1-(phenylsulfonyl)-3-formaldehyde ethylene glycol acetal | 403597-66-0

• 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: 1-(phenylsulfonyl)-3-formaldehyde ethylene glycol acetal
• 英文别名: 1-(phenylsulfonyl)indole-3-carbaldehyde ethylene acetal；1-(Benzenesulfonyl)-3-(1,3-dioxolan-2-yl)indole
• CAS: 403597-66-0
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: HKEPSEFQTQNHQL-UHFFFAOYSA-N

物化性质

• 沸点：
  546.6±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(phenylsulfonyl)-3-formaldehyde ethylene glycol acetal 在 三氟化硼乙醚 、 仲丁基锂 、 对苯二酚 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 6.25h， 生成 4-(phenylsulfonyl)-4H-furo<3,4-b>indole
  参考文献：
  名称：

  An Efficient Synthesis of 4-(Phenylsulfonyl)-4H-furo[3,4-b]indoles

  摘要：

  The fused heterocycle 4-(phenylsulfonyl)-4H-furo-[3,4-b]indole, which is an indole-2,3-quinodimethane synthetic analogue, is prepared in five steps from indole in 46% yield. A similar sequence is used to synthesize C-3 derivatives (3-methyl, 3-phenyl, and 3-heptyl). Thus, indole-3-carbaldehyde (1) is protected as the N-phenylsulfonyl derivative 2 and converted to the ethylene acetal 6. Lithiation at C-2 followed by treatment with an aldehyde affords the expected hydroxy acetals 7 and S. Exposure to acid effects cyclization to the furoindoles 5 and 9. Furthermore, C-1 lithiation of furo[3,4-b]indole 9c followed by treatment with methyl iodide affords disubstituted furo[3,4-b]indole 10.

  DOI：

  10.1021/jo010938q
• 作为产物：
  描述：

  3-吲哚甲醛 在 sodium hydroxide 、 四丁基硫酸氢铵 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 18.0h， 生成 1-(phenylsulfonyl)-3-formaldehyde ethylene glycol acetal
  参考文献：
  名称：

  An Efficient Synthesis of 4-(Phenylsulfonyl)-4H-furo[3,4-b]indoles

  摘要：

  The fused heterocycle 4-(phenylsulfonyl)-4H-furo-[3,4-b]indole, which is an indole-2,3-quinodimethane synthetic analogue, is prepared in five steps from indole in 46% yield. A similar sequence is used to synthesize C-3 derivatives (3-methyl, 3-phenyl, and 3-heptyl). Thus, indole-3-carbaldehyde (1) is protected as the N-phenylsulfonyl derivative 2 and converted to the ethylene acetal 6. Lithiation at C-2 followed by treatment with an aldehyde affords the expected hydroxy acetals 7 and S. Exposure to acid effects cyclization to the furoindoles 5 and 9. Furthermore, C-1 lithiation of furo[3,4-b]indole 9c followed by treatment with methyl iodide affords disubstituted furo[3,4-b]indole 10.

  DOI：

  10.1021/jo010938q

文献信息

• A New Concise Strategy for Synthesis of Dibenzo[<i>b,f</i>]thiepins and Related Fused Symmetrical Thiepin Derivatives
  作者：Hamid Shirani、Tomasz Janosik

  DOI：10.1021/jo701627g

  日期：2007.11.1

  A new strategy for preparation of dibenzo[b,f]thiepins and related fused systems in good overall yields is described, featuring ortho-metalation of aromatic or heterocyclic aldehyde acetals followed by treatment with bis(phenylsulfonyl) sulfide for construction of the required bis(aryl)- or bis(heteroaryl) sulfide precursors, which were thereafter subjected to deacetalization, and finally McMurry coupling

  描述了一种以较高的总收率制备二苯并[ b，f ]噻吩并相关的熔融体系的新策略，其特征在于将芳族或杂环醛缩醛进行邻位金属化，然后用双（苯磺酰基）硫化物处理以构建所需的双（芳基）或双（杂芳基）硫化物前体，然后对其进行脱缩醛化，最后进行McMurry偶联作为成环步骤。
• Synthesis of an azide-tethered 4H-furo[3,4-b]indole
  作者：Daniel J. Keavy、Yanbing Liu、Gordon W. Gribble

  DOI：10.24820/ark.5550190.p011.099

  日期：——

  We describe the synthesis of a novel azide-tethered 4H-furo[3,4-b]indole as a putative intermediate for a projected route to the 2-acylindole class of indole alkaloids. N H N H N H N O N3 Me

  我们描述了一种新型叠氮化物束缚的 4H-呋喃 [3,4-b] 吲哚的合成，作为推定的中间体，用于 2-酰基吲哚类吲哚生物碱的预计路线。NHNHNHNO N3 Me
• Expedient Synthesis of Highly Functionalised Cyclic Imines
  作者：Thomas Moss

  DOI：10.1055/s-0034-1379918

  日期：——

  Aryl- and heteroaryl fused cyclic imines are obtained from the starting acetal via a directed metallation-alkylation-condensation sequence using cyclic sulfamidates as the electrophile. A variety of aromatics and heteroaromatics are demonstrated to be applicable to this methodology, which produces highly versatile cyclic imine building blocks for drug discovery and total synthesis programmes.
• New syntheses of unsymmetrical thiepins and their selenium analogues
  作者：Hamid Shirani、Jan Bergman、Tomasz Janosik

  DOI：10.1016/j.tet.2009.08.014

  日期：2009.10

  New routes toward fused thiepins and their selenium analogues are described, wherein initial cleavage of suitable diaryl disulfides or selenides bearing masked aldehyde functionalities with an N-protected and metalated indole-3-carbaldehyde acetal or a lithiated 2-bromobenzaldehyde acetal derivative gave a set of unsymmetrical diacetals. Subsequent deacetalization, followed by McMurry coupling, afforded the target unsymmetrical thiepins and selenepins. (C) 2009 Elsevier Ltd. All rights reserved.
• LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
  申请人：Buckman Brad O.

  公开号：US20130072449A1

  公开（公告）日：2013-03-21

  Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.