5-bromo-1,2-dihydronaphthalene | 1451012-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-bromo-1,2-dihydronaphthalene
• CAS: 1451012-53-5
• 化学式: C₁₀H₉Br
• 分子量: 209.085
• InChiKey: SQXHZYUYPBKDFO-UHFFFAOYSA-N

物化性质

• 沸点：
  267.2±29.0 °C(Predicted)
• 密度：
  1.434±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-bromo-1,2-dihydronaphthalene 在 copper(I) oxide 、 (+)-1,2-双((2S,5S)-2,5-二苯基膦)乙烷 、 1,10-菲罗啉 、 potassium tert-butylate 、 亚磷酸二乙酯 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 生成 (R)-8-(二苯基膦)-1,2,3,4-四氢萘-1-胺
  参考文献：
  名称：

  COPPER CATALYZED HALOGENATON AND REACTION PRODUCTS

  摘要：

  一种Cu(I)催化的1,3-卤迁移反应有效地通过将卤素从sp2转移到苄基碳来循环利用一个活化基团，具有良好的对映选择性并伴随Ar-卤键的硼化反应。所得的对映富集的苄基卤化物可以在同一容器中在各种条件下反应，形成额外的碳-杂原子或碳-碳键，同时保持高的ee。该反应可用于高效制备新型化合物和制备治疗剂和催化剂配体的中间体。

  公开号：

  US20140371480A1
• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘酚 在 正丁基锂 、 甲基磺酰氯 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 5-bromo-1,2-dihydronaphthalene
  参考文献：
  名称：

  Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes

  摘要：

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.

  DOI：

  10.1055/s-0033-1338865

文献信息

• [EN] PREPARATION AND APPLICATION METHOD OF HETEROCYCLIC COMPOUND AS KRAS INHIBITOR<br/>[FR] PRÉPARATION ET PROCÉDÉ D'APPLICATION D'UN COMPOSÉ HÉTÉROCYCLIQUE EN TANT QU'INHIBITEUR DE KRAS<br/>[ZH] 作为KRAS抑制剂的杂环化合物的制备及其应用方法
  申请人：SHANGHAI KECHOW PHARMA INC

  公开号：WO2021219072A1

  公开（公告）日：2021-11-04

  式(I)的化合物或其药学上可接受的盐、前药、互变异构体或立体异构体和溶剂化物，这类化合物可用于治疗哺乳动物中癌症和炎症。还公开了式(I)化合物的制备方法以及包含所述化合物的药物组合物。
• Verification of the Major Metabolic Oxidation Path for the Naphthoyl Group in Chemoattractant Receptor-Homologous Molecule Expressed on Th2 Cells (CRTh2) Antagonist 2-(2-(1-Naphthoyl)-8-fluoro-3,4-dihydro-1<i>H</i>-pyrido[4,3-<i>b</i>]indol-5(2<i>H</i>)-yl)acetic Acid (Setipiprant/ACT-129968)
  作者：Philippe Risch、Thomas Pfeifer、Jerome Segrestaa、Heinz Fretz、Julien Pothier

  DOI：10.1021/acs.jmedchem.5b00824

  日期：2015.10.22

  Various racemic and enantioenriched (trans)-X,Y-dihydroxy-X,Y-dihydronaphthoyl analogues as well as X-hydroxy-naphthoyl analogues of CRTh2 antagonist 2-(2-(1-naphthoyl)-8-fluoro-3,4-dihydro-1H-pyrido [4,3-b]indol-5(2H)-yl) acetic acid (1, Setipiprant/ACT-129968) were synthesized in order to gain insight into regio- and enantioselectivity of the metabolic oxidation of 1 and to verify the structures of four metabolites that were proposed earlier in a clinical ADME study. Analytical data of the synthetic standards were compared with data from samples of biological origin. The two major metabolites M7 and M9 were unambiguously verified as 2-(2-((trans)-3,4-dihydroxy-3,4-dihydronaphthalene-1-carbony1)- and 242-((trans)-5,6-dihydroxy-5,6-dihydronaphthalene-1-carbonyl)-8-fluoro-3,4-dihydro-1H-pyrido [4,3-b]indol-5 (2H)-yl) acetic acid, respectively, each composed of two enantiomers with 68% and 44% ee in favor of (+)-(3S,4S)-M7 and (+)-(5S,6S)-M9, respectively. Likewise, minor metabolites M3 and M13 were identified as 2-(8-fluoro-2-(5-hydroxy-1-naphthoyl) and 2-(8-fluoro-2-(4-hydroxy-1-naphthoyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-5-yl)acetic acid, respectively.
• US9382279B2
  申请人：——

  公开号：US9382279B2

  公开（公告）日：2016-07-05
• Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes
  作者：Scott Snyder、Alexandria Brucks、Daniel Treitler、Shu-An Liu

  DOI：10.1055/s-0033-1338865

  日期：——

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.
• COPPER CATALYZED HALOGENATON AND REACTION PRODUCTS
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20140371480A1

  公开（公告）日：2014-12-18

  A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring a halogen from an sp 2 to a benzylic carbon with good enantioselectivity and concomitant borylation of the Ar-halo bond. The resulting enantio-enriched benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom or carbon-carbon bond while maintaining high ee. The reaction can be used to efficiently prepare novel compounds and intermediates for the preparation of therapeutics and ligands for catalysis.

  一种Cu(I)催化的1,3-卤迁移反应有效地通过将卤素从sp2转移到苄基碳来循环利用一个活化基团，具有良好的对映选择性并伴随Ar-卤键的硼化反应。所得的对映富集的苄基卤化物可以在同一容器中在各种条件下反应，形成额外的碳-杂原子或碳-碳键，同时保持高的ee。该反应可用于高效制备新型化合物和制备治疗剂和催化剂配体的中间体。