2-chloro-1,2,3,4-tetrahydro-[1]naphthol | 90919-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-chloro-1,2,3,4-tetrahydro-[1]naphthol
• 英文别名: 2-Chlor-1-oxy-1.2.3.4-tetrahydro-naphthalin；2-Chlor-1,2,3,4-tetrahydro-[1]naphthol；2-Chlor-1-oxy-tetralin；2-Chlor-tetralol-(1)；2-Chloro-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS: 90919-04-3
• 化学式: C₁₀H₁₁ClO
• mdl: MFCD20545814
• 分子量: 182.65
• InChiKey: FDPHJPOUBLOBJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  332.1±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  哌啶 、 2-chloro-1,2,3,4-tetrahydro-[1]naphthol 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Straus; Rohrbacher, Chemische Berichte, 1921, vol. 54, p. 57

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-二氢萘 在 盐酸 、 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以79%的产率得到2-chloro-1,2,3,4-tetrahydro-[1]naphthol
  参考文献：
  名称：

  钌基人工酶有效地将烯烃转化为氯醇

  摘要：

  需要人造酶来催化非天然反应。在这里，通过在运输蛋白NikA中嵌入新型Ru络合物来开发杂化催化剂。蛋白质支架激活...

  DOI：

  10.1039/c6cc08873b

文献信息

• v. Braun; Weissbach, Chemische Berichte, 1930, vol. 63, p. 3052,3055
  作者：v. Braun、Weissbach

  DOI：——

  日期：——
• Are Mn^IV Species Involved in Mn(Salen)-Catalyzed Jacobsen−Katsuki Epoxidations? A Mechanistic Elucidation of Their Formation and Reaction Modes by EPR Spectroscopy, Mass-Spectral Analysis, and Product Studies:  Chlorination versus Oxygen Transfer
  作者：Waldemar Adam、Cordula Mock-Knoblauch、Chantu R. Saha-Möller、M. Herderich

  DOI：10.1021/ja0005082

  日期：2000.10.1

  EPR and ESI-MS/MS evidence is presented that in the absence of an olefinic substrate the reaction between the Mn-III(salen) complexes Al (X = Cl) and A2 (X = PF6) and PhIO or NaOCl as oxygen sources leads to paramagnetic Mn-IV(salen) complexes. Depending on the solvent and the counterion, two distinct Mn-IV (salen) complexes intervene. In CH2Cl2, regardless of the counterion, a ClOMnIV(salen) complex (B1) and a HOMnIV(salen) complex (B1') are formed by Cl and H atom abstraction from CH2Cl2, and the latter deprotonates to the neutral OMnIV(salen) complex (B2). In EtOAc as solvent, only the complex B2 is obtained from Al (X = Cl), presumably by inner-sphere electron transfer from the chloride ion. The Mn-IV(salen) complexes display the following reaction modes toward 1,2-dihydronaphthalene (1), styrene (2), and the radical probe 3 as substrates: Complex B1 chlorinates the olefins 1/2 through an electrophilic :pathway to yield the 1,2-dichloro adducts 1a/2a and the chlorohydrins 1b/2b (nucleophilic trapping of the initially formed benzylic cation), while with olefin 3 the ring-opened dichloro product 3a results. Complex B2, however, epoxidizes these olefins through a radical pathway, as evidenced by the formation of isomerized stilbene oxide 4c (cis/trans ratio 36: 64) from cis-stilbene (4). The relevance of these paramagnetic Mn-IV(salen) species in Jacobsen-Katsuki catalytic epoxidations is scrutinized.