shift/6π-electrocyclic ring-closure sequence to give 1H-2-benzopyrans. The application of such processes to ketenes, produced by replacing the phenyl scaffolding with a thiophene ring, afforded thienopyrans. The aza-Wittig reaction of these 2-(1,3-dioxolan-2-yl)phenyl and thienyl ketenes with N-aryliminophosphoranes

  加热一系列适当取代的重氮乙酰乙酸酯产生了 2-(1,3-dioxolan-2-yl) 苯基烯酮家族，在热条件下，它们顺利地经历了 [1,5]-H 位移/6π-电环闭环序列得到 1H-2-苯并吡喃。将这些方法应用于通过用噻吩环代替苯基支架而产生的乙烯酮，得到噻吩并吡喃。这些 2-(1,3-dioxolan-2-yl) 苯基和噻吩基烯酮与 N-芳基亚氨基膦的 aza-Wittig 反应提供了类似的烯酮亚胺，它们在类似的热条件下转化为相应的 1(2H) 异喹啉酮和噻吩并吡啶酮，遵循相同类型的级联序列。
• A Highly Regio- and Stereoselective Cascade Annulation of Enals and Benzodi(enone)s Catalyzed by N-Heterocyclic Carbenes
  作者：Xinqiang Fang、Kun Jiang、Chong Xing、Lin Hao、Yonggui Robin Chi

  DOI：10.1002/anie.201007144

  日期：2011.2.18

  Three stereogenic centers in a row: The unconventional activation of enal compounds mediated by an N‐heterocyclic carbene (NHC) has generated three consecutive reactive carbon centers that undergo highly regio‐ and stereoselective annulations with di(enone)s to generate benzotricyclic products containing multiple stereogenic centers (see scheme).

  连续三个立体生成中心：由N杂环卡宾（NHC）介导的烯类化合物的非常规活化产生了三个连续的活性碳中心，这些中心经历了对二（烯酮）的高度区域和立体选择性环化反应，从而生成包含多个立体定位中心（请参阅方案）。
• Tandem processes promoted by a hydrogen shift in 6-arylfulvenes bearing acetalic units at <i>ortho</i> position: a combined experimental and computational study
  作者：Mateo Alajarin、Marta Marin-Luna、Pilar Sanchez-Andrada、Angel Vidal

  DOI：10.3762/bjoc.12.28

  日期：——

  thermally activated hydrogen shift. Structurally related fulvenes with non-cyclic acetalic units afforded mixtures of 4- and 9-alkoxybenz[f]indenes under similar thermal conditions. Mechanistic paths promoted by an initial [1,4]-, [1,5]-, [1,7]- or [1,9]-H shift are conceivable for explaining these conversions. Deuterium labelling experiments exclude the [1,4]-hydride shift as the first step. A computational

  由于热引发的级联过程的结果，在邻位带有（1,3-二氧戊环或二恶烷）-2-基取代基的6-苯基fulvenes转化为4-和9-（羟基）烷氧基取代的苯并[f]茚的混合物激活的氢转移。具有非环状缩醛单元的结构相关的富烯类在相似的热条件下提供了4-和9-烷氧基苯并[f]茚的混合物。为了解释这些转换，可以想到由初始的[1,4]-，[1,5]-，[1,7]-或[1,9] -H位移促进的机械路径。氘标记实验排除了第一步中的[1,4]-氢化物转移。一项计算研究仔细研究了从[1,5]-，[1,7]-和[1,9] -H移位开始的这些串联转化的反应通道，揭示了第一步是确定速率的步骤，并且[1，
• Domino Synthesis of Bridged Bicyclic Tetrahydro-1,2-oxazines: Access to Stereodefined 4-Aminocyclohexanols
  作者：Dwayne A. Dias、Michael A. Kerr

  DOI：10.1021/ol901454y

  日期：2009.8.20

  The intramolecular variant of the homo-[3 + 2]-dipolar cycloaddition of nitrones (generated in situ from an aldehyde and a hydroxylamine) with donor−acceptor cyclopropanes allows for the efficient synthesis of bridged tetrahydro-1,2-oxazines. This domino sequence produces adducts amenable to reductive N−O bond cleavage producing cis-1,4-aminocyclohexanols in excellent yields.

  硝酮的同型[3 + 2]-偶极环加成（从醛和羟胺原位生成）与供体-受体环丙烷的分子内变体可以有效合成桥连的四氢-1，2-恶嗪。该多米诺序列产生适合还原性N-O键裂解的加合物，以优异的产率产生顺式-1,4-氨基环己醇。
• Stereoisomeric pyrimidine nucleoside analogues based on the 1,3-dihydrobenzo[c]furan core
  作者：David F. Ewing、Nour-Eddine Fahmi、Christophe Len、Grahame Mackenzie、Alessandra Pranzo

  DOI：10.1039/b006417n

  日期：——

  efficient route is described to uracil, thymidine and cytosine derivatives of 1,3-dihydrobenzo[c]furan which are aromatic analogues of the well known antiviral 2′,3′-dideoxy-2′,3′-didehydronucleosides. These systems contain two chiral centres (corresponding to α/β and D/L centres in a furanose sugar) and a route involving application of the Sharpless asymmetric oxidation methodology allowed access to

  一种新的有效途径被描述为 尿嘧啶， 胸苷 和胞嘧啶衍生物 1,3-二氢苯并[ c ]呋喃它们是众所周知的抗病毒2′，3′-二脱氧-2′，3′-二氢核苷的芳族类似物。这些系统包含两个手性中心（对应于呋喃糖中的α/β和D / L中心），并且涉及应用Sharpless不对称氧化方法的途径允许以对映体纯净形式接近尿嘧啶衍生物的四个立体异构体。