1,2-dichloro-1,2,3,4-tetrahydronaphthalene | 31448-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2-dichloro-1,2,3,4-tetrahydronaphthalene
• 英文别名: 1,2-dichloro-1,2,3,4-tetrahydro-naphthalene；1,2-Dichlor-1,2,3,4-tetrahydro-naphthalin；1,2-Dichlorotetrahydronaphthalene
• CAS: 31448-63-2；53589-37-0
• 化学式: C₁₀H₁₀Cl₂
• 分子量: 201.095
• InChiKey: UALJNMWXCHULKF-UHFFFAOYSA-N

物化性质

• 沸点：
  296.1±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  乙醇 、 1,2-dichloro-1,2,3,4-tetrahydronaphthalene 、 alkaline earth salt of/the/ methylsulfuric acid 生成 1,2-二氢萘
  参考文献：
  名称：

  v. Braun; Kirschbaum, Chemische Berichte, 1921, vol. 54, p. 615

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4-四氢萘 在 氯 作用下， 生成 1,2-dichloro-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  v. Braun; Kirschbaum, Chemische Berichte, 1921, vol. 54, p. 615

  摘要：

  DOI：

文献信息

• Use of a fluorous bridge for diffusion controlled uptake of molecular chlorine in chlorine addition to alkenesElectronic supplementary information (ESI) available: experimental. See http://www.rsc.org/suppdata/cc/b3/b305629e/
  作者：Jernej Iskra、Stojan Stavber、Marko Zupan

  DOI：10.1039/b305629e

  日期：——

  Fluorous solvent was used for passive transport of molecular chlorine from one side of the U-tube to the other, where addition of chlorine to alkenes was quantitative and diffusion controlled.

  氟化溶剂被用于分子氯从U形管一侧到另一侧的被动传输，其中氯加成到烯烃的过程是定量的且受扩散控制。
• Convenient Chlorination with Concentrated Hydrochloric Acid in the Presence of Iodosylbenzene
  作者：Tsugio Kitamura、Yui Tazawa、Mohammad Morshed、Soichi Kobayashi

  DOI：10.1055/s-0031-1290578

  日期：2012.4

  the chlorination of indene. An efficient chlorination of β-keto esters, 1,3-diketones, and alkenes was performed conveniently with concentrated HCl in the presence of PhIO, selectively giving α-chloro-β-keto esters, 2-chloro-1,3-diketones, and 1,2-dichloroalkanes, respectively. It was suggested that the chlorination took place with (dichloroiodo)benzene generated in situ. A selective anti-addition was

  摘要 在PhIO存在下，用浓盐酸方便地对β-酮酸酯，1,3-二酮和烯烃进行有效氯化，选择性地得到α-氯-β-酮酸酯，2-氯-1,3-二酮，和1,2-二氯烷烃。建议用原位生成的（二氯碘代）苯进行氯化。在茚的氯化中观察到选择性的抗加成。 在PhIO存在下，用浓盐酸方便地对β-酮酸酯，1,3-二酮和烯烃进行有效氯化，选择性地得到α-氯-β-酮酸酯，2-氯-1,3-二酮，和1,2-二氯烷烃。建议用原位生成的（二氯碘代）苯进行氯化。在茚的氯化中观察到选择性的抗加成。
• UNIQUE HALOGEN-INDUCED CYCLIZATIONS, REAGENTS THEREFOR, AND COMPOUNDS PRODUCED THEREBY
  申请人：Snyder Scott Alan

  公开号：US20140243404A1

  公开（公告）日：2014-08-28

  This disclosure is related to halonium compounds useful for cyclization of polyenes, alkenoic acids, and alkenyl alkyl ethers, and halogenation of aromatic compounds. The synthesis of such halonium compounds, compounds made using such halonium compounds, and synthesis of natural compounds, including decalins, using the halonium compounds is also disclosed. A representative halonium compound of the disclosure is:

  本披露涉及有用于多烯环化、烯酸和烯基烷醚环化以及芳香族化合物卤代的卤化物化合物。披露了这种卤化物化合物的合成、使用这种卤化物化合物制备的化合物以及使用卤化物化合物合成天然化合物，包括蒎烯。本披露的代表性卤化物化合物为：
• Schneider, Hans-Joerg; Philippi, Klaus, Chemische Berichte, 1984, vol. 117, # 10, p. 3056 - 3074
  作者：Schneider, Hans-Joerg、Philippi, Klaus

  DOI：——

  日期：——
• 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.